PLUMTREE SOFTWARE INC
S-1, EX-4.8, 2000-09-18
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                                                                     EXHIBIT 4.8

THE SECURITIES REPRESENTED HEREBY HAVE NOT BEEN REGISTERED UNDER THE SECURITIES
ACT OF 1933, AS AMENDED (THE "ACT"), OR UNDER THE SECURITIES LAWS OF ANY STATE.
THESE SECURITIES ARE SUBJECT TO RESTRICTIONS ON TRANSFERABILITY AND RESALE AND
MAY NOT BE TRANSFERRED OR RESOLD EXCEPT AS PERMITTED UNDER THE ACT AND THE
APPLICABLE STATE SECURITIES LAWS, PURSUANT TO REGISTRATION OR EXEMPTION
THEREFROM. THE ISSUER OF THESE SECURITIES MAY REQUIRE AN OPINION OF COUNSEL IN
FORM AND SUBSTANCE SATISFACTORY TO THE ISSUER TO THE EFFECT THAT ANY PROPOSED
TRANSFER OR RESALE IS IN COMPLIANCE WITH THE ACT AND ANY APPLICABLE STATE
SECURITIES LAWS.

                            PLUMTREE SOFTWARE, INC.
              Warrant for the Purchase of Shares of Common Stock

No. WS-2                                                          100,000 Shares

      FOR VALUE RECEIVED, Plumtree Software, Inc., a California corporation (the
"Company"), with its principal office at 500 Sansome Street, San Francisco,
California 94111, hereby certifies that Procter & Gamble or its registered
assigns (the "Holder") is entitled, subject to the provisions of this Warrant,
to purchase from the Company, the number of fully paid and nonassessable shares
of Common Stock of the Company set forth above.

      This Warrant shall be exercisable, as provided in Section 2, on or before
5:00 p.m. local time on September 30, 2000; provided, however, that in the event
of (a) the closing of the issuance and sale of shares of Common Stock of the
Company in the Company's first underwritten public offering pursuant to an
effective registration statement under the Securities Act of 1933, as amended
(the "IPO"), (b) the closing of the Company's sale or transfer of all or
substantially all of its assets, or (c) the closing of the acquisition of the
Company by means of merger or other form of corporate reorganization in which
outstanding shares of the Company are exchanged for securities or other
consideration issued, or caused to be issued, by the acquiring corporation or
its subsidiary (other than a mere reincorporation transaction), this Warrant
shall, on the date of such event, no longer be exercisable and become null and
void. In the event of a proposed transaction of the kind described above, the
Company shall notify the holder of the Warrant at least fifteen (15) days prior
to the closing of such event or transaction.

                                       2
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      The Holder may purchase the above number of shares of Common Stock at a
purchase price per share (as appropriately adjusted pursuant to Section 6
hereof) of two dollars ($2.00) (the "Exercise Price"). The term "Common Stock"
shall mean the aforementioned Common Stock of the Company, together with any
other equity securities that may be issued by the Company in addition thereto or
in substitution therefor as provided herein.

      The number of shares of Common Stock to be received upon the exercise of
this Warrant and the price to be paid for a share of Common Stock are subject to
adjustment from time to time as hereinafter set forth. The shares of Common
Stock deliverable upon such exercise, as adjusted from time to time, are
hereinafter sometimes referred to as "Warrant Shares".

      This Warrant is subject to all the provisions of that certain Warrant
Agreement between Holder and the Company, dated _____________, 2000 (the
"Agreement"), pursuant to which this Warrant was issued. A copy of the Agreement
may be obtained from the principal offices of the Company located at the address
listed above.


      Section 2.  Exercise of Warrant.
                  -------------------

            (1)   Twenty Thousand (20,000) Warrant Shares shall vest on the
first day of each month for each of the ensuing five months from the date
hereof. Notwithstanding the foregoing, any unvested Warrant Shares will cease to
vest immediately upon written notice by the Company to the Holder of a material
breach under the Development Agreement between the Company and the Holder.
Notwithstanding the foregoing, any unvested Warrant Shares that have ceased to
vest due to such written notice by the Company shall immediately vest pursuant
to a settlement by the parties that so provides or upon a finding by a court or
arbitrator that there was no such material breach. In addition, all Warrant
Shares shall immediately vest upon the 15-day notice provided to the Holder of
such event or transaction as specified above.

                                       3
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            (2)   This Warrant may be exercised in whole or in part on any
business day prior to the termination of the Warrant by presentation and
surrender hereof to the Company at its principal office at the address set forth
in the initial paragraph hereof (or at such other address as the Company may
hereafter notify the Holder in writing) with the Purchase Form annexed hereto
duly executed and accompanied by proper payment of the Exercise Price (i) in
lawful money of the United States of America in the form of a certified or
cashier's check (ii) by cancellation by the Holder of indebtedness or other
obligation of the Company to the Holder, or (iii) by a combination of (i) and
(ii), for the number of Warrant Shares specified in the Purchase Form. If this
Warrant should be exercised in part only, the Company shall, upon surrender of
this Warrant, execute and deliver a new Warrant evidencing the rights of the
Holder thereof to purchase the balance of the Warrant Shares purchasable
hereunder. Upon receipt by the Company of this Warrant and such Purchase Form,
together with proper payment of the Exercise Price, at such office, the Holder
shall be deemed to be the holder of record of the Warrant Shares,
notwithstanding that the stock transfer books of the Company shall then be
closed or that certificates representing such Warrant Shares shall not then be
actually delivered to the Holder. The Company shall pay any and all documentary
stamp or similar issue or transfer taxes payable in respect of the issue or
delivery of the Warrant Shares.

            (3)   Notwithstanding the foregoing, upon such exercise pursuant to
Section 1(a), in lieu of payment of the Exercise Price, the Holder may instead
elect to receive that number of shares of Common Stock of the Company equal to
the quotient obtained by dividing [(A-B)(C)] by A, where:

            (A)  =   the Fair Market Value (as defined below) of one share of
                     Common Stock on the date of exercise of this Warrant;

            (B)  =   the Exercise Price for one share of Common Stock under this
                     Warrant (as adjusted to the date of such calculation); and

            (C)  =   the number of shares of Common Stock issuable upon exercise
                     of this Warrant or, if only a portion of the Warrant is
                     being exercised, the portion of the Warrant being canceled
                     (at the date of such calculation).

If the above calculation results in a negative number, then no shares of Common
Stock shall be issued or issuable upon exercise of this Warrant pursuant to this
Section 1(b).

      For purposes hereof, "Fair Market Value" of a share of Common Stock shall
mean:

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               (1)  where there exists a public market for the Company's Common
Stock at the time of such exercise, the fair market value per share of Common
Stock shall be the average of the closing bid and asked prices of the Common
Stock quoted in the Over-The-Counter Market Summary or the last reported sale
price of the Common Stock or the closing sale price quoted on the NASDAQ
National Market System or on any exchange on which the Common Stock is listed,
whichever is applicable. Notwithstanding the forgoing, in the event the Warrant
is exercised in connection with the Company's initial public offering of Common
Stock ("IPO"), the fair market value per share shall be the per share initial
offering price to the public of the Company's IPO, or

               (2)  in all other cases, the fair value as determined in good
faith by the Company's Board of Directors.

      Upon exercise of this Warrant pursuant to this Section 1(b), the
registered holder hereof shall be entitled to receive a certificate for the
number of shares of Common Stock determined as aforesaid within a reasonable
time not to exceed 20 days after exercise of the stock purchase rights
represented by this Warrant.

          Section 3.  Reservation of Shares. The Company hereby agrees that at
                      ---------------------
all times there shall be reserved for issuance and delivery upon exercise of
this Warrant all shares of its Common Stock or other shares of capital stock of
the Company from time to time issuable upon exercise of this Warrant. All such
shares shall be duly authorized and, when issued upon such exercise in
accordance with the terms of this Warrant, shall be validly issued, fully paid
and nonassessable, free and clear of all liens, security interests, charges and
other encumbrances or restrictions on sale (other than as provided in the
Company's articles of incorporation and any restrictions on sale set forth
herein or pursuant to applicable federal and state securities laws) and free and
clear of all preemptive rights.

          Section 4.  Fractional Interest. The Company will not issue a
                      -------------------
fractional share of Common Stock upon exercise of a Warrant. Instead, the
Company will deliver its check for the Fair Market Value of such fraction of a
share, rounded to the nearest cent.

          Section 5.  Assignment or Loss of Warrant.
                      -----------------------------

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          (1)  Except as otherwise provided herein, the Holder of this Warrant
shall not be entitled, without obtaining the consent of the Company, to assign
its interest in this Warrant in whole or in part to any person or persons;
provided, however, that this warrant may be assigned to affiliates, (including
distributions or transfers made to general or limited partners of a Holder) in
compliance with the provisions of Section 8. Subject to the provisions of
Section 8, and the obtaining of such consent of the Company, where required,
upon surrender of this Warrant to the Company or at the office of its stock
transfer agent or warrant agent, with the Assignment Form annexed hereto duly
executed and funds sufficient to pay any transfer tax, the Company shall,
without charge, execute and deliver a new Warrant or Warrants in the name of the
assignee or assignees named in such instrument of assignment and, if the Holders
entire interest is not being assigned, in the name of the Holder, and this
Warrant shall promptly be canceled.

          (2)  Upon receipt of evidence satisfactory to the Company of the loss,
theft, destruction or mutilation of this Warrant, and (in the case of loss,
theft or destruction) of indemnification satisfactory to the Company, and upon
surrender and cancellation of this Warrant, if mutilated, the Company shall
execute and deliver a new Warrant of like tenor and date.

          Section 6. Rights of the Holder. The Holder shall not, by virtue
                     --------------------
hereof, be entitled to any rights of a shareholder in the Company, either at law
or equity, and the rights of the Holder are limited to those expressed in this
Warrant. Nothing contained in this Warrant shall be construed as conferring upon
the Holder hereof the right to vote or to consent or to receive notice as a
shareholder of the Company on any matters or any rights whatsoever as a
shareholder of the Company. No dividends or interest shall be payable or accrued
in respect of this Warrant or the interest represented hereby or the Warrant
Shares purchasable hereunder until, and only to the extent that, this Warrant
shall have been exercised in accordance with its terms.

          Section 7. Adjustment of Exercise Price and Number of Shares. The
                     -------------------------------------------------
number and kind of securities purchasable upon the exercise of each Warrant and
the Exercise Price shall be subject to adjustment from time to time upon the
happening of certain events, as follows:

               (1)   Adjustment for Change in Capital Stock. If the Company:
                     --------------------------------------

                     (1) pays a dividend or makes a distribution on its Common
Stock in shares of its Common Stock;

                     (2) subdivides its outstanding shares of Common Stock into
greater number of shares;

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                     (3) combines its outstanding shares of Common Stock into a
smaller number of shares;

                     (4) makes a distribution on its Common Stock in shares of
its capital stock other than Common Stock; or

                     (5) issues by reclassification of its Common Stock any
shares of its capital stock; then the exercise right and the Exercise Price in
effect immediately prior to such action shall be adjusted so that the Holder may
receive upon exercise of the Warrants the number of shares of capital stock of
the Company which the Holder would have owned immediately following such action
if the Holder had exercised the Warrants immediately prior to such action.

      The adjustment shall become effective immediately after the record date in
the case of a dividend or distribution and immediately after the effective date
in the case of a subdivision, combination or reclassification.

                 (2) Notice of Adjustments. Whenever the Exercise Price or
                     ---------------------
number of Warrant Shares issuable upon exercise hereof shall be adjusted
pursuant to this section, the Company shall issue a certificate signed by the
secretary of the Company setting forth, in reasonable detail, the event
requiring the adjustment, the amount of the adjustment, the method by which such
adjustment was calculated and the Exercise Price and number of Warrant Shares
purchasable hereunder after giving effect to such adjustment, and shall cause a
copy of such certificate to be mailed to the holder of this Warrant.

                 (3) Deferral of Issuance or Payment. In any case in which an
                     -------------------------------
event covered by this Section 6 shall require that an adjustment in the Exercise
Price be made effective as of a record date, the Company may elect to defer
until the occurrence of such event (i) issuing to the Holder, if this Warrant is
exercised after such record date, the shares of Common Stock and other capital
stock of the Company, if any, issuable upon such exercise over and above the
shares of Common Stock or other capital stock of the Company, if any, issuable
upon such exercise on the basis of the Exercise Price in effect prior to such
adjustment, and (ii) paying to the Holder by check any amount in lieu of the
issuance of fractional shares pursuant to Section 3.

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                 (4) When No Adjustment Required. No adjustment need be made for
                     ---------------------------
a change in the par value or no par value of the Common Stock.

                 (5) Notice of Certain Actions.  In the event that:
                     -------------------------

                     (1)  the Company shall authorize the issuance to all
holders of its Common Stock of rights, warrants, options or convertible
securities to subscribe for or purchase shares of its Common Stock or of any
other subscription rights, warrants, options or convertible securities; or

                     (2)  the Company shall authorize the distribution to all
holders of its Common Stock of evidences of its indebtedness or assets (other
than dividends paid in or distributions of the Company's capital stock for which
the Exercise Price shall have been adjusted pursuant to subsection (a) of this
Section 6 or regular cash dividends or distributions payable out of earnings or
earned surplus and made in the ordinary course of business); or

                     (3)  the Company shall authorize any capital reorganization
or reclassification of the Common Stock (other than a subdivision or combination
of the outstanding Common Stock and other than a change in par value of the
Common Stock) or of any consolidation or merger to which the Company is a party
and for which approval of any stockholders of the Company is required (other
than a consolidation or merger in which the Company is the continuing
corporation and that does not result in any reclassification or change of the
Common Stock outstanding), or of the conveyance or transfer of the properties
and assets of the Company as an entirety or substantially as an entirety; or

                     (4)  the Company is the subject of a voluntary or
involuntary dissolution, liquidation or winding-up procedure;

                     (5)  the Company proposes to take any action (other than
actions of the character described in subsection (a) or (b) of this Section 6)
that would require an adjustment of the Exercise Price pursuant to this Section
6; or

                     (6)  the Company has filed a registration statement
relating to an initial public offering of its Common Stock; then the Company
shall cause to be mailed by first-class mail to the Holder, at least fifteen
(15) days prior to the applicable record or effective date hereinafter
specified, a notice stating (x) the date as of which the holders of Common Stock
of record to be entitled to receive any such rights, warrants or distributions
are to be determined, or (y) the date on which any such consolidation, merger,
conveyance, transfer, dissolution, liquidation or winding-up is expected to
become effective, and the date as of which it is expected that holders of Common
Stock of record shall be entitled to exchange their shares of Common Stock for
securities or other property, if any, deliverable upon such reorganization,
reclassification, consolidation, merger, conveyance, transfer, dissolution,

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liquidation or winding-up.

                     (6)  Common Stock Defined. Whenever reference is made in
                          --------------------
this Section 6 to the issue of shares of Common Stock, the term "Common Stock"
shall include any equity securities of any class of the Company hereinafter
authorized which shall not be limited to a fixed sum or percentage in respect of
the right of the holders thereof to participate in dividends or distributions of
assets upon the voluntary or involuntary liquidation, dissolution or winding-up
of the Company. However, subject to the provisions of Section 7 hereof, shares
issuable upon exercise hereof shall include only shares of the class designated
as Common Stock of the Company as of the date hereof or shares of any class or
classes resulting from any reclassification or reclassifications thereof or as a
result of any corporate reorganization as provided for in Section 7 hereof.

                     (7)  No Adjustment Upon Exercise of Warrants. No
                          ---------------------------------------
adjustments shall be made under any Section herein in connection with the
issuance of Warrant Shares upon exercise of the Warrants.

              Section 8.  Reclassification, Reorganization. In the event of any
                          --------------------------------
reclassification, capital reorganization or other change of outstanding shares
of Common Stock of the Company (other than a subdivision or combination of the
outstanding Common Stock and other than a change in the par value of the Common
Stock) or in the event of any consolidation or merger of the Company with or
into another corporation (other than a merger in which merger the Company is the
continuing corporation and that does not result in any reclassification, capital
reorganization or other change of outstanding shares of Common Stock of the
class issuable upon exercise of this Warrant or other transaction upon which
this Warrant terminates by its terms), the Company shall, as a condition
precedent to such transaction, cause effective provisions to be made so that the
Holder shall have the right thereafter, by exercising this Warrant, to purchase
the kind and amount of shares of stock and other securities and property
(including cash) receivable upon such reclassification, capital reorganization
and other change, consolidation or merger by a holder of the number of shares of
Common Stock that might have been received upon exercise of this Warrant
immediately prior to such reclassification, capital reorganization, change,
consolidation or merger. Any such provision shall include provisions for
adjustments in respect of such shares of stock and other securities and property
that shall be as nearly equivalent as may be practicable to the adjustments
provided for in this Warrant. The foregoing provisions of this Section 7 shall
similarly apply to successive reclassifications, capital reorganizations and
changes of shares of Common Stock and to successive consolidations and mergers.

              Section 9.  Transfer to Comply with the Securities Act of 1933.
                          --------------------------------------------------
This Warrant may not be exercised and neither this Warrant nor any of the
Warrant Shares, nor any interest in either, may be sold, assigned, pledged,
hypothecated, encumbered or

                                       9
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in any other manner transferred or disposed of, in whole or in part, except in
compliance with applicable United States federal and state securities or blue
sky laws and the terms and conditions hereof. Each Warrant shall bear a legend
in substantially the same form as the legend set forth on the first page of this
Warrant. Each certificate for Warrant Shares issued upon exercise of this
Warrant, unless at the time of exercise such Warrant Shares are acquired
pursuant to a registration statement that has been declared effective under the
Act, shall bear a legend substantially in the following form:

         THE SECURITIES REPRESENTED HEREBY HAVE NOT BEEN REGISTERED UNDER THE
         SECURITIES ACT OF 1933, AS AMENDED (THE "ACT"), OR UNDER THE SECURITIES
         LAWS OF ANY STATE. THESE SECURITIES ARE SUBJECT TO RESTRICTIONS ON
         TRANSFERABILITY AND RESALE AND MAY NOT BE TRANSFERRED OR RESOLD EXCEPT
         AS PERMITTED UNDER THE ACT AND THE APPLICABLE STATE SECURITIES LAWS,
         PURSUANT TO REGISTRATION OR EXEMPTION THEREFROM. THE ISSUER OF THESE
         SECURITIES MAY REQUIRE AN OPINION OF COUNSEL IN FORM AND SUBSTANCE
         SATISFACTORY TO THE ISSUER TO THE EFFECT THAT ANY PROPOSED TRANSFER OR
         RESALE IS IN COMPLIANCE WITH THE ACT AND ANY APPLICABLE STATE
         SECURITIES LAWS.

Any certificate for any Warrant Shares issued at any time in exchange or
substitution for any certificate for any Warrant Shares bearing such legend
(except a new certificate for any Warrant Shares issued after the acquisition of
such Warrant Shares pursuant to a registration statement that has been declared
effective under the Act) shall also bear such legend unless, in the opinion of
counsel for the Company, the Warrant Shares represented thereby need no longer
be subject to the restriction contained herein. The provision of this Section 8
shall be binding upon all subsequent holders of certificates for Warrant Shares
bearing the above legend and all subsequent holders of this Warrant, if any.

              Section 10. Modification and Waiver. This Warrant and any term
                          -----------------------
hereof may be changed, waived, discharged or terminated by an instrument in
writing signed by the Company and by the Holders of a majority of the Warrants
(on the basis of the number of Warrant Shares into which such Warrants are
exercisable) issued pursuant to the Agreement. Any amendment effected in
accordance with this Section 9 shall be binding upon each Holders of any of the
Warrants, each future Holders of all such Warrants, and the Company; provided,
however, that no special consideration or inducement may be given to any such
Holders in connection with such consent that is not given ratably to all such
Holders, and that such amendment must apply to all such

                                      10
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Holders equally and ratably in accordance with the number of shares of Common
Stock issuable upon exercise of their Warrants.

              Section 11. Notices. All notices and other communications
                          -------
required or permitted hereunder shall be in writing and shall be deemed
effectively given upon personal delivery, on the first business day following
mailing by overnight courier, or on the fifth day following mailing by
registered or certified mail, return receipt requested, postage prepaid,
addressed to the Company at the address indicated therefor in the first
paragraph of this Warrant and addressed to the Holder at 1 Procter & Gamble
Plaza, Cincinnati, Ohio 45202, Attention: Terry Overbey, Corporate Secretary or
to the Company at the address indicated therefor in the first paragraph of this
Warrant.

              Section 12. Descriptive Headings and Governing Law. The
                          --------------------------------------
description headings of the several sections and paragraphs of this Warrant are
inserted for convenience only and do not constitute a part of this Warrant. This
Warrant shall be construed and enforced in accordance with, and the rights of
the parties shall be governed by, the laws of the State of California.

              Section 13. Successors and Assigns. The terms and provisions of
                          ----------------------
this Warrant shall inure to the benefit of, and be binding upon, the Company and
the Holders hereof and their respective successors and assigns.

              Section 14. Transfer; Severability. This Warrant may not be
                          ----------------------
transferred or sold without the prior written consent of the Company. The
invalidity or unenforceability of any provision of this Warrant in any
jurisdiction shall not affect the validity or enforceability of such provision
in any other jurisdiction, or affect any other provision of this Warrant, which
shall remain in full force and effect.

                                      11
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                  IN WITNESS WHEREOF, the Company has duly caused this Warrant
to be executed by its duly authorized officer and to be dated as of May 8, 2000.


                                   PLUMTREE SOFTWARE, INC.


                                   By: /s/ JOHN KUNZE
                                      --------------------------------
                                      Name:  John Kunze
                                      Title: President and CEO

                                      12
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                                 PURCHASE FORM
                                 -------------


                                              Dated ________________, ____


[ ]  The undersigned hereby elects to exercise the within Warrant to purchase
     ___________ shares of the Common Stock of the Company (the "Shares") at a
     purchase price of Two Dollars ($2.00) per Share or an aggregate purchase
     price of _____________ Dollars ($ ) (the "Purchase Price").

[ ]  The undersigned hereby elects to convert ___________ percent ( %) of the
     value of the Warrant pursuant to the provisions of Section 1(b) of the
     Warrant.

     Pursuant to the terms of the Warrant the undersigned has delivered the
Purchase Price herewith in full in cash or by certified check or wire transfer.

                                   Very truly yours,

                                   By: _____________________________________

                                   Title:____________________________________


                                ASSIGNMENT FORM

                                              Dated ________________, ____



                  FOR VALUE RECEIVED, ___________________________ hereby sells,
assigns, and transfers unto ______________________________ (the "Assignee"),
                             (please type or print in block letters)

________________________________________________________________________________
                               (insert address)

its right to purchase up to ____ shares of Common Stock represented by this
Warrant and does hereby irrevocably constitute and appoint ____________________
as its attorney-in-fact, to transfer the same on the books of the Company, with
full power of

                                      13
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substitution in the premises.

                                                     (Signature)

                                      14


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