OPTIMARK TECHNOLOGIES INC
10-12G/A, EX-3.1, 2000-06-16
BUSINESS SERVICES, NEC
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                                                                     Exhibit 3.1

                          CERTIFICATE OF INCORPORATION
                                       OF
                             OPTIMARK HOLDINGS, INC.

       The undersigned, for the purpose of organizing a corporation under the
General Corporation Law of the State of Delaware, certifies the following:

       1.     Name. The name of the Corporation is: OptiMark Holdings, Inc. (the
"Corporation").

       2.     Registered Office; Registered Agent. The registered office of the
Corporation is located at 1209 Orange Street, Corporation Trust Center,
Wilmington, New Castle County, Delaware 19801. The name of its registered agent
at such address is The Corporation Trust Company.

       3.     Term. The Corporation shall have perpetual existence.

       4.     Purposes. The nature, objects and purposes of the business to be
transacted by the Corporation shall be to engage in any lawful activity for
which corporations may be organized under the Delaware General Corporation Law.

       5.     Powers. In furtherance of the foregoing purposes, the Corporation
shall have and may exercise all of the rights, powers and privileges now or
hereafter conferred upon corporations organized under the Delaware General
Corporation Law. In addition, it may do everything necessary, suitable or proper
for the accomplishment of any of its corporate purposes.

       6.     Shares of Stock. The total number of shares of capital stock which
the Corporation is authorized to issue is one hundred ninety million
(190,000,000), consisting of one hundred fifty million (150,000,000) shares of
common stock, one cent ($0.01) par value per share ("Common Stock"), and forty
million (40,000,000) shares of preferred stock, one cent ($0.01) par value per
share ("Preferred Stock").

              (a)    Preferred Stock. The Board of Directors of the Corporation
is expressly granted the authority to issue the Preferred Stock in one or more
classes or series, and to fix, by one or more resolutions from time to time, the
designations, powers, preferences and rights, and the qualifications,
limitations and restrictions, of such classes and series of the Preferred Stock.

              (b)    Common Stock. One million five hundred thousand (1,500,000)
shares of authorized Common Stock shall be designated as Nonvoting Common Stock.
To the maximum extent permitted by law, the shares of Nonvoting Common Stock
shall have no voting rights whatsoever on any matters submitted to a vote or
consent of the stockholders of the Corporation. The balance of the authorized
Common Stock shall be voting Common Stock, the holders of which shall have the
right to vote for the election of directors and on all other matters submitted
to a vote of the stockholders generally,


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with each share entitled to one vote. Except as described in the preceding two
sentences with respect to voting rights, each share of Common Stock shall be
equal to every other share of Common Stock for all purposes. Subject to the
prior rights and privileges of the holders of Preferred Stock (if any), upon the
voluntary liquidation, dissolution or winding up of the Corporation, the net
assets of the Corporation shall be distributed pro rata to the holders of the
Common Stock.

              7.     Election of Directors; No Cumulative Voting. The Board of
Directors shall consist of one or more members, with the number specified or
fixed in accordance with the bylaws of the Corporation. Members of the Board of
Directors may be elected either by written ballot or by voice vote. The
stockholders of the Corporation shall not have cumulative voting rights in the
election of directors or with respect to any other matter.

              8.     Adoption, Amendment or Repeal of Bylaws. In furtherance of
and not in limitation of the powers conferred by laws of the State of Delaware,
the Board of Directors is expressly authorized to adopt, amend and repeal the
bylaws of the Corporation; provided that any bylaws adopted or amended by the
Board of Directors may be amended or repealed, and any bylaws may be adopted, by
the stockholders of the Corporation.

              9.     Restrictions on Transfer of Stock. The Corporation is
granted the right to impose such restrictions on the transfer of the
Corporation's stock as the Board of Directors deems necessary, advisable or
proper.

              10.    Elimination of Certain Liability of Directors. A director
of the Corporation shall not be personally liable to the Corporation or its
stockholders for monetary damages for breach of fiduciary duty as a director,
except for liability (a) for any breach of the director's duty of loyalty to the
Corporation or its stockholders, (b) for acts or omissions not in good faith or
which involve intentional misconduct or a knowing violation of law, (c) in
respect of certain unlawful dividend payments or stock redemptions or
repurchases, or (d) for any transaction from which the director derived an
improper personal benefit. Any repeal or modification of the foregoing sentence
shall not adversely affect any right or protection of a director of the
Corporation existing hereunder with respect to any act or omission occurring
prior to such repeal or modification.

              11.    Indemnification and Insurance. The Corporation shall
indemnify, to the maximum extent permitted by law, any person who is or was a
director or officer of the Corporation or is or was serving at the request of
the Corporation as a director, officer, partner, trustee, employee or agent of
another corporation or of a partnership, joint venture, trust or other
enterprise, against any claim, liability or expense arising against or incurred
by such person as a result of actions reasonably taken by him at the direction
of the Corporation or in connection with his service to the Corporation. Any
person who is not covered by the foregoing sentence and who is or was an
employee or agent of the Corporation may be indemnified by the Corporation to
the maximum extent permitted by

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law as authorized by the Board of Directors from time to time. The Corporation
further shall have the authority to purchase and maintain insurance, at the
Corporation's expense, providing for indemnification up to the maximum extent
permitted by law.

              12.    Interested Transactions. The fact that a director or
officer of the Corporation is directly or indirectly interested in or connected
with any person or entity (a) employed by the Corporation to render or perform a
service or (b) from or to whom the Corporation may buy or sell merchandise or
other property, shall not (except as provided under the Delaware General
Corporation Law) prohibit the Corporation from employing such person or from
dealing with such person on customary terms with competitive rates of
compensation, and neither the Corporation nor any stockholder shall have any
claims or rights in any obligation, compensation or income payable to such
person.

              13.    Compromises/Arrangements. Whenever a compromise or
arrangement is proposed between the Corporation and its creditors or any class
of them and/or between the Corporation and its stockholders or any class of
them, any court of equitable jurisdiction within the State of Delaware may, on
the application in a summary way of the Corporation or of any creditor or
stockholder thereof or on the application of any receiver or receivers appointed
for the Corporation under the provisions of Section 291 of the Delaware General
Corporation Law, or on the application of trustees in dissolution or any
receiver or receivers appointed for the Corporation under the provisions of
Section 279 of the Delaware General Corporation Law, order a meeting of the
creditors or class of creditors, and/or of the stockholders or class of
stockholders of the Corporation, as the case may be, to be summoned in such
manner as such court directs. If a majority in number representing three-fourths
in value of the creditors or class of creditors, and/or of the stockholders or
class of stockholders of the Corporation, as the case may be, agree to any
compromise or arrangement and to any reorganization of the Corporation as a
consequence of such compromise or arrangement, the said compromise or
arrangement and the said reorganization shall, if sanctioned by the court to
which the application has been made, be binding on all the creditors or class of
creditors, and/or on all the stockholders or class of stockholders, of the
Corporation as the case may be, and also on the Corporation.

              14.    Reservation of Rights. The Corporation reserves the right
at any time, and from time to time, to amend, alter, change or repeal any
provision contained in this Certificate of Incorporation, and other provisions
authorized by the laws of the State of Delaware at the time in force may be
added or inserted, in the manner now or hereafter prescribed by law; and all
rights, preferences and privileges of whatsoever nature conferred upon
stockholders, directors or any other persons whomsoever by and pursuant to this
Certificate of Incorporation in its present form or as hereafter amended are
granted subject to the rights reserved in this Article 14.

              15.    Incorporator. The name and mailing address of the
incorporator is Andrew J. Graf, c/o Milbank, Tweed, Hadley & McCloy LLP, One
Chase Manhattan Plaza, New York, New York 10005.


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       WITNESS my signature this 19th day of May, 2000.

                                             By:  /s/ Andrew J. Graf
                                                  Sole Incorporator






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                      CERTIFICATE OF POWERS, DESIGNATIONS,

                          PREFERENCES AND RIGHTS OF THE
               SERIES A CONVERTIBLE PARTICIPATING PREFERRED STOCK,

                            PAR VALUE $.01 PER SHARE

             Pursuant to Section 151 of the General Corporation Law
                            of the State of Delaware

       The following resolution was duly adopted by the Board of Directors of
OptiMark Holdings, Inc., a Delaware corporation (the "Corporation"), pursuant to
the provisions of Section 151 of the General Corporation Law of the State of
Delaware, effective as of June 9, 2000, by unanimous written consent of the
Board of Directors.

       WHEREAS, the Board of Directors is authorized, within the limitations and
restrictions stated in the Certificate of Incorporation of the Corporation, to
provide by resolution or resolutions for the issuance of shares of Preferred
Stock, par value $.01 per share, of the Corporation, in one or more series with
such voting powers, full or limited, or without voting powers, and such
designations, preferences and relative, participating, optional or other special
rights, and qualifications, limitations or restrictions as shall be stated and
expressed in the resolution or resolutions providing for the issuance thereof
adopted by the Board of Directors, and as are not stated and expressed in the
Certificate of Incorporation, or any amendment thereto, including (but without
limiting the generality of the foregoing) such provisions as may be desired
concerning voting, redemption, dividends, dissolution or the distribution of
assets and such other subjects or matters as may be fixed by resolution or
resolutions of the Board of Directors under the General Corporation Law of the
State of Delaware; and

       WHEREAS, it is the desire of the Board of Directors, pursuant to its
authority as aforesaid, to authorize and fix the terms of a series of preferred
stock and the number of shares constituting such series.

       NOW, THEREFORE, BE IT RESOLVED:

       1.     Designation and Number of Shares. There shall be hereby
established a series of Preferred Stock designated as "Series A Convertible
Participating Preferred Stock" (the "Series A Preferred Stock"). The authorized
number of shares of Series A Preferred Stock shall be 3,222,068.

       2.     Rank. The Series A Preferred Stock shall, with respect to
distributions of assets and rights upon the liquidation, winding up and
dissolution of the Corporation, rank senior to (a) all classes of common stock
of the Corporation (including, without limitation, the common stock, par value
$.01 per share, of the Corporation) (the

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"Common Stock") and (b) each other class or series of Capital Stock of the
Corporation hereafter created which does not expressly rank pari passu with or
senior to the Series A Preferred Stock (the "Junior Stock").

       3.     Dividends. Beginning on the date of issuance of the Series A
Preferred Stock, if the Board of Directors of the Corporation shall declare a
dividend or make any other distribution (including, without limitation, in cash,
evidences of indebtedness of the Corporation or another issuer, securities of
the Corporation or another issuer or other property or assets), to holders of
shares of Common Stock, then the holder of each share of Series A Preferred
Stock shall be entitled to receive, out of funds legally available therefor, a
dividend or distribution in an amount equal to the amount of such dividend or
distribution received by a holder of the number of shares of Common Stock for
which such share of Series A Preferred Stock is convertible on the record date
for such dividend or distribution. Any such amount shall be paid to the holders
of shares of Series A Preferred Stock at the same time such dividend or
distribution is made to holders of Common Stock.

       4.     Liquidation Preference.

              (a)    Subject to paragraph 4(b) below, in the event of any
voluntary or involuntary liquidation, dissolution or winding up of the
Corporation, the holders of shares of Series A Preferred Stock then outstanding
shall be entitled to be paid for each share of Series A Preferred Stock held
thereby, out of the assets of the Corporation available for distribution to its
stockholders, before any payment shall be made or any assets distributed to the
holders of any shares of Junior Stock, an amount (the following (i) and (ii)
together, the "Liquidation Amount") equal to (i) $7.33 per share (the
"Liquidation Preference") plus (ii) all declared and unpaid dividends thereon to
the date fixed for liquidation, dissolution or winding up. If the assets of the
Corporation are not sufficient to pay in full the foregoing Liquidation Amount
to the holders of outstanding shares of the Series A Preferred Stock, then the
holders of all shares of Series A Preferred Stock shall share ratably in such
distribution of assets in accordance with the amount that would be payable on
such distribution if the amounts to which the holders of outstanding shares of
Series A Preferred Stock are entitled were paid in full.

              (b)    After the holders of all shares of Series A Preferred Stock
shall have been allocated in full the amounts to which they are entitled under
paragraph 4(a), each holder of Series A Preferred Stock and Common Stock shall
be entitled to receive such holder's pro rata share, based on the number of
shares of Common Stock held by such holder and assuming conversion of all shares
of Series A Preferred Stock into Common Stock ("Pro Rata Share"), of the
remaining assets of the Corporation available for distribution; provided,
however, that if the fair value per share of Common Stock (assuming conversion
of all shares of Series A Preferred Stock into Common Stock) of the entire
assets of the Corporation legally available for distribution (without deduction
for any preferential amount which may be payable to holders of the Series A
Preferred Stock pursuant to paragraph 4(a)) (the "Common Stock Fair Value", as
determined pursuant to subparagraph (e) below) equals or exceeds the Conversion
Price

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then in effect multiplied by five (5), then each holder of Series A Preferred
Stock and Common Stock shall be entitled to receive such holder's Pro Rata Share
of such entire assets, and the holders of Series A Preferred Stock shall not
receive any prior payment of any preferential amount pursuant to paragraph 4(a).
Notwithstanding anything contained in this paragraph 4 to the contrary, if the
Common Stock Fair Value is less than the Conversion Price then in effect
multiplied by five (5), then the holders of Series A Preferred Stock shall not
be entitled to receive an amount greater than the Common Stock Fair Value
multiplied by five (5).

              (c)    Written notice of such liquidation, dissolution or winding
up, stating a payment date, the amount of the payment as determined pursuant to
this paragraph 4 and the place where such amount shall be payable, shall be
delivered in person, mailed by certified or registered mail, return receipt
requested, mailed by overnight mail or sent by telecopier, not less than ten
(10) days prior to the payment date stated therein, to the holders of record of
the Series A Preferred Stock, such notice to be addressed to each such holder at
its address as shown by the records of the Corporation.

              (d)    For purposes of paragraph 2 and this paragraph 4, a
voluntary or involuntary liquidation, dissolution or winding up of the affairs
of the Corporation shall include (i) the voluntary sale, conveyance, exchange or
transfer to another Person of all or substantially all of the assets of the
Corporation and (ii) (x) the merger or consolidation of the Corporation with or
into one or more Persons or (y) the merger or consolidation of one or more
Persons with or into the Corporation, if, in the case of (x) or (y), the
stockholders of the Corporation prior to such merger or consolidation do not
retain at least a majority of the voting power of the surviving Person and (iii)
a transaction or a series of related transactions (other than a public offering
of the Corporation's securities) in which the Corporation issues shares of
Capital Stock with the result that the stockholders of the Corporation prior to
such issuance do not retain at least a majority of the voting power of the
Corporation after giving effect to such transaction (each of the foregoing (i),
(ii) and (iii) being referred to hereinafter as a "Liquidation Event"). For the
purposes of the foregoing, the exchange of securities or other consideration of
the surviving Person or an affiliate thereof for securities of the Corporation
shall be deemed to constitute the distribution of assets of the Corporation upon
a Liquidation Event.

              (e)    The fair value of the assets to be distributed or exchanged
(to the extent that distributions are not made in cash) in the event of a
Liquidation Event shall be determined by the Board of Directors in good faith;
provided, however, that any securities to be delivered to the holders of any
class or series of the Corporation's capital stock under this paragraph 4 shall
be valued as follows:

                     (i)    Securities that do not constitute "restricted
securities," as such item is defined in Rule 144(a)(3) promulgated under the
Securities Act:

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                            (A)    If traded on a securities exchange, the value
shall be deemed to be the average of the closing prices of the securities on
such exchange over the 30-day period ending three (3) days prior to the date of
distribution;

                            (B)    If actively traded over-the-counter, the
value shall be deemed to be the average of the closing bid prices over the
30-day period ending three (3) days prior to the date of distribution;

                            (C)    If there is no active public market, the
value shall be the fair market value thereof, as mutually determined by the
Corporation and the holders of not less than a majority of the then outstanding
shares of Series A Preferred Stock.

                            (D)    If fair market value cannot be determined
pursuant to clause (C) above, the Corporation and the holders of not less than a
majority of the then outstanding shares of Series A Preferred Stock shall each
appoint one (1) independent third party and such two persons shall in turn
select a third person, which group of three persons shall then determine the
fair market value thereof.

                     (ii)   The method of valuation of securities subject
to investment letter or other restrictions on free marketability that are of the
same class or series as securities that are publicly traded shall be to make an
appropriate discount from the market value determined as set forth above in
clauses (i)(A) or (i)(B) to reflect the appropriate fair market value thereof,
as mutually determined by the Corporation and the holders of a majority of the
then outstanding shares of Series A Preferred Stock, or if applicable, shall be
in accordance with clauses (i)(C) or (i)(D), giving appropriate weight, if any,
to such restriction.

              5.     Redemption. The shares of Series A Preferred Stock shall
not be redeemed or subject to redemption, whether at the option of the
Corporation or any holder thereof, or otherwise.

              6.     Voting Rights; Election of Directors. So long as the Series
A Preferred Stock is outstanding, each share of Series A Preferred Stock shall
entitle the holder thereof to vote, in person or by proxy, at a special or
annual meeting of stockholders, on all matters entitled to be voted on by
holders of Common Stock voting together as a single class with other shares
entitled to vote thereon. With respect to any such vote, each share of Series A
Preferred Stock shall entitle the holder thereof to cast that number of votes
per share as is equal to the number of votes that such holder would be entitled
to cast had such holder converted its shares of Series A Preferred Stock into
shares of Common Stock on the record date for determining the stockholders of
the Corporation eligible to vote on any such matters.

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              7.     Conversion.

                     (a)    Any holder of Series A Preferred Stock shall have
the right, at its option, at any time and from time to time, to convert, subject
to the terms and provisions of this paragraph 7, any or all of such holder's
shares of Series A Preferred Stock into such number of fully paid and
non-assessable shares of Common Stock as is equal to the product of the number
of shares of Series A Preferred Stock being so converted multiplied by the
quotient of (i) the Liquidation Preference divided by (ii) the conversion price
of $1.8325 per share, subject to adjustment as provided in paragraph 7(d) (the
"Conversion Price"), then in effect. Such conversion right shall be exercised by
the surrender of the shares of Series A Preferred Stock to be converted to the
Corporation at any time during usual business hours at its principal place of
business to be maintained by it, accompanied by written notice that the holder
elects to convert such shares of Series A Preferred Stock and specifying the
name or names (with address) in which a certificate or certificates for shares
of Common Stock are to be issued and (if so required by the Corporation) by a
written instrument or instruments of transfer in form reasonably satisfactory to
the Corporation duly executed by the holder or its duly authorized legal
representative and transfer tax stamps or funds therefor, if required pursuant
to paragraph 7(i). All shares of Series A Preferred Stock surrendered for
conversion shall be delivered to the Corporation for cancellation and canceled
by it and no shares of Series A Preferred Stock shall be issued in lieu thereof.

                     (b)    As promptly as practicable after the surrender, as
herein provided, of any shares of Series A Preferred Stock for conversion
pursuant to paragraph 7(a), the Corporation shall deliver to or upon the written
order of the holder of such shares of Series A Preferred Stock so surrendered a
certificate or certificates representing the number of fully paid and
non-assessable shares of Common Stock into which such shares of Series A
Preferred Stock may be or have been converted in accordance with the provisions
of this paragraph 7. Subject to the following provisions of this paragraph and
of paragraph 7(d), such conversion shall be deemed to have been made immediately
prior to the close of business on the date that such shares of Series A
Preferred Stock shall have been surrendered in satisfactory form for conversion,
and the Person or Persons entitled to receive the shares of Common Stock
deliverable upon conversion of such shares of Series A Preferred Stock shall be
treated for all purposes as having become the record holder or holders of such
shares of Common Stock at such appropriate time, and such conversion shall be at
the Conversion Price in effect at such time; provided, however, that no
surrender shall be effective to constitute the Person or Persons entitled to
receive the shares of Common Stock deliverable upon such conversion as the
record holder or holders of such shares of Common Stock while the share transfer
books of the Corporation shall be closed (but not for any period in excess of
five days), but such surrender shall be effective to constitute the Person or
Persons entitled to receive such shares of Common Stock as the record holder or
holders thereof for all purposes immediately prior to the close of business on
the next succeeding day on which such share transfer books are open, and such
conversion shall be deemed to have been made at, and shall be made at the
Conversion Price in effect at, such time on such next succeeding day.



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                     (c)    To the extent permitted by law, when shares of
Series A Preferred Stock are converted, all dividends declared and unpaid on the
shares of Series A Preferred Stock so converted to the date of conversion shall
be immediately due and payable and must accompany the shares of Common Stock
issued upon such conversion.

                     (d)    The Conversion Price shall be subject to adjustment
as follows:

                            (i)    In the event that the Corporation shall at
              any time or from time to time (w) pay a dividend or make a
              distribution (other than a dividend or distribution paid or made
              to holders of shares of Series A Preferred Stock in the manner
              provided in paragraph 3) on the outstanding shares of Common Stock
              in Capital Stock, (x) subdivide the outstanding shares of Common
              Stock into a larger number of shares, (y) combine the outstanding
              shares of Common Stock into a smaller number of shares or (z)
              issue any shares of its Capital Stock in a reclassification of the
              Common Stock, then, and in each such case, the Conversion Price in
              effect immediately prior to such event shall be adjusted (and any
              other appropriate actions shall be taken by the Corporation) so
              that the holder of any share of Series A Preferred Stock
              thereafter surrendered for conversion shall be entitled to receive
              the number of shares of Common Stock or other securities of the
              Corporation that such holder would have owned or would have been
              entitled to receive upon or by reason of any of the events
              described above, had such share of Series A Preferred Stock been
              converted immediately prior to the occurrence of such event. An
              adjustment made pursuant to this paragraph 7(d)(i) shall become
              effective retroactively (x) in the case of any such dividend or
              distribution, to a date immediately following the close of
              business on the record date for the determination of holders of
              Common Stock entitled to receive such dividend or distribution or
              (y) in the case of any such subdivision, combination or
              reclassification, to the close of business on the day upon which
              such corporate action becomes effective.

                            (ii)   If the Corporation shall at any time or from
              time to time issue or sell any shares of Common Stock or Common
              Stock Equivalents at a price per share (the "Offering Price") that
              is less than the Conversion Price then in effect as of the record
              date or Issue Date referred to in the following sentence, as the
              case may be (the "Relevant Date") (treating the Offering Price per
              share of Common Stock, in the case of the issuance of any Common
              Stock Equivalent, as equal to (x) the sum of the price for such
              Common Stock Equivalent plus any additional consideration payable
              (without regard to any anti-dilution adjustments) upon the
              conversion, exchange or exercise of such Common Stock Equivalent
              divided by (y) the number of shares of Common Stock initially
              underlying such Common Stock Equivalent), other than (1) issuances
              or sales for which an adjustment is made pursuant to another
              paragraph of



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<PAGE>   11
              this Section 7(d) and (2) issuances of Common Stock in connection
              with an Excluded Transaction, then, and in each such case, the
              Conversion Price then in effect shall be adjusted to a price equal
              to such Offering Price. Such adjustment shall be made whenever
              such shares of Common Stock or Common Stock Equivalents are
              issued, and shall become effective retroactively to a date
              immediately following the close of business (x) in the case of an
              issuance to the stockholders of the Corporation, as such, on the
              record date for the determination of stockholders entitled to
              receive such shares of Common Stock or Common Stock Equivalents
              and (y) in all other cases, on the date (the "Issue Date") of such
              issuance; provided, however, that the determination as to whether
              an adjustment is required to be made pursuant to this Section
              7(d)(ii) shall only be made upon the issuance of such shares of
              Common Stock or Common Stock Equivalents, and not upon the
              issuance of the security into which such Common Stock Equivalents
              convert, exchange or may be exercised; and provided further, that
              if the convertibility or exercisability feature of all such Common
              Stock Equivalents expires prior to conversion or exercise thereof,
              then the Conversion Price shall be readjusted (but to no greater
              extent than originally adjusted) to a Conversion Price equal to
              that price which would have existed had the expired Common Stock
              Equivalents never been issued or sold.

                            (iii)  In the case the Corporation, at any time or
              from time to time, shall take any action affecting its Common
              Stock similar to or having an effect similar to any of the actions
              described in paragraphs 7(d)(i) or (ii) (but not including any
              action described in any such paragraph) and the Board of Directors
              in good faith determines that it would be equitable in the
              circumstances to adjust the Conversion Price as a result of such
              action, then, and in each such case, the Conversion Price shall be
              adjusted in such manner and at such time as the Board of Directors
              of the Corporation in good faith determines would be equitable in
              the circumstances (such determination to be evidenced in a
              resolution, a certified copy of which shall be mailed to the
              holders of the shares of Series A Preferred Stock).

                            (iv)   Notwithstanding anything herein to the
              contrary, no adjustment under this paragraph 7(d) need be made to
              the Conversion Price unless such adjustment would require an
              increase or decrease of at least 1% of the Conversion Price then
              in effect. Any lesser adjustment shall be carried forward and
              shall be made at the time of and together with the next subsequent
              adjustment, which, together with any adjustment or adjustments so
              carried forward, shall amount to an increase or decrease of at
              least 1% of such Conversion Price. Any adjustment to the
              Conversion Price carried forward and not theretofore made shall be
              made immediately prior to the conversion of any shares of Series A
              Preferred Stock pursuant hereto.


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<PAGE>   12

                            (e)    If the Corporation shall take a record of the
holders of its Common Stock for the purpose of entitling them to receive a
dividend or other distribution, and shall thereafter and before the distribution
to stockholders thereof legally abandon its plan to pay or deliver such dividend
or distribution, then thereafter no adjustment in the Conversion Price then in
effect shall be required by reason of the taking of such record.

                            (f)    Upon any increase or decrease in the
Conversion Price, then, and in each such case, the Corporation promptly shall
deliver to each registered holder of Series A Preferred Stock at least ten (10)
Business Days prior to effecting any of the foregoing transactions a
certificate, signed by the President or a Vice President and by the Treasurer or
an Assistant Treasurer or the Secretary or an Assistant Secretary of the
Corporation, setting forth in reasonable detail the event requiring the
adjustment and the method by which such adjustment was calculated and specifying
the increased or decreased Conversion Price then in effect following such
adjustment.

                            (g)    In case at any time or from time to time:

                                   (i)    the Corporation shall declare a
       dividend (or any other distribution) on its shares of Common Stock;

                                   (ii)   the Corporation shall authorize the
       granting to the holders of its Common Stock of rights or warrants to
       subscribe for or purchase any shares of stock of any class or of any
       other rights or warrants;

                                   (iii)  there shall be any reorganization or
       reclassification of the Common Stock, or any merger or consolidation to
       which the Corporation is a party and for which approval of any of the
       stockholders of the Corporation is required, or any sale or other
       disposition of all or substantially all of the assets of the Corporation;
       or

                                   (iv)   there shall occur a Liquidation Event;
then the Corporation shall mail to each holder of shares of Series A Preferred
Stock at such holder's address as it appears on the transfer books of the
Corporation, as promptly as possible but in any event at least thirty (30) days
prior to the applicable date hereinafter specified, a notice stating (A) the
date on which a record is to be taken for the purpose of such dividend,
distribution or rights or warrants or, if a record is not to be taken, the date
as of which the holders of Common Stock of record to be entitled to such
dividend, distribution or rights are to be determined, or (B) the date on which
such reclassification, reorganization, merger, consolidation, sale, disposition
or Liquidation Event is expected to become effective. Such notice also shall
specify the date as of which it is expected that holders of Common Stock of
record shall be entitled to exchange their Common Stock for shares of stock or
other securities or property or cash


                                       8

<PAGE>   13

deliverable upon such reclassification, reorganization, merger, consolidation,
sale, exchange, transfer, liquidation, dissolution or winding up.

                            (h)    The Corporation shall at all times reserve
and keep available for issuance upon the conversion of the Series A Preferred
Stock, such number of its authorized but unissued shares of Common Stock as will
from time to time be sufficient to permit the conversion of all outstanding
shares of Series A Preferred Stock, and shall take all action required to
increase the authorized number of shares of Common Stock if at any time there
shall be insufficient authorized but unissued shares of Common Stock to permit
such reservation or to permit the conversion of all outstanding shares of Series
A Preferred Stock.

                            (i)    The issuance or delivery of certificates for
Common Stock upon the conversion of shares of Series A Preferred Stock shall be
made without charge to the converting holder of shares of Series A Preferred
Stock for such certificates or for any tax in respect of the issuance or
delivery of such certificates or the securities represented thereby, and such
certificates shall be issued or delivered in the respective names of, or
(subject to compliance with the applicable provisions of federal and state
securities laws) in such names as may be directed by, the holders of the shares
of Series A Preferred Stock converted; provided, however, that the Corporation
shall not be required to pay any tax which may be payable in respect of any
transfer involved in the issuance and delivery of any such certificate in a name
other than that of the holder of the shares of Series A Preferred Stock
converted, and the Corporation shall not be required to issue or deliver such
certificate unless or until the Person or Persons requesting the issuance or
delivery thereof shall have paid to the Corporation the amount of such tax or
shall have established to the reasonable satisfaction of the Corporation that
such tax has been paid.

              8.     Automatic Conversion. Each share of Series A Preferred
Stock shall automatically be converted into such number of fully paid and
nonassessable shares of Common Stock at the then applicable Conversion Price in
accordance with Section 7 hereof upon the earlier of (i) the Corporation
achieving average volume of at least five million shares per day transacted
through its proprietary OptiMark(TM) securities trading system for the latest
twelve month period and operating profit, as normally recorded on the
Corporation's books and records, over the same twelve month period of at least
$10,000,000 and (ii) automatic conversion of all outstanding shares of the
Corporation's Series B Convertible Participating Preferred Stock, $.01 par value
("Series B Stock"), pursuant to Section 7(ii) of the Certificate of Powers,
Designations, Preferences and Rights of the Series B Stock on file with the
Delaware Secretary of State. In the latter event, the Person(s) entitled to
receive the shares of Common Stock issuable upon such conversion of the Series A
Preferred Stock shall not be deemed to have converted the Series A Preferred
Stock until immediately after the closing of the Corporation's initial public
offering, except that any such Person may convert its shares of Series A
Preferred Stock at an earlier time in accordance with Section 7.

                                       9

<PAGE>   14

              9.     Certain Remedies. Any registered holder of Series A
Preferred Stock shall be entitled to an injunction or injunctions to prevent
breaches of the provisions of this Certificate of Designations and to enforce
specifically the terms and provisions of this Certificate of Designations in any
court of the United States or any state thereof having jurisdiction, this being
in addition to any other remedy to which such holder may be entitled at law or
in equity.

              10.    Reissuance of Series A Preferred Stock. Shares of Series A
Preferred Stock that have been issued and reacquired in any manner, including
shares purchased or converted, shall (upon compliance with any applicable
provisions of the laws of Delaware) have the status of authorized and unissued
shares of Preferred Stock undesignated as to series and may be redesignated and
reissued as part of any series of preferred stock (other than Series A Preferred
Stock).

              11.    Business Day. If any payment shall be required by the terms
hereof to be made on a day that is not a Business Day, such payment shall be
made on the immediately succeeding Business Day.

              12.    Definitions. As used in this Certificate of Designations,
the following terms shall have the following meanings (with terms defined in the
singular having comparable meanings when used in the plural and vice versa),
unless the context otherwise requires:

              "Board of Directors" means the Board of Directors of the
Corporation.

              "Business Day" means any day except a Saturday, a Sunday, or other
day on which commercial banks in the State of New York are authorized or
required by law or executive order to close.

              "Capital Stock" means, with respect to any Person, any and all
shares, interests, participations, rights in, or other equivalents (however
designated and whether voting or non-voting) of, such Person's capital stock and
any and all rights, warrants or options exchangeable for or convertible into
such capital stock (but, solely for the purposes of paragraph 2, excluding any
debt security that is exchangeable for or convertible into such capital stock).

              "Commission" means the Securities and Exchange Commission or any
similar agency then having jurisdiction to enforce the Securities Act.

              "Common Stock" shall have the meaning ascribed to it in paragraph
2 hereof.

              "Common Stock Equivalents" means any security or obligation which
is by its terms convertible into or exchangeable for shares of Common Stock,
including, without limitation, the Series A Preferred Stock, and any option,
warrant or other subscription or purchase right with respect to shares of Common
Stock.



                                       10
<PAGE>   15


              "Exchange Act" means the Securities Exchange Act of 1934, and the
rules and regulations of the Commission promulgated thereunder.

              "Excluded Transaction" shall mean (i) the issuance of up to
6,534,268 shares of Common Stock pursuant to options, warrants and compensatory
stock grants, issued and reserved for issuance as incentives for the
Corporation's officers, directors, employees, former employees and consultants,
(ii) the issuance pursuant to a warrant in favor of The Pacific Exchange,
Incorporated dated August 27, 1996, of up to 2,104,000 shares of Common Stock
(subject to adjustment as provided therein), (iii) the issuance pursuant to a
warrant in favor of The Chicago Board Options Exchange, Incorporated dated
December 31, 1996, of up to 1,000,000 shares of Common Stock (subject to
adjustment as provided therein), (iv) the issuance pursuant to a warrant in
favor of Dow Jones & Company, Inc. dated May 29, 1997, of up to 2,161,764 shares
of Common Stock (subject to adjustment as provided therein), (v) the issuance
pursuant to a warrant in favor of The Nasdaq Stock Market, Inc. dated September
1, 1998, of up to 11,250,000 shares of Common Stock (subject to adjustment as
provided therein), (vi) the issuance of Common Stock upon conversion of the
Series A Stock, and (vii) the issuance pursuant to a warrant in favor of
Virginia Surety Company, Inc. dated April 23, 1998, of up to 500,000 shares of
Common Stock (subject to adjustment as provided therein).

              "Fair Market Value" shall mean the amount which a willing buyer
would pay a willing seller in an arm's length transaction.

              "Person" means any individual, firm, corporation, partnership,
limited liability company, trust, incorporated or unincorporated association,
joint venture, joint stock company, governmental body or other entity of any
kind.

              "Securities Act" means the Securities Act of 1933, as amended, and
the rules and regulations of the Commission promulgated thereunder.


                                       11

<PAGE>   16




              IN WITNESS WHEREOF, the Corporation has caused this certificate to
be duly executed by its Chief Executive Officer this 9th day of June, 2000

                                          OPTIMARK HOLDINGS, INC.

                                          By:  /s/ Phillip J. Riese
                                             -------------------------------
                                                   Chief Executive Officer




                                       12
<PAGE>   17



                      CERTIFICATE OF POWERS, DESIGNATIONS,

                          PREFERENCES AND RIGHTS OF THE

               SERIES B CONVERTIBLE PARTICIPATING PREFERRED STOCK,

                            PAR VALUE $.01 PER SHARE

             Pursuant to Section 151 of the General Corporation Law
                            of the State of Delaware

The following resolution was duly adopted by the Board of Directors of OptiMark
Holdings, Inc., a Delaware corporation (the "Corporation"), pursuant to the
provisions of Section 151 of the General Corporation Law of the State of
Delaware, effective as of June 9, 2000, by unanimous written consent of the
Board of Directors.

              WHEREAS, the Board of Directors is authorized, within the
limitations and restrictions stated in the Restated Certificate of Incorporation
of the Corporation, to provide by resolution or resolutions for the issuance of
shares of Preferred Stock, par value $.01 per share, of the Corporation, in one
or more series with such voting powers, full or limited, or without voting
powers, and such designations, preferences and relative, participating, optional
or other special rights, and qualifications, limitations or restrictions as
shall be stated and expressed in the resolution or resolutions providing for the
issuance thereof adopted by the Board of Directors, and as are not stated and
expressed in the Certificate of Incorporation, or any amendment thereto,
including (but without limiting the generality of the foregoing) such provisions
as may be desired concerning voting, redemption, dividends, dissolution or the
distribution of assets and such other subjects or matters as may be fixed by
resolution or resolutions of the Board of Directors under the General
Corporation Law of the State of Delaware; and

              WHEREAS, it is the desire of the Board of Directors, pursuant to
its authority as aforesaid, to authorize and fix the terms of a series of
preferred stock and the number of shares constituting such series.

              NOW THEREFORE, BE IT RESOLVED:

              1.     Designation and Number of Shares. There is hereby
established a series of Preferred Stock of the Corporation designated as "Series
B Convertible Participating Preferred Stock" (the "Series B Stock"). The
authorized number of shares of Series B Stock shall be eleven million
(11,000,000).

              2.     Dividends.
<PAGE>   18

              (a) If the Board of Directors of the Corporation shall declare a
dividend or make any other distribution (including, without limitation, in cash,
evidences of indebtedness of the Corporation or another issuer, securities of
the Corporation or another issuer, or other property or assets), to holders of
shares of Common Stock, then the holder of each share of Series B Stock
theretofore issued shall be entitled to receive, out of funds legally available
therefor, a dividend or distribution in an amount equal to the amount of such
dividend or distribution received by a holder of the number of shares of Common
Stock for which such share of Series B Stock is convertible on the record date
for such dividend or distribution. Any such amount shall be paid to the holders
of shares of Series B Stock at the same time such dividend or distribution is
made to holders of Common Stock.

              (b) Except as otherwise provided in paragraph (a) above, the
Series B Stock shall not be entitled to any dividends.

              3.     Liquidation Preference.

              (a) In connection with any Liquidation of the Corporation, (i) if
the assets of the Corporation available for distribution to the stockholders are
sufficient both to pay the Series A Liquidation Amount with respect to each
outstanding share of Series A Stock and to pay the Series B Liquidation Amount
with respect to each outstanding share of Series B Stock, then the holders of
Series B Stock then outstanding shall be entitled to be paid the Series B
Liquidation Amount for each share of Series B Stock held thereby, (ii) if the
assets of the Corporation available for distribution to the stockholders are not
sufficient so to pay both the Series A Liquidation Amount and the Series B
Liquidation Amount, then the holders of the outstanding shares of Series A Stock
and Series B Stock shall share pari passu in the distribution of available
assets, pro rata to the amounts that would have been payable to such holders if
the assets of the Corporation available for distribution to the stockholders in
Liquidation had been sufficient to pay both the Series A Liquidation Amount and
the Series B Liquidation Amount in full, and (iii) the Series B Liquidation
Amount must be paid in full with respect to each outstanding share of Series B
Stock before any payment shall be made or any assets distributed to the holders
of any shares of Common Stock or any other securities which, by their terms,
have expressly been made junior to the Series B Stock in Liquidation.

              (b) Written notice of any Liquidation, stating a payment date, the
amount of the payment determined pursuant to this paragraph 3 and the place
where such amount shall be payable, shall be delivered in person, mailed by
certified or registered mail, return receipt requested, mailed by overnight mail
or sent by telecopier, not less than ten (10) days prior to the payment date
stated therein, to the holders of record of the Series B Stock, such notice to
be addressed to each such holder at its address as shown by the records of the
Corporation.

              (c) The fair value of the assets to be distributed or exchanged
(to the extent that distributions are not made in cash) in the event of
Liquidation shall be



                                       2

<PAGE>   19

determined as provided in the Certificate of Designations on file with the
Delaware Secretary of State with respect to the Series A Stock (the "Series A
Certificate").

              (d) For purposes of this Certificate of Designations, (i)
"Liquidation" means any voluntary or involuntary liquidation, dissolution or
winding-up of the Corporation, under the U.S. Bankruptcy Code or otherwise, (ii)
"Series A Stock" means the Corporation's Series A Convertible Participating
Preferred Stock, $.01 par value, (iii) the "Series A Liquidation Amount" means
the amount payable upon Liquidation to the holders of the Series A Stock, as
provided in the Series A Certificate, and (iv) the "Series B Liquidation Amount"
means Ten Dollars ($10.00) per share of Series B Stock plus all declared and
unpaid dividends thereon (if any) through the effective date of Liquidation.

              4.     Redemption. The shares of Series B Stock shall not be
redeemable at the option of the Corporation or at the option of any holder
thereof.

              5.     Voting Rights; Election of Directors. Each issued and
outstanding share of Series B Stock shall entitle the holder thereof to vote, in
person or by proxy, at each special and annual meeting of stockholders of the
Corporation, on all matters entitled to be voted on by holders of voting Common
Stock. To the maximum extent permitted by law, on all matters submitted to a
vote of the stockholders, the holders of the Series B Stock shall vote as a
single class together with the holders of voting Common Stock and with all other
shares (including the outstanding shares of Series A Stock) entitled to vote
with the voting Common Stock thereon. With respect to any such vote, each share
of Series B Stock shall entitle the holder thereof to cast that number of votes
per share as is equal to the number of votes that such holder would be entitled
to cast had such holder converted its shares of Series B Stock into shares of
Common Stock on the record date for determining the stockholders of the
Corporation eligible to vote on such matters.

              6.     Conversion.

              (a) Any holder of Series B Stock shall have the right, at its
option, at any time and from time to time, to convert, subject to the terms and
provisions of this paragraph 6, any or all of such holder's shares of Series B
Stock into such number of fully paid and nonassessable shares of voting Common
Stock as is equal to the product of the number of shares of Series B Stock being
so converted multiplied by the quotient of (i) the Liquidation Amount, divided
by (ii) the conversion price of $10.00 per share, subject to adjustment as
provided in paragraph 6(c) (the "Conversion Price"), then in effect. Such
conversion right shall be exercised by the surrender of the shares of Series B
Stock to be converted to the Corporation at any time during usual business hours
at its principal place of business to be maintained by it, accompanied by
written notice that the holder elects to convert such shares of Series B Stock
and specifying the name or names (with address) in which a certificate or
certificates for shares of voting Common Stock are to be issued and (if so
required by the Corporation) by a written instrument or instruments of transfer
in form reasonably satisfactory to the Corporation duly executed


                                       3

<PAGE>   20

by the holder or its duly authorized legal representative and transfer tax
stamps or funds therefor, if required pursuant to paragraph 6(h).

              (b) As promptly as practicable after the surrender, as herein
provided, of any shares of Series B Stock for conversion pursuant to paragraph
6(a), the Corporation shall deliver to or per the written order of the holder of
such shares of Series B Stock so surrendered a certificate or certificates
representing the number of fully paid and nonassessable shares of voting Common
Stock into which such shares of Series B Stock may be or have been converted in
accordance with the provisions of this paragraph 6. Subject to the following
provisions of this paragraph and of paragraph 6(c), such conversion shall be
deemed to have been made immediately prior to the close of business on the date
that such shares of Series B Stock shall have been surrendered in satisfactory
form for conversion, and the Person or Persons entitled to receive the shares of
Common Stock deliverable upon conversion of such shares of Series B Stock shall
be treated for all purposes as having become the record holder or holders of
such shares of Common Stock at such appropriate time, and such conversion shall
be at the Conversion Price in effect at such time; provided, however, that no
surrender shall be effective to constitute the Person or Persons entitled to
receive the shares of Common Stock deliverable upon such conversion as the
record holder or holders of such shares of Common Stock while the share transfer
books of the Corporation shall be closed (but not for any period in excess of
five days), but such surrender shall be effective to constitute the Person or
Persons entitled to receive such shares of Common Stock as the record holder or
holders thereof for all purposes immediately prior to the close of business on
the next succeeding day on which such share transfer books are open, and such
conversion shall be deemed to have been made at, and shall be made at the
Conversion Price in effect at, such time on such next succeeding day.

              (c) The Conversion Price shall also be subject to adjustment as
follows:

                     (i)    In the event that the Corporation shall at any time
or from time to time (w) pay a dividend or make a distribution (other than a
dividend or distribution paid or made to holders of shares of Series B Stock in
the manner provided in paragraph 2) on the outstanding shares of Common Stock in
Capital Stock, (x) subdivide the outstanding shares of Common Stock into a
larger number of shares, (y) combine the outstanding shares of Common Stock into
a smaller number of shares or (z) issue any shares of its Capital Stock in a
reclassification of the Common Stock, then, and in each such case, the
Conversion Price in effect immediately prior to such event shall be adjusted
(and any other appropriate actions shall be taken by the Corporation) so that
the holder of any share of Series B Stock thereafter surrendered for conversion
shall be entitled to receive the number of shares of voting Common Stock or
other securities of the Corporation that such holder would have owned or to
which such holder would have been entitled to receive upon or by reason of any
of the events described above, had such share of Series B Stock been converted
into Common Stock immediately prior to the occurrence of such event. An
adjustment made pursuant to this paragraph 6(c)(i) shall become effective
retroactively (x) in the case of any such dividend or distribution, to a date
immediately following the close of business on the record date for the
determination


                                       4

<PAGE>   21

of holders of Common Stock entitled to receive such dividend or distribution, or
(y) in the case of any such subdivision, combination or reclassification, to the
close of business on the day upon which such corporate action becomes effective.

              (ii) If the Corporation shall at any time or from time to time
issue or sell any shares of Common Stock or Common Stock Equivalents at a price
per share (the "Offering Price") that is less than the Conversion Price then in
effect as of the record date or Issue Date referred to in the following
sentence, as the case may be (the "Relevant Date") (treating the Offering Price
per share of Common Stock, in the case of the issuance of any Common Stock
Equivalent, as equal to (x) the sum of the price for such Common Stock
Equivalent plus any additional consideration payable (without regard to any
anti-dilution adjustments) upon the conversion, exchange or exercise of such
Common Stock Equivalent, divided by (y) the number of shares of Common Stock
initially underlying such Common Stock Equivalent), other than (1) issuances or
sales for which an adjustment is made pursuant to another paragraph of this
Section 6(c) and (2) issuances of Common Stock in connection with an Excluded
Transaction, then, and in each such case, the Conversion Price then in effect
shall be reduced, concurrently with such issuance, to a price determined by
multiplying such Conversion Price by a fraction, the numerator of which shall be
the number of shares of Common Stock outstanding immediately prior to such
issuance plus the number of shares of Common Stock that the aggregate
consideration received by the Corporation for the total number of additional
shares of Common Stock or Common Stock Equivalents so issued would purchase at
such Conversion Price; and the denominator of which shall be the number of
shares of Common Stock outstanding immediately prior to such issuance plus the
number of such additional shares of Common Stock or Common Stock Equivalents so
issued. Such adjustment shall be made whenever such shares of Common Stock or
Common Stock Equivalents are issued, and shall become effective retroactively to
a date immediately following the close of business (x) in the case of an
issuance to the stockholders of the Corporation, as such, on the record date for
the determination of stockholders entitled to receive such shares of Common
Stock or Common stock Equivalents and (y) in all other cases, on the date (the
"Issue Date") of such issuance; provided, however, that the determination as to
whether an adjustment is required to be made pursuant to this Section 6(c)(ii)
shall only be made upon the issuance of such shares of Common Stock or Common
Stock Equivalents, and not upon the issuance of the security into which such
Common Stock Equivalents convert, exchange or may be exercised; and provided
further, that if and to the extent that the convertibility or exercisability
feature of such Common Stock Equivalents expires prior to conversion or exercise
thereof, then the Conversion Price shall be readjusted (but to no greater extent
than originally adjusted) to a Conversion Price equal to that price which would
have existed had the expired Common Stock Equivalents never been issued or sold.

              (iii) In the case the Corporation, at any time or from time to
time, shall take any action affecting its Common Stock similar to or having an
effect similar to any of the actions described in paragraphs 6(c)(i) or (ii)
(but not including any action described in any such paragraphs) and the Board of
Directors in good faith determines that it would be equitable in the
circumstances to adjust the Conversion Price


                                       5

<PAGE>   22

as a result of such action, then, and in each such case, the Conversion Price
shall be adjusted in such manner and at such time as the Board of Directors of
the Corporation in good faith determines would be equitable in the circumstances
(such determination to be evidenced in a resolution, a certified copy of which
shall be mailed to the holders of the shares of Series B Stock).

              (d) If the Corporation shall take a record of the holders of its
Common Stock for the purpose of entitling them to receive a dividend or other
distribution, and shall thereafter and before the distribution to stockholders
thereof legally abandon its plan to pay or deliver such dividend or
distribution, then thereafter no adjustment in the Conversion Price then in
effect shall be required by reason of the taking of such record.

              (e) Upon any increase or decrease in the Conversion Price, then,
and in each such case, the Corporation promptly shall deliver to each registered
holder of Series B Stock at least ten (10) Business Days prior to effecting any
of the foregoing transactions a certificate, signed by the President or a Vice
President and by the Treasurer, an Assistant Treasurer, the Secretary or an
Assistant Secretary of the Corporation, setting forth in reasonable detail the
event requiring the adjustment and the method by which such adjustment was
calculated and specifying the increased or decreased Conversion Price then in
effect following such adjustment.

              (f) In case at any time or from time to time:

                     (i)    The Corporation shall declare a dividend (or any
other distribution) on its shares of Capital Stock;

                     (ii)   the Corporation shall authorize the granting to the
holders of its Capital Stock of rights or warrants to subscribe for or purchase
any shares of stock of any class or of any other rights or warrants;

                     (iii)  there shall be any reorganization or
reclassification of the Capital Stock of the Corporation, or any merger or
consolidation to which the Corporation is a party and for which approval of any
of the stockholders of the Corporation is required, or any sale or other
disposition of all or substantially all of the assets of the Corporation; or

                     (iv)   there shall occur a Liquidation;

then the Corporation shall mail to each holder of shares of Series B Stock at
such holder's address as it appears on the transfer books of the Corporation, as
promptly as possible but in any event at least thirty (30) days prior to the
applicable date hereinafter specified, a notice stating (A) the date on which a
record is to be taken for the purpose of such dividend, distribution, rights or
warrants or, if a record is not to be taken, the date as of which the holders of
Common Stock of record to be entitled to such dividend, distribution or rights
are to be determined, or (B) the date on which such reclassification,
reorganization, merger, consolidation, sale, disposition or Liquidation is
expected to

                                       6
<PAGE>   23


become effective. Such notice also shall specify the date as of which it is
expected that holders of Common Stock of record shall be entitled to exchange
their Common Stock for shares of stock or other securities or property or cash
deliverable upon such reclassification, reorganization, merger, consolidation,
sale, exchange, transfer or Liquidation.

              (g)    The Corporation shall at all times reserve and keep
available for issuance upon the conversion of the Series B Stock, such number of
its authorized but unissued shares of voting Common Stock as will from time to
time be sufficient to permit the conversion of all outstanding shares of Series
B Stock, and shall take all action required to increase the authorized number of
shares of voting Common Stock if at any time there shall be insufficient
authorized but unissued shares of Common Stock to permit such reservation or to
permit the conversion of all outstanding shares of Series B Stock.

              (h)    The issuance or delivery of certificates for Common Stock
upon the conversion of shares of Series B Stock shall be made without charge to
the converting holder of shares of Series B Stock for such certificates or for
any tax in respect of the issuance or delivery of such certificates or the
securities represented thereby, and such certificates shall be issued or
delivered in the respective names of, or (subject to compliance with the
applicable provisions of federal and state securities laws) in such names as may
be directed by, the holders of the shares of Series B Stock converted; provided,
however, that the Corporation shall not be required to pay any tax which may be
payable in respect of any transfer involved in the issuance and delivery of any
such certificate in a name other than that of the holder of the shares of Series
B Stock converted, and the Corporation shall not be required to issue or deliver
such certificate unless or until the Person requesting the issuance or delivery
thereof shall have paid to the Corporation the amount of such tax or shall have
established to the reasonable satisfaction of the Corporation that such tax has
been paid.

              7.     Automatic Conversion. Each share of Series B Stock shall
automatically be converted into such number of fully paid and nonassessable
shares of voting Common Stock at the then applicable Conversion Price in
accordance with Section 6 hereof upon the earlier of (i) the Corporation
achieving average volume of at least five million (5,000,000) shares per day
transacted through its proprietary OptiMark(TM) trading system for the latest
twelve month period and operating profit, as normally recorded on the
Corporation's books and records, over the same twelve month period of at least
$10,000,000, or (ii) immediately after the closing of an underwritten initial
public offering ("IPO") pursuant to an effective registration statement filed
under the Securities Act covering the offer and sale of shares of Common Stock
for the account of the Corporation at a price per share of Common Stock that is
not less that twice (200% of) the then applicable Conversion Price and resulting
in aggregate gross proceeds to the Corporation of at least $10,000,000. In the
event of an IPO, the Person(s) entitled to receive the shares of Common Stock
issuable upon such conversion of the Series B Stock shall not be deemed to have
converted the Series B Stock until immediately after the


                                       7

<PAGE>   24

closing of such offering, except that any such Person may convert its shares of
Series B Stock at any earlier time in accordance with paragraph 6.

              8.     Certain Remedies. Any registered holder of Series B Stock
shall be entitled to an injunction or injunctions to prevent breaches of the
provisions of this Certificate of Designations and to enforce specifically the
terms and provisions of this Certificate of Designations in any court of the
United States or any state thereof having jurisdiction, this being in addition
to any other remedy to which such holder may be entitled at law or in equity.

              9.     Reissuance of Series B Stock. Shares of Series B Stock that
have been issued and reacquired in any manner, including shares redeemed or
converted, shall (upon compliance with any applicable provisions of the laws of
Delaware) have the status of authorized and unissued shares of Preferred Stock
of the Corporation, undesignated as to series, and may be redesignated and
reissued as part of any series of preferred stock (including Series B Stock).

              10.    Amendment. This Certificate of Designations may be amended
with (and only with) the written consent of (i) the Corporation, and (ii) the
holders of not less than 75% of the outstanding shares of Series B Stock.

              11.    Definitions. As used in this Certificate of Designation, in
addition to other capitalized terms defined elsewhere in this Certificate, the
following terms shall have the following meanings (with terms defined in the
singular having comparable meanings when used in the plural and vice versa),
unless the context otherwise requires:

              "Board of Directors" means the Board of Directors of the
Corporation.

              "Capital Stock" means, with respect to any Person, any and all
shares, interests, participations, rights in, or other equivalents (however
designated and whether voting or nonvoting) of such Person's capital stock and
any and all rights, warrants or options exchangeable for or convertible into
such capital stock.

              "Commission" means the Securities and Exchange Commission or any
similar agency then having jurisdiction to enforce the Securities Act.

              "Common Stock" means the Corporation's common stock (including
both voting and nonvoting common stock), $.01 par value per share.

              "Common Stock Equivalents" means any security or obligation which
is by its terms convertible into or exchangeable for shares of Common Stock,
including, without limitation, the Series A Stock, the Series B Stock, and any
option, warrant or other subscription or purchase right with respect to shares
of Common Stock.

              "Exchange Act" means the Securities Exchange Act of 1934, and the
rules and regulations of the Commission promulgated thereunder.


                                       8
<PAGE>   25


              "Excluded Transaction" shall mean (i) the issuance of up to
6,534,268 shares of Common Stock pursuant to options, warrants and compensatory
stock grants, issued and reserved for issuance as incentives for the
Corporation's officers, directors, employees, former employees and consultants,
(ii) the issuance pursuant to a warrant in favor of The Pacific Exchange,
Incorporated dated August 27, 1996, of up to 2,104,000 shares of Common Stock
(subject to adjustment as provided therein), (iii) the issuance pursuant to a
warrant in favor of The Chicago Board Options Exchange, Incorporated dated
December 31, 1996 of up to 1,000,000 shares of Common Stock (subject to
adjustment as provided therein), (iv) the issuance pursuant to a warrant in
favor of Dow Jones & Company, Inc. dated May 29, 1997, of up to 2,161,764 shares
of Common Stock (subject to adjustment as provided therein), (v) the issuance
pursuant to a warrant in favor of The Nasdaq Stock Market, Inc. dated September
1, 1998, of up to 11,250,000 shares of Common Stock (subject to adjustment as
provided therein), (vi) the issuance of Common Stock upon conversion of the
Series A Stock, and (vii) the issuance pursuant to a warrant in favor of
Virginia Surety Company, Inc. dated April 23, 1998, of up to 500,000 shares of
Common Stock (subject to adjustment as provided therein).

              "Fair Market Value" shall mean the amount which a willing buyer
would pay a willing seller in an arm's length transaction.

              "Person" means any individual, firm, corporation, partnership,
limited liability company, trust, incorporated or unincorporated association,
joint venture, joint stock company, governmental body or other entity of any
kind.

              "Securities Act" means the Securities Act of 1933, as amended, and
the rules and regulations of the Commission promulgated thereunder.

              "Shares outstanding" or "Shares then outstanding" means all shares
of Common Stock outstanding and all shares of Common Stock issuable upon
conversion, exercise or exchange of any option, warrant or other security or
obligation which is, by its terms, convertible, exercisable or exchangeable into
shares of Common Stock, whether or not such conversion, exercise or exchange has
actually been effected.



                                       9

<PAGE>   26




              IN WITNESS WHEREOF, the Corporation has caused this certificate to
be duly executed by its Chief Executive Officer this 9th day of June, 2000



                                          OPTIMARK HOLDINGS, INC.

                                          By:  /s/ Phillip J. Riese
                                                   Chief Executive Officer



                                       10
<PAGE>   27


                      CERTIFICATE OF POWERS, DESIGNATIONS,

                          PREFERENCES AND RIGHTS OF THE

                      SERIES C CONVERTIBLE PREFERRED STOCK,

                            PAR VALUE $.01 PER SHARE
             Pursuant to Section 151 of the General Corporation Law
                            of the State of Delaware

       The following resolution was duly adopted by the Board of Directors of
OptiMark Holdings, Inc., a Delaware corporation (the "Corporation"), pursuant to
the provisions of Section 151 of the General Corporation Law of the State of
Delaware, effective as of June 9, 2000, by unanimous written consent of the
Board of Directors.

       WHEREAS, the Board of Directors is authorized, within the limitations and
restrictions stated in the Certificate of Incorporation of the Corporation, (the
"Certificate of Incorporation") to provide by resolution or resolutions for the
issuance of shares of Preferred Stock, par value $.01 per share, of the
Corporation, in one or more classes or series with such voting powers, full or
limited, or without voting powers, and such designations, preferences and
relative, participating, optional or other special rights, and qualifications,
limitations or restrictions as shall be stated and expressed in the resolution
or resolutions providing for the issuance thereof adopted by the Board of
Directors, and as are not stated and expressed in the Certificate of
Incorporation, or any amendment thereto, including (but without limiting the
generality of the foregoing) such provisions as may be desired concerning
voting, redemption, dividends, dissolution or the distribution of assets and
such other subjects or matters as may be fixed by resolution or resolutions of
the Board of Directors under the General Corporation Law of the State of
Delaware; and

       WHEREAS, it is the desire of the Board of Directors, pursuant to its
authority as aforesaid, to authorize and fix the terms of a series of preferred
stock and the number of shares constituting such series.

       NOW THEREFORE, BE IT RESOLVED:

       1.     Designation and Number of Shares. There is hereby established a
series of Preferred Stock of the Corporation designated as "Series C Convertible
Preferred Stock" (the "Series C Stock"). The authorized number of shares of
Series C Stock shall be eight million two hundred fifty thousand (8,250,000).




       2.     Dividends.


<PAGE>   28

              (a)    If the Board of Directors of the Corporation shall declare
a dividend or make any other distribution (including, without limitation, in
cash, evidences of indebtedness of the Corporation or another issuer, securities
of the Corporation other than Common Stock or another issuer, or other property
or assets), to holders of shares of Common Stock, then the holder of each share
of Series C Stock theretofore issued shall be entitled to receive, out of funds
legally available therefor, a dividend or distribution in an amount equal to the
amount of such dividend or distribution received by a holder of the number of
shares of Common Stock for which such share of Series C Stock is convertible on
the record date for such dividend or distribution. Any such amount shall be paid
to the holders of shares of Series C Stock at the same time such dividend or
distribution is made to holders of Common Stock.

              (b)    Except as otherwise provided in paragraph (a) above, the
Series C Stock shall not be entitled to any dividends.

       3.     Liquidation Preference.

              (a)    In connection with any Liquidation of the Corporation, (i)
if the assets of the Corporation available for distribution to the stockholders
are sufficient to pay the Series A Liquidation Amount with respect to each
outstanding share of Series A Stock, to pay the Series B Liquidation Amount with
respect to each outstanding share of Series B Stock and to pay the Series C
Liquidation Amount with respect to each outstanding share of Series C Stock,
then the holders of Series C Stock then outstanding shall be entitled to be paid
the Series C Liquidation Amount for each share of Series C Stock held thereby
before any payment shall be made or any assets distributed to the holders of any
shares of Junior Stock (as hereinafter defined), (ii) if the assets of the
Corporation available for distribution to the stockholders are not sufficient to
pay the Series A Liquidation Amount, the Series B Liquidation Amount and the
Series C Liquidation Amount, then the holders of the outstanding shares of
Series A Stock, Series B Stock and Series C Stock shall share pari passu in the
distribution of available assets, pro rata to the amounts that would have been
payable to such holders if the assets of the Corporation available for
distribution to the stockholders in Liquidation had been sufficient to pay the
Series A Liquidation Amount, the Series B Liquidation Amount and the Series C
Liquidation Amount in full, and (iii) the Series C Liquidation Amount must be
paid in full with respect to each outstanding share of Series C Stock before any
payment shall be made or any assets distributed to the holders of any shares of
Common Stock or any other securities which, by their terms, have expressly been
made junior to the Series C Stock in Liquidation (the "Junior Stock").

              (b)    Written notice of any Liquidation, stating a payment date,
the amount of the payment determined pursuant to this paragraph 3 and the place
where such amount shall be payable, shall be delivered in person, mailed by
certified or registered mail, return receipt requested, mailed by overnight mail
or sent by telecopier, not less than ten (10) days prior to the payment date
stated therein, to the holders of record of the Series C Stock, such notice to
be addressed to each such holder at its address as shown by the records of the
Corporation.


              (c)    The fair value of the assets to be distributed or exchanged
(to the extent that distributions are not made in cash) in the event of
Liquidation shall be determined as provided in the




                                     - 2 -
<PAGE>   29

Certificate of Designations on file with the Delaware Secretary of State with
respect to the Series A Stock (the "Series A Certificate").

              (d)    For purposes of this Certificate of Designations, (i)
"Liquidation" means any voluntary or involuntary liquidation, dissolution or
winding-up of the Corporation, under the U.S. Bankruptcy Code or otherwise, (ii)
"Series A Stock" means the Corporation's Series A Convertible Participating
Preferred Stock, $.01 par value, (iii) the "Series A Liquidation Amount" means
the amount payable upon Liquidation to the holders of the Series A Stock, as
provided in the Series A Certificate, (iv) "Series B Stock" means the
Corporation's Series B Convertible Participating Preferred Stock, $.01 par
value, (v) the "Series B Liquidation Amount" means the amount payable upon
Liquidation to the holders of the Series B Stock, as provided in the Certificate
of Designations on file with the Delaware Secretary of State with respect to the
Series B Stock and (vi) the "Series C Liquidation Amount" means $11.75758 per
share of Series C Stock plus all declared and unpaid dividends thereon (if any)
through the effective date of Liquidation.

       4.     Redemption. The shares of Series C Stock shall not be redeemable
at the option of the Corporation or at the option of any holder thereof.

       5.     Voting Rights; Election of Directors. Each issued and outstanding
share of Series C Stock shall entitle the holder thereof to vote, in person or
by proxy, at each special and annual meeting of stockholders of the Corporation,
on all matters entitled to be voted on by holders of voting Common Stock. To the
maximum extent permitted by law, on all matters submitted to a vote of the
stockholders, the holders of the Series C Stock shall vote as a single class
together with the holders of voting Common Stock and with all other shares
(including the outstanding shares of Series A Stock and Series B Stock) entitled
to vote with the voting Common Stock thereon. With respect to any such vote,
each share of Series C Stock shall entitle the holder thereof to cast that
number of votes per share as is equal to the number of votes that such holder
would be entitled to cast had such holder converted its shares of Series C Stock
into shares of Common Stock on the record date for determining the stockholders
of the Corporation eligible to vote on such matters.

       6.     Conversion.

              (a)    Any holder of Series C Stock shall have the right, at its
option, at any time and from time to time, to convert, subject to the terms and
provisions of this paragraph 6, any or all of such holder's shares of Series C
Stock into such number of fully paid and nonassessable shares of voting Common
Stock as is equal to the product of the number of shares of Series C Stock being
so converted multiplied by the quotient of (i) the Liquidation Amount, divided
by (ii) the conversion price of $11.75758 per share, subject to adjustment as
provided in paragraph 6(c) (the "Conversion Price"), then in effect. Such
conversion right shall be exercised by the surrender of the shares of Series C
Stock to be converted to the Corporation at any time during usual business hours
at its principal place of business to be maintained by it, accompanied by
written notice that the holder elects to convert such shares of Series C Stock
and specifying the name or names (with address) in which a certificate or
certificates for shares of voting Common Stock are to be issued and (if so
required by the Corporation) by a written instrument or instruments of transfer
in form reasonably



                                     - 3 -
<PAGE>   30

satisfactory to the Corporation duly executed by the holder or its duly
authorized legal representative and transfer tax stamps or funds therefor, if
required pursuant to paragraph 6(h).

              (b)    As promptly as practicable after the surrender, as herein
provided, of any shares of Series C Stock for conversion pursuant to paragraph
6(a), the Corporation shall deliver to or per the written order of the holder of
such shares of Series C Stock so surrendered a certificate or certificates
representing the number of fully paid and nonassessable shares of voting Common
Stock into which such shares of Series C Stock may be or have been converted in
accordance with the provisions of this paragraph 6. Subject to the following
provisions of this paragraph and of paragraph 6(c), such conversion shall be
deemed to have been made immediately prior to the close of business on the date
that such shares of Series C Stock shall have been surrendered in satisfactory
form for conversion, and the Person or Persons entitled to receive the shares of
voting Common Stock deliverable upon conversion of such shares of Series C Stock
shall be treated for all purposes as having become the record holder or holders
of such shares of voting Common Stock at such appropriate time, and such
conversion shall be at the Conversion Price in effect at such time; provided,
however, that no surrender shall be effective to constitute the Person or
Persons entitled to receive the shares of voting Common Stock deliverable upon
such conversion as the record holder or holders of such shares of voting Common
Stock while the share transfer books of the Corporation shall be closed (but not
for any period in excess of five days), but such surrender shall be effective to
constitute the Person or Persons entitled to receive such shares of voting
Common Stock as the record holder or holders thereof for all purposes
immediately prior to the close of business on the next succeeding day on which
such share transfer books are open, and such conversion shall be deemed to have
been made at, and shall be made at the Conversion Price in effect at, such time
on such next succeeding day.

              (c)    The Conversion Price shall be subject to adjustment as
follows:

                     (i)    In the event that the Corporation shall at any time
or from time to time (w) pay a dividend or make a distribution (other than a
dividend or distribution paid or made to holders of shares of Series C Stock in
the manner provided in paragraph 2) on the outstanding shares of Common Stock in
Capital Stock, (x) subdivide the outstanding shares of Common Stock into a
larger number of shares, (y) combine the outstanding shares of Common Stock into
a smaller number of shares or (z) issue any shares of its Capital Stock in a
reclassification of the Common Stock, then, and in each such case, the
Conversion Price in effect immediately prior to such event shall be adjusted
(and any other appropriate actions shall be taken by the Corporation) so that
the holder of any share of Series C Stock thereafter surrendered for conversion
shall be entitled to receive the number of shares of voting Common Stock or
other securities of the Corporation that such holder would have owned or to
which such holder would have been entitled to receive upon or by reason of any
of the events described above, had such share of Series C Stock been converted
into voting Common Stock immediately prior to the occurrence of such event. An
adjustment made pursuant to this paragraph 6(c)(i) shall become effective
retroactively (x) in the case of any such dividend or distribution, to a date
immediately following the close of business on the record date for the
determination of holders of Common Stock entitled to receive such dividend or
distribution, or (y) in the case of any such subdivision, combination or
reclassification, to the close of business on the day upon which such corporate
action becomes effective.



                                     - 4 -
<PAGE>   31

                     (ii)   If the Corporation shall at any time or from time to
time issue or sell any shares of Common Stock or Common Stock Equivalents at a
price per share (the "Offering Price") that is less than the Conversion Price
then in effect as of the record date or Issue Date referred to in the following
sentence, as the case may be (the "Relevant Date") (treating the Offering Price
per share of Common Stock, in the case of the issuance of any Common Stock
Equivalent, as equal to (x) the sum of the price for such Common Stock
Equivalent plus any additional consideration payable (without regard to any
anti-dilution adjustments) upon the conversion, exchange or exercise of such
Common Stock Equivalent, divided by (y) the number of shares of Common Stock
initially underlying such Common Stock Equivalent), other than (1) issuances or
sales for which an adjustment is made pursuant to another paragraph of this
Section 6(c) and (2) issuances of Common Stock in connection with an Excluded
Transaction, then, and in each such case, the Conversion Price then in effect
shall be reduced, concurrently with such issuance, to a price determined by
multiplying such Conversion Price by a fraction, the numerator of which shall be
the number of Shares then outstanding immediately prior to such issuance plus
the number of shares of Common Stock that the aggregate consideration received
by the Corporation for the total number of additional shares of Common Stock or
Common Stock Equivalents so issued would purchase at such Conversion Price; and
the denominator of which shall be the number of Shares then outstanding
immediately prior to such issuance plus the number of such additional shares of
Common Stock or Common Stock Equivalents so issued. Such adjustment shall be
made whenever such shares of Common Stock or Common Stock Equivalents are
issued, and shall become effective retroactively to a date immediately following
the close of business (x) in the case of an issuance to the stockholders of the
Corporation, as such, on the record date for the determination of stockholders
entitled to receive such shares of Common Stock or Common Stock Equivalents and
(y) in all other cases, on the date (the "Issue Date") of such issuance;
provided, however, that the determination as to whether an adjustment is
required to be made pursuant to this Section 6(c)(ii) shall only be made upon
the issuance of such shares of Common Stock or Common Stock Equivalents, and not
upon the issuance of the security into which such Common Stock Equivalents
convert, exchange or may be exercised; and provided further, that if and to the
extent that the convertibility or exercisability feature of such Common Stock
Equivalents expires prior to conversion or exercise thereof, then the Conversion
Price shall be readjusted (but to no greater extent than originally adjusted) to
a Conversion Price equal to that price which would have existed had the expired
Common Stock Equivalents never been issued or sold.

                     (iii)  In the case the Corporation, at any time or from
time to time, shall take any action affecting its Common Stock similar to or
having an effect similar to any of the actions described in paragraphs 6(c)(i)
or (ii) (but not including any action described in any such paragraphs) and the
Board of Directors in good faith determines that it would be equitable in the
circumstances to adjust the Conversion Price as a result of such action, then,
and in each such case, the Conversion Price shall be adjusted in such manner and
at such time as the Board of Directors of the Corporation in good faith
determines would be equitable in the circumstances (such determination to be
evidenced in a resolution, a certified copy of which shall be mailed to the
holders of the shares of Series C Stock).

              (d)    If the Corporation shall take a record of the holders of
its Common Stock for the purpose of entitling them to receive a dividend or
other distribution, and shall thereafter and



                                     - 5 -
<PAGE>   32

before the distribution to stockholders thereof legally abandon its plan to pay
or deliver such dividend or distribution, then thereafter no adjustment in the
Conversion Price then in effect shall be required by reason of the taking of
such record.

              (e)    Upon any increase or decrease in the Conversion Price,
then, and in each such case, the Corporation promptly shall deliver to each
registered holder of Series C Stock at least ten (10) Business Days prior to
effecting any of the foregoing transactions a certificate, signed by the Chief
Executive Officer, Chief Financial Officer, President or a Vice President and by
the Treasurer, an Assistant Treasurer, the Secretary or an Assistant Secretary
of the Corporation, setting forth in reasonable detail the event requiring the
adjustment and the method by which such adjustment was calculated and specifying
the increased or decreased Conversion Price then in effect following such
adjustment.

              (f)    In case at any time or from time to time:

                     (i)    The Corporation shall declare a dividend (or any
other distribution) on its shares of Capital Stock;

                     (ii)   the Corporation shall authorize the granting to the
holders of its Capital Stock of rights or warrants to subscribe for or purchase
any shares of stock of any class or of any other rights or warrants;

                     (iii)  there shall be any reorganization or
reclassification of the Capital Stock of the Corporation, or any merger or
consolidation to which the Corporation is a party and for which approval of any
of the stockholders of the Corporation is required, or any sale or other
disposition of all or substantially all of the assets of the Corporation; or

                     (iv)   there shall occur a Liquidation; then the
Corporation shall mail to each holder of shares of Series C Stock at such
holder's address as it appears on the transfer books of the Corporation, as
promptly as possible but in any event at least thirty (30) days prior to the
applicable date hereinafter specified, a notice stating (A) the date on which a
record is to be taken for the purpose of such dividend, distribution, rights or
warrants or, if a record is not to be taken, the date as of which the holders of
Common Stock of record to be entitled to such dividend, distribution or rights
are to be determined, or (B) the date on which such reclassification,
reorganization, merger, consolidation, sale, disposition or Liquidation is
expected to become effective. Such notice also shall specify the date as of
which it is expected that holders of Common Stock of record shall be entitled to
exchange their Common Stock for shares of stock or other securities or property
or cash deliverable upon such reclassification, reorganization, merger,
consolidation, sale, exchange, transfer or Liquidation.

              (g)    The Corporation shall at all times reserve and keep
available for issuance upon the conversion of the Series C Stock, such number of
its authorized but unissued shares of voting Common Stock as will from time to
time be sufficient to permit the conversion of all outstanding shares of Series
C Stock, and shall take all action required to increase the authorized number of
shares of voting Common Stock if at any time there shall be insufficient
authorized but


                                     - 6 -
<PAGE>   33

unissued shares of voting Common Stock to permit such reservation or to permit
the conversion of all outstanding shares of Series C Stock.

              (h)    The issuance or delivery of certificates for voting Common
Stock upon the conversion of shares of Series C Stock shall be made without
charge to the converting holder of shares of Series C Stock for such
certificates or for any tax in respect of the issuance or delivery of such
certificates or the securities represented thereby, and such certificates shall
be issued or delivered in the respective names of, or (subject to compliance
with the applicable provisions of federal and state securities laws) in such
names as may be directed by, the holders of the shares of Series C Stock
converted; provided, however, that the Corporation shall not be required to pay
any tax which may be payable in respect of any transfer involved in the issuance
and delivery of any such certificate in a name other than that of the holder of
the shares of Series C Stock converted, and the Corporation shall not be
required to issue or deliver such certificate unless or until the Person
requesting the issuance or delivery thereof shall have paid to the Corporation
the amount of such tax or shall have established to the reasonable satisfaction
of the Corporation that such tax has been paid.

       7.     Automatic Conversion. Each share of Series C Stock shall
automatically be converted into such number of fully paid and nonassessable
shares of voting Common Stock at the then applicable Conversion Price in
accordance with Section 6 hereof upon the earlier of (i) the Corporation
achieving average volume of at least five million (5,000,000) shares per day
transacted through its proprietary OptiMark(TM) trading system for the latest
twelve month period and operating profit, as normally recorded on the
Corporation's books and records, over the same twelve month period of at least
$10,000,000, or (ii) immediately after the closing of an underwritten initial
public offering ("IPO") pursuant to an effective registration statement filed
under the Securities Act covering the offer and sale of shares of Common Stock
for the account of the Corporation at a price per share of Common Stock that is
at least 1.67 times (167% of) the then applicable Conversion Price and resulting
in aggregate gross proceeds to the Corporation of at least $10,000,000. In the
event of an IPO, the Person(s) entitled to receive the shares of Common Stock
issuable upon such conversion of the Series C Stock shall not be deemed to have
converted the Series C Stock until immediately after the closing of such
offering, except that any such Person may convert its shares of Series C Stock
at any earlier time in accordance with paragraph 6.

       8.     Certain Remedies. Any registered holder of Series C Stock shall be
entitled to an injunction or injunctions to prevent breaches of the provisions
of this Certificate of Designations and to enforce specifically the terms and
provisions of this Certificate of Designations in any court of the United States
or any state thereof having jurisdiction, this being in addition to any other
remedy to which such holder may be entitled at law or in equity.

       9.     Reissuance of Series C Stock. Shares of Series C Stock that have
been issued and reacquired in any manner, including shares redeemed or
converted, shall (upon compliance with any applicable provisions of the laws of
Delaware) have the status of authorized and unissued shares of Preferred Stock
of the Corporation, undesignated as to series, and may be redesignated and
reissued as part of any series of preferred stock (including Series C Stock).



                                     - 7 -
<PAGE>   34

       10.    Amendment. This Certificate of Designations may be amended with
(and only with) the written consent of (i) the Corporation, and (ii) the holders
of not less than 75% of the outstanding shares of Series C Stock.

       11.    Definitions. As used in this Certificate of Designation, in
addition to other capitalized terms defined elsewhere in this Certificate, the
following terms shall have the following meanings (with terms defined in the
singular having comparable meanings when used in the plural and vice versa),
unless the context otherwise requires:

              "Board of Directors" means the Board of Directors of the
Corporation.

              "Capital Stock" means, with respect to any Person, any and all
shares, interests, participations, rights in, or other equivalents (however
designated and whether voting or nonvoting) of such Person's capital stock and
any and all rights, warrants or options exchangeable for or convertible into
such capital stock.

              "Commission" means the Securities and Exchange Commission or any
similar agency then having jurisdiction to enforce the Securities Act.

              "Common Stock" means the Corporation's common stock (including
both voting and nonvoting common stock), $.01 par value per share.

              "Common Stock Equivalents" means any security or obligation which
is by its terms convertible into or exchangeable for shares of Common Stock,
including, without limitation, the Series A Stock, the Series B Stock, the
Series C Stock and any option, warrant or other subscription or purchase right
with respect to shares of Common Stock.

              "Exchange Act" means the Securities Exchange Act of 1934, and the
rules and regulations of the Commission promulgated thereunder.

              "Excluded Transaction" shall mean (i) the issuance of shares
directly to, the issuance of Common Stock Equivalents to, and the issuance of
shares upon the exercise, exchange or conversion of Common Stock Equivalents
granted to the Corporation's officers, directors, employees, former employees
and consultants, as incentives, (ii) the issuance of Common Stock pursuant to a
warrant in favor of The Pacific Exchange, Incorporated dated August 27, 1996,
(subject to adjustment as provided therein), (iii) the issuance of Common Stock
pursuant to a warrant in favor of The Chicago Board Options Exchange,
Incorporated dated December 31, 1996 (subject to adjustment as provided
therein), (iv) the issuance of Common Stock pursuant to a warrant in favor of
Virginia Surety Company, Inc. dated April 23, 1998 (subject to adjustment as
provided therein) (v) the issuance of Common Stock pursuant to a warrant in
favor of Transamerica Business Credit Corporation dated June 19, 1998 (subject
to adjustment as provided therein), (vi) the issuance of Common Stock pursuant
to a warrant in favor of Francis X. Egan dated August 24, 1998 (subject to
adjustment as provided therein) (vii) the issuance of Common Stock pursuant to a
warrant in favor of The Nasdaq Stock Market, Inc. dated September 1, 1998
(subject to adjustment as provided therein), (viii) the issuance of Common Stock
pursuant to a warrant in favor of Ramsey Beirne, L.L.C. dated



                                     - 8 -
<PAGE>   35

November 2, 1998 (subject to adjustment as provided therein), (ix) the issuance
of Common Stock pursuant to a warrant in favor of BIOS Group, L.P. dated January
27, 1999 (subject to adjustment as provided therein), (x) the issuance of Common
Stock pursuant to a warrant in favor of Goldman Sachs Group, Inc. dated May 7,
1999 (subject to adjustment as provided therein), (xi) the issuance of Common
Stock pursuant to a warrant in favor of BT Investment Partners, Inc. dated May
7, 1999 (subject to adjustment as provided therein), (xii) the issuance of
Common Stock pursuant to those warrants in favor of ML IBK Positions, Inc.,
Merrill Lynch KECALP International L.P. 1997 and Merrill Lynch KECALP L.P. 1997,
each dated May 7, 1999 (and each subject to adjustment as provided therein)
(xiii) the issuance of Common Stock upon conversion of the Series A Stock, (xiv)
the issuance of Common Stock upon conversion of the Series B Stock, and (xv) the
issuance of voting Common Stock upon conversion of the Corporation's non-voting
Common Stock.

              "Fair Market Value" shall mean the amount which a willing buyer
would pay a willing seller in an arm's length transaction as determined in good
faith by the Board of Directors.

              "Person" means any individual, firm, corporation, partnership,
limited liability company, trust, incorporated or unincorporated association,
joint venture, joint stock company, governmental body or other entity of any
kind.

              "Securities Act" means the Securities Act of 1933, as amended, and
the rules and regulations of the Commission promulgated thereunder.

              "Shares outstanding" or "Shares then outstanding" means all shares
of Common Stock outstanding and all shares of Common Stock issuable upon
conversion, exercise or exchange of any option, warrant or other security or
obligation which is, by its terms, convertible, exercisable or exchangeable into
shares of Common Stock, whether or not such conversion, exercise or exchange has
actually been effected.



                                     - 9 -
<PAGE>   36




              IN WITNESS WHEREOF, the Corporation has caused this certificate to
be duly executed by its Chief Executive Officer this 9th day of June, 2000


                                        OPTIMARK HOLDINGS, INC.


                                        By:  /s/  Phillip J. Riese
                                                    Chief Executive Officer


                                     - 10 -
<PAGE>   37
                      CERTIFICATE OF POWERS, DESIGNATIONS,

                          PREFERENCES AND RIGHTS OF THE

                      SERIES D CONVERTIBLE PREFERRED STOCK,

                            PAR VALUE $.01 PER SHARE
             Pursuant to Section 151 of the General Corporation Law
                            of the State of Delaware

       The following resolution was duly adopted by the Board of Directors of
OptiMark Holdings, Inc., a Delaware corporation (the "Corporation"), pursuant to
the provisions of Section 151 of the General Corporation Law of the State of
Delaware, effective as of June 9, 2000, by unanimous written consent of the
Board of Directors.

       WHEREAS, the Board of Directors is authorized, within the limitations and
restrictions stated in the Amended and Restated Certificate of Incorporation of
the Corporation, (the "Certificate of Incorporation") to provide by resolution
or resolutions for the issuance of shares of Preferred Stock, par value $.01 per
share, of the Corporation, in one or more classes or series with such voting
powers, full or limited, or without voting powers, and such designations,
preferences and relative, participating, optional or other special rights, and
qualifications, limitations or restrictions as shall be stated and expressed in
the resolution or resolutions providing for the issuance thereof adopted by the
Board of Directors, and as are not stated and expressed in the Certificate of
Incorporation, or any amendment thereto, including (but without limiting the
generality of the foregoing) such provisions as may be desired concerning
voting, redemption, dividends, dissolution or the distribution of assets and
such other subjects or matters as may be fixed by resolution or resolutions of
the Board of Directors under the General Corporation Law of the State of
Delaware; and

       WHEREAS, it is the desire of the Board of Directors, pursuant to its
authority as aforesaid, to authorize and fix the terms of a series of preferred
stock and the number of shares constituting such series.

       NOW THEREFORE, BE IT RESOLVED:

       1.     Designation and Number of Shares. There is hereby established a
series of Preferred Stock of the Corporation designated as "Series D Convertible
Preferred Stock" (the "Series D Stock"). The authorized number of shares of
Series D Stock shall be two hundred fifty thousand (250,000).

       2.     Dividends.


<PAGE>   38

              (a)    If the Board of Directors of the Corporation shall declare
a dividend or make any other distribution (including, without limitation, in
cash, evidences of indebtedness of the Corporation or another issuer, securities
of the Corporation other than Common Stock or another issuer, or other property
or assets), to holders of shares of Common Stock, then the holder of each share
of Series D Stock theretofore issued shall be entitled to receive, out of funds
legally available therefor, a dividend or distribution in an amount equal to the
amount of such dividend or distribution received by a holder of the number of
shares of Common Stock for which such share of Series D Stock is convertible on
the record date for such dividend or distribution. Any such amount shall be paid
to the holders of shares of Series D Stock at the same time such dividend or
distribution is made to holders of Common Stock.

              (b)    Except as otherwise provided in paragraph (a) above, the
Series D Stock shall not be entitled to any dividends.

       3.     Liquidation Preference.

              (a)    In connection with any Liquidation of the Corporation, (i)
if the assets of the Corporation available for distribution to the stockholders
are sufficient to pay the Series A Liquidation Amount with respect to each
outstanding share of Series A Stock, to pay the Series B Liquidation Amount with
respect to each outstanding share of Series B Stock, to pay the Series C
Liquidation Amount with respect to each outstanding share of Series C Stock and
to pay the Series D Liquidation Amount with respect to each outstanding share of
Series D Stock, then the holders of Series D Stock then outstanding shall be
entitled to be paid the Series D Liquidation Amount for each share of Series D
Stock held thereby before any payment shall be made or any assets distributed to
the holders of any shares of Junior Stock (as hereinafter defined), (ii) if the
assets of the Corporation available for distribution to the stockholders are not
sufficient to pay the Series A Liquidation Amount, the Series B Liquidation
Amount, the Series C Liquidation Amount and the Series D Liquidation Amount,
then the holders of the outstanding shares of Series A Stock, Series B Stock,
Series C Stock and Series D Stock shall share pari passu in the distribution of
available assets, pro rata to the amounts that would have been payable to such
holders if the assets of the Corporation available for distribution to the
stockholders in Liquidation had been sufficient to pay the Series A Liquidation
Amount, the Series B Liquidation Amount, the Series C Liquidation Amount and the
Series D Liquidation Amount in full, and (iii) the Series D Liquidation Amount
must be paid in full with respect to each outstanding share of Series D Stock
before any payment shall be made or any assets distributed to the holders of any
shares of Common Stock or any other securities which, by their terms, have
expressly been made junior to the Series D Stock in Liquidation (the "Junior
Stock").

              (b)    Written notice of any Liquidation, stating a payment date,
the amount of the payment determined pursuant to this paragraph 3 and the place
where such amount shall be payable, shall be delivered in person, mailed by
certified or registered mail, return receipt requested, mailed by overnight mail
or sent by telecopier, not less than ten (10) days prior to the payment date
stated therein, to the holders of record of the Series D Stock, such notice to
be addressed to each such holder at its address as shown by the records of the
Corporation.


                                     - 2 -
<PAGE>   39

              (c)    The fair value of the assets to be distributed or exchanged
(to the extent that distributions are not made in cash) in the event of
Liquidation shall be determined as provided in the Certificate of Designations
on file with the Delaware Secretary of State with respect to the Series A Stock
(the "Series A Certificate").

              (d)    For purposes of this Certificate of Designations, (i)
"Liquidation" means any voluntary or involuntary liquidation, dissolution or
winding-up of the Corporation, under the U.S. Bankruptcy Code or otherwise, (ii)
"Series A Stock" means the Corporation's Series A Convertible Participating
Preferred Stock, $.01 par value, (iii) the "Series A Liquidation Amount" means
the amount payable upon Liquidation to the holders of the Series A Stock, as
provided in the Series A Certificate, (iv) "Series B Stock" means the
Corporation's Series B Convertible Participating Preferred Stock, $.01 par
value, (v) the "Series B Liquidation Amount" means the amount payable upon
Liquidation to the holders of the Series B Stock, as provided in the Certificate
of Designations on file with the Delaware Secretary of State with respect to the
Series B Stock, (vi) "Series C Stock" means the Corporation's Series C
Convertible Preferred Stock, $.01 par value, (vii) the "Series C Liquidation
Amount" means the amount payable upon Liquidation to the holders of the Series C
Stock, as provided in the Certificate of Designations on file with the Delaware
Secretary of State with respect to the Series C Stock, and (viii) the "Series D
Liquidation Amount" means $12.00 per share of Series D Stock plus all declared
and unpaid dividends thereon (if any) through the effective date of Liquidation.

       4.     Redemption. The shares of Series D Stock shall not be redeemable
at the option of the Corporation or at the option of any holder thereof.

       5.     Voting Rights; Election of Directors. Each issued and outstanding
share of Series D Stock shall entitle the holder thereof to vote, in person or
by proxy, at each special and annual meeting of stockholders of the Corporation,
on all matters entitled to be voted on by holders of voting Common Stock. To the
maximum extent permitted by law, on all matters submitted to a vote of the
stockholders, the holders of the Series D Stock shall vote as a single class
together with the holders of voting Common Stock and with all other shares
(including the outstanding shares of Series A Stock, Series B Stock and Series C
Stock) entitled to vote with the voting Common Stock thereon. With respect to
any such vote, each share of Series D Stock shall entitle the holder thereof to
cast that number of votes per share as is equal to the number of votes that such
holder would be entitled to cast had such holder converted its shares of Series
D Stock into shares of Common Stock on the record date for determining the
stockholders of the Corporation eligible to vote on such matters.

       6.     Conversion.

              (a)    Any holder of Series D Stock shall have the right, at its
option, at any time and from time to time, to convert, subject to the terms and
provisions of this paragraph 6, any or all of such holder's shares of Series D
Stock into such number of fully paid and nonassessable shares of voting Common
Stock as is equal to the product of the number of shares of Series D Stock being
so converted multiplied by the quotient of (i) the Liquidation Amount, divided
by (ii) the conversion price of $12.00 per share, subject to adjustment as
provided in paragraph 6(c) (the "Conversion Price"), then in effect. Such
conversion right shall be exercised by the surrender of the shares of



                                     - 3 -
<PAGE>   40

Series D Stock to be converted to the Corporation at any time during usual
business hours at its principal place of business to be maintained by it,
accompanied by written notice that the holder elects to convert such shares of
Series D Stock and specifying the name or names (with address) in which a
certificate or certificates for shares of voting Common Stock are to be issued
and (if so required by the Corporation) by a written instrument or instruments
of transfer in form reasonably satisfactory to the Corporation duly executed by
the holder or its duly authorized legal representative and transfer tax stamps
or funds therefor, if required pursuant to paragraph 6(h).

              (b)    As promptly as practicable after the surrender, as herein
provided, of any shares of Series D Stock for conversion pursuant to paragraph
6(a), the Corporation shall deliver to or per the written order of the holder of
such shares of Series D Stock so surrendered a certificate or certificates
representing the number of fully paid and nonassessable shares of voting Common
Stock into which such shares of Series D Stock may be or have been converted in
accordance with the provisions of this paragraph 6. Subject to the following
provisions of this paragraph and of paragraph 6(c), such conversion shall be
deemed to have been made immediately prior to the close of business on the date
that such shares of Series D Stock shall have been surrendered in satisfactory
form for conversion, and the Person or Persons entitled to receive the shares of
voting Common Stock deliverable upon conversion of such shares of Series D Stock
shall be treated for all purposes as having become the record holder or holders
of such shares of voting Common Stock at such appropriate time, and such
conversion shall be at the Conversion Price in effect at such time; provided,
however, that no surrender shall be effective to constitute the Person or
Persons entitled to receive the shares of voting Common Stock deliverable upon
such conversion as the record holder or holders of such shares of voting Common
Stock while the share transfer books of the Corporation shall be closed (but not
for any period in excess of five days), but such surrender shall be effective to
constitute the Person or Persons entitled to receive such shares of voting
Common Stock as the record holder or holders thereof for all purposes
immediately prior to the close of business on the next succeeding day on which
such share transfer books are open, and such conversion shall be deemed to have
been made at, and shall be made at the Conversion Price in effect at, such time
on such next succeeding day.

              (c)    The Conversion Price shall be subject to adjustment as
follows:

                     (i)    In the event that the Corporation shall at any time
or from time to time (w) pay a dividend or make a distribution (other than a
dividend or distribution paid or made to holders of shares of Series D Stock in
the manner provided in paragraph 2) on the outstanding shares of Common Stock in
Capital Stock, (x) subdivide the outstanding shares of Common Stock into a
larger number of shares, (y) combine the outstanding shares of Common Stock into
a smaller number of shares or (z) issue any shares of its Capital Stock in a
reclassification of the Common Stock, then, and in each such case, the
Conversion Price in effect immediately prior to such event shall be adjusted
(and any other appropriate actions shall be taken by the Corporation) so that
the holder of any share of Series D Stock thereafter surrendered for conversion
shall be entitled to receive the number of shares of voting Common Stock or
other securities of the Corporation that such holder would have owned or to
which such holder would have been entitled to receive upon or by reason of any
of the events described above, had such share of Series D Stock been converted
into voting Common Stock immediately prior to the occurrence of such event. An
adjustment made pursuant to this paragraph 6(c)(i) shall become effective
retroactively (x) in the case of any such



                                     - 4 -
<PAGE>   41

dividend or distribution, to a date immediately following the close of business
on the record date for the determination of holders of Common Stock entitled to
receive such dividend or distribution, or (y) in the case of any such
subdivision, combination or reclassification, to the close of business on the
day upon which such corporate action becomes effective.

                     (ii)   If the Corporation shall at any time or from time to
time issue or sell any shares of Common Stock or Common Stock Equivalents at a
price per share (the "Offering Price") that is less than the Conversion Price
then in effect as of the record date or Issue Date referred to in the following
sentence, as the case may be (the "Relevant Date") (treating the Offering Price
per share of Common Stock, in the case of the issuance of any Common Stock
Equivalent, as equal to (x) the sum of the price for such Common Stock
Equivalent plus any additional consideration payable (without regard to any
anti-dilution adjustments) upon the conversion, exchange or exercise of such
Common Stock Equivalent, divided by (y) the number of shares of Common Stock
initially underlying such Common Stock Equivalent), other than (1) issuances or
sales for which an adjustment is made pursuant to another paragraph of this
Section 6(c) and (2) issuances of Common Stock in connection with an Excluded
Transaction, then, and in each such case, the Conversion Price then in effect
shall be reduced, concurrently with such issuance, to a price determined by
multiplying such Conversion Price by a fraction, the numerator of which shall be
the number of Shares then outstanding immediately prior to such issuance plus
the number of shares of Common Stock that the aggregate consideration received
by the Corporation for the total number of additional shares of Common Stock or
Common Stock Equivalents so issued would purchase at such Conversion Price; and
the denominator of which shall be the number of Shares then outstanding
immediately prior to such issuance plus the number of such additional shares of
Common Stock or Common Stock Equivalents so issued. Such adjustment shall be
made whenever such shares of Common Stock or Common Stock Equivalents are
issued, and shall become effective retroactively to a date immediately following
the close of business (x) in the case of an issuance to the stockholders of the
Corporation, as such, on the record date for the determination of stockholders
entitled to receive such shares of Common Stock or Common Stock Equivalents and
(y) in all other cases, on the date (the "Issue Date") of such issuance;
provided, however, that the determination as to whether an adjustment is
required to be made pursuant to this Section 6(c)(ii) shall only be made upon
the issuance of such shares of Common Stock or Common Stock Equivalents, and not
upon the issuance of the security into which such Common Stock Equivalents
convert, exchange or may be exercised; and provided further, that if and to the
extent that the convertibility or exercisability feature of such Common Stock
Equivalents expires prior to conversion or exercise thereof, then the Conversion
Price shall be readjusted (but to no greater extent than originally adjusted) to
a Conversion Price equal to that price which would have existed had the expired
Common Stock Equivalents never been issued or sold.

                     (iii)  In the case the Corporation, at any time or from
time to time, shall take any action affecting its Common Stock similar to or
having an effect similar to any of the actions described in paragraphs 6(c)(i)
or (ii) (but not including any action described in any such paragraphs) and the
Board of Directors in good faith determines that it would be equitable in the
circumstances to adjust the Conversion Price as a result of such action, then,
and in each such case, the Conversion Price shall be adjusted in such manner and
at such time as the Board of Directors of the Corporation in good faith
determines would be equitable in the circumstances (such



                                     - 5 -
<PAGE>   42

determination to be evidenced in a resolution, a certified copy of which shall
be mailed to the holders of the shares of Series D Stock).

              (d)    If the Corporation shall take a record of the holders of
its Common Stock for the purpose of entitling them to receive a dividend or
other distribution, and shall thereafter and before the distribution to
stockholders thereof legally abandon its plan to pay or deliver such dividend or
distribution, then thereafter no adjustment in the Conversion Price then in
effect shall be required by reason of the taking of such record.

              (e)    Upon any increase or decrease in the Conversion Price,
then, and in each such case, the Corporation promptly shall deliver to each
registered holder of Series D Stock at least ten (10) Business Days prior to
effecting any of the foregoing transactions a certificate, signed by the Chief
Executive Officer, Chief Financial Officer, President or a Vice President and by
the Treasurer, an Assistant Treasurer, the Secretary or an Assistant Secretary
of the Corporation, setting forth in reasonable detail the event requiring the
adjustment and the method by which such adjustment was calculated and specifying
the increased or decreased Conversion Price then in effect following such
adjustment.

              (f)    In case at any time or from time to time:

                     (i)    The Corporation shall declare a dividend (or any
other distribution) on its shares of Capital Stock;

                     (ii)   the Corporation shall authorize the granting to the
holders of its Capital Stock of rights or warrants to subscribe for or purchase
any shares of stock of any class or of any other rights or warrants;

                     (iii)  there shall be any reorganization or
reclassification of the Capital Stock of the Corporation, or any merger or
consolidation to which the Corporation is a party and for which approval of any
of the stockholders of the Corporation is required, or any sale or other
disposition of all or substantially all of the assets of the Corporation; or

                     (iv)   there shall occur a Liquidation;

then the Corporation shall mail to each holder of shares of Series D Stock at
such holder's address as it appears on the transfer books of the Corporation, as
promptly as possible but in any event at least thirty (30) days prior to the
applicable date hereinafter specified, a notice stating (A) the date on which a
record is to be taken for the purpose of such dividend, distribution, rights or
warrants or, if a record is not to be taken, the date as of which the holders of
Common Stock of record to be entitled to such dividend, distribution or rights
are to be determined, or (B) the date on which such reclassification,
reorganization, merger, consolidation, sale, disposition or Liquidation is
expected to become effective. Such notice also shall specify the date as of
which it is expected that holders of Common Stock of record shall be entitled to
exchange their Common Stock for shares of stock or other securities or property
or cash deliverable upon such reclassification, reorganization, merger,
consolidation, sale, exchange, transfer or Liquidation.

              (g)    The Corporation shall at all times reserve and keep
available for issuance upon the conversion of the Series D Stock, such number of
its authorized but unissued shares of



                                     - 6 -
<PAGE>   43

voting Common Stock as will from time to time be sufficient to permit the
conversion of all outstanding shares of Series D Stock, and shall take all
action required to increase the authorized number of shares of voting Common
Stock if at any time there shall be insufficient authorized but unissued shares
of voting Common Stock to permit such reservation or to permit the conversion of
all outstanding shares of Series D Stock.

              (h)    The issuance or delivery of certificates for voting Common
Stock upon the conversion of shares of Series D Stock shall be made without
charge to the converting holder of shares of Series D Stock for such
certificates or for any tax in respect of the issuance or delivery of such
certificates or the securities represented thereby, and such certificates shall
be issued or delivered in the respective names of, or (subject to compliance
with the applicable provisions of federal and state securities laws) in such
names as may be directed by, the holders of the shares of Series D Stock
converted; provided, however, that the Corporation shall not be required to pay
any tax which may be payable in respect of any transfer involved in the issuance
and delivery of any such certificate in a name other than that of the holder of
the shares of Series D Stock converted, and the Corporation shall not be
required to issue or deliver such certificate unless or until the Person
requesting the issuance or delivery thereof shall have paid to the Corporation
the amount of such tax or shall have established to the reasonable satisfaction
of the Corporation that such tax has been paid.

       7.     Automatic Conversion. Each share of Series D Stock shall
automatically be converted into such number of fully paid and nonassessable
shares of voting Common Stock at the then applicable Conversion Price in
accordance with Section 6 hereof upon the earlier of (i) the Corporation
achieving average volume of at least five million (5,000,000) shares per day
transacted through its proprietary OptiMark(TM) trading system for the latest
twelve month period and operating profit, as normally recorded on the
Corporation's books and records, over the same twelve month period of at least
$10,000,000, or (ii) immediately after the closing of an underwritten initial
public offering ("IPO") pursuant to an effective registration statement filed
under the Securities Act covering the offer and sale of shares of Common Stock
for the account of the Corporation at a price per share of Common Stock that is
at least 1.67 times (167% of) the then applicable Conversion Price and resulting
in aggregate gross proceeds to the Corporation of at least $10,000,000. In the
event of an IPO, the Person(s) entitled to receive the shares of Common Stock
issuable upon such conversion of the Series D Stock shall not be deemed to have
converted the Series D Stock until immediately after the closing of such
offering, except that any such Person may convert its shares of Series D Stock
at any earlier time in accordance with paragraph 6.

       8.     Certain Remedies. Any registered holder of Series D Stock shall be
entitled to an injunction or injunctions to prevent breaches of the provisions
of this Certificate of Designations and to enforce specifically the terms and
provisions of this Certificate of Designations in any court of the United States
or any state thereof having jurisdiction, this being in addition to any other
remedy to which such holder may be entitled at law or in equity.

       9.     Reissuance of Series D Stock. Shares of Series D Stock that have
been issued and reacquired in any manner, including shares redeemed or
converted, shall (upon compliance with any applicable provisions of the laws of
Delaware) have the status of authorized and unissued shares of



                                     - 7 -
<PAGE>   44

Preferred Stock of the Corporation, undesignated as to series, and may be
redesignated and reissued as part of any series of preferred stock (including
Series D Stock).

       10.    Amendment. This Certificate of Designations may be amended with
(and only with) the written consent of (i) the Corporation, and (ii) the holders
of not less than 75% of the outstanding shares of Series D Stock.

       11.    Definitions. As used in this Certificate of Designation, in
addition to other capitalized terms defined elsewhere in this Certificate, the
following terms shall have the following meanings (with terms defined in the
singular having comparable meanings when used in the plural and vice versa),
unless the context otherwise requires:

              "Board of Directors" means the Board of Directors of the
Corporation.

              "Capital Stock" means, with respect to any Person, any and all
shares, interests, participations, rights in, or other equivalents (however
designated and whether voting or nonvoting) of such Person's capital stock and
any and all rights, warrants or options exchangeable for or convertible into
such capital stock.

              "Commission" means the Securities and Exchange Commission or any
similar agency then having jurisdiction to enforce the Securities Act.

              "Common Stock" means the Corporation's common stock (including
both voting and nonvoting common stock), $.01 par value per share.

              "Common Stock Equivalents" means any security or obligation which
is by its terms convertible into or exchangeable for shares of Common Stock,
including, without limitation, the Series A Stock, the Series B Stock, the
Series C Stock, the Series D Stock and any option, warrant or other subscription
or purchase right with respect to shares of Common Stock.

              "Exchange Act" means the Securities Exchange Act of 1934, and the
rules and regulations of the Commission promulgated thereunder.

              "Excluded Transaction" shall mean (i) the issuance of shares
directly to, the issuance of Common Stock Equivalents to, and the issuance of
shares upon the exercise, exchange or conversion of Common Stock Equivalents
granted to the Corporation's officers, directors, employees, former employees
and consultants, as incentives, (ii) the issuance of Common Stock pursuant to a
warrant in favor of The Pacific Exchange, Incorporated dated August 27, 1996,
(subject to adjustment as provided therein), (iii) the issuance of Common Stock
pursuant to a warrant in favor of The Chicago Board Options Exchange,
Incorporated dated December 31, 1996 (subject to adjustment as provided
therein), (iv) the issuance of Common Stock pursuant to a warrant in favor of
Virginia Surety Company, Inc. dated April 23, 1998 (subject to adjustment as
provided therein) (v) the issuance of Common Stock pursuant to a warrant in
favor of Transamerica Business Credit Corporation dated June 19, 1998 (subject
to adjustment as provided therein), (vi) the issuance of Common Stock pursuant
to a warrant in favor of Francis X. Egan dated August 24, 1998 (subject to
adjustment as provided therein) (vii) the issuance of Common Stock pursuant to a
warrant in favor of The Nasdaq Stock Market, Inc. dated September 1, 1998
(subject to adjustment as provided therein),




                                     - 8 -
<PAGE>   45

(viii) the issuance of Common Stock pursuant to a warrant in favor of Ramsey
Beirne, L.L.C. dated November 2, 1998 (subject to adjustment as provided
therein), (ix) the issuance of Common Stock pursuant to a warrant in favor of
BIOS Group, L.P. dated January 27, 1999 (subject to adjustment as provided
therein), (x) the issuance of Common Stock upon conversion of the Series A
Stock, (xi) the issuance of Common Stock upon conversion of the Series B Stock,
(xii) the issuance of Common Stock upon conversion of the Series C Stock, and
(xiii) the issuance of voting Common Stock upon conversion of the Corporation's
non-voting Common Stock.

              "Fair Market Value" shall mean the amount which a willing buyer
would pay a willing seller in an arm's length transaction as determined in good
faith by the Board of Directors.

              "Person" means any individual, firm, corporation, partnership,
limited liability company, trust, incorporated or unincorporated association,
joint venture, joint stock company, governmental body or other entity of any
kind.

              "Securities Act" means the Securities Act of 1933, as amended, and
the rules and regulations of the Commission promulgated thereunder.

              "Shares outstanding" or "Shares then outstanding" means all shares
of Common Stock outstanding and all shares of Common Stock issuable upon
conversion, exercise or exchange of any option, warrant or other security or
obligation which is, by its terms, convertible, exercisable or exchangeable into
shares of Common Stock, whether or not such conversion, exercise or exchange has
actually been effected.



                                     - 9 -
<PAGE>   46




              IN WITNESS WHEREOF, the Corporation has caused this certificate to
be duly executed by its Chief Executive Officer this 9th day of June, 2000

                                  OPTIMARK HOLDINGS, INC.


                                  By:  /s/ Phillip J. Riese
                                              Chief Executive Officer



                                     - 10 -
<PAGE>   47
                            CERTIFICATE OF AMENDMENT
                                     OF THE
                          CERTIFICATE OF INCORPORATION
                                       OF
                          OPTIMARK TECHNOLOGIES, INC.


     OptiMark Technologies, Inc. (the "Company"), a corporation organized and
existing under the General Corporation Law of the State of Delaware, hereby
certifies as follows:

     1.  The First Article of the Certificate of Incorporation of the Company is
hereby amended by deleting the paragraph in its entirety and replacing it with
the following:

         1.  Name. The name of the Corporation is: OptiMark Holdings, Inc.

     2.  Such amendment has been duly adopted in accordance with the provisions
of Sections 141, 242 and 228 of the General Corporation Law of the State of
Delaware by the unanimous written consent of the Board of Directors of the
Company and by the written consent of the holders of shares of the Company
representing a majority of the votes outstanding and entitled to vote. Written
notice has been given to the stockholders who have not consented in writing.

         IN WITNESS WHEREOF, the undersigned has executed this Certificate of
Amendment as of June 16, 2000.


                                          OPTIMARK TECHNOLOGIES, INC.



                                          By:  /s/ James G. Rickards
                                               -----------------------
                                               Name: James G. Rickards
                                               Title: Secretary


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