<PAGE>
Exhibit 4.4
BOTTOMLINE TECHNOLOGIES (de), INC.
STOCK PURCHASE AGREEMENT
This STOCK PURCHASE AGREEMENT is dated as of the 9th day of June, 2000 by
and among Bottomline Technologies (de), Inc., a Delaware corporation (the
"Company"), and Nevada Bond Investment Corp. II, a Nevada corporation (the
"Purchaser").
WHEREAS, the Company desires to issue and sell to the Purchaser pursuant to
this Agreement 307,882 shares (the "Shares") of the authorized but unissued
shares of common stock, $0.001 par value per share, of the Company (the "Common
Stock") and a warrant (the "Warrant") to purchase 307,882 shares (the "Warrant
Shares") of the Common Stock of the Company (the Shares, Warrant and Warrant
Shares are collectively referred to as the "Securities"); and
WHEREAS, the Purchaser wishes to purchase the Shares and the Warrant on the
terms and subject to the conditions set forth in this Agreement.
NOW THEREFORE, in consideration of the mutual agreements, representations,
warranties and covenants herein contained, the parties hereto agree as follows:
1. Definitions. As used in this Agreement, the following terms shall have
-----------
the following respective meanings:
(a) "Company SEC Reports" means all reports filed by the Company
-------------------
under Section 13 of the Securities Exchange Act of 1934, as amended, with the
Securities and Exchange Commission.
(b) "Exchange Act" means the Securities Exchange Act of 1934, as
------------
amended, and all of the rules and regulations promulgated thereunder.
(c) "Investor Rights Agreement" shall mean that certain Investor
-------------------------
Rights Agreement, dated as of the date hereof, among the Company and the
Purchaser.
(d) "SEC" shall mean the Securities and Exchange Commission.
---
(e) "Securities Act" shall mean the Securities Act of 1933, as
--------------
amended, and all of the rules and regulations promulgated thereunder.
<PAGE>
2. Purchase and Sale of Shares and Warrant.
---------------------------------------
2.1 Purchase and Sale. Subject to and upon the terms and conditions
-----------------
set forth in this Agreement, the Company agrees to issue and sell to the
Purchaser, and the Purchaser agrees to purchase from the Company, at Closing (as
defined below), the Shares and the Warrant to purchase the Warrant Shares at an
exercise price of $38.00 per Warrant Share. The aggregate purchase price for the
Shares and the Warrant shall be $10,000,000. The number of Shares and the number
of Warrant Shares shall each be equal to (i) 10,000,000 divided by (ii) the
number equal to the average of the last reported sale price per share of the
Company's Common Stock on the Nasdaq National Market ("NNM") for the twenty
trading days preceding the Closing Date (as defined below).
2.2 Closing. The closing of the transactions contemplated under this
-------
Agreement (the "Closing") shall take place at the office of Hale and Dorr LLP,
60 State Street, Boston, Massachusetts 02109 at 11:00 a.m. (Boston time) on June
9, 2000 or such other time or maybe mutually agreed upon by the Company and the
Purchaser (the "Closing Date"). At the Closing, the Company will deliver to the
Purchaser (i) a stock certificate representing the Shares and (ii) the Warrant,
each registered in the name of the Purchaser (or in such nominee or custodial
name as shall be specified by such purchaser), against payment of the purchase
price therefor by wire transfer of immediately available funds to such account
or accounts as the Company shall designate in writing.
3. Representations and Warranties of the Company. The Company hereby
---------------------------------------------
represents and warrants to the Purchaser as follows.
3.1 Incorporation. The Company is a corporation duly organized,
-------------
validly existing and in good standing under the laws of the State of Delaware
and is qualified to do business in each jurisdiction in which the character of
its properties or the nature of its business requires such qualification, except
where the failure to so qualify would not have a material adverse effect upon
the Company. The Company has all requisite corporate power and authority to
carry on its business as now conducted.
3.2 Capitalization. The authorized capital stock of the Company
--------------
consists of 50,000,000 shares of Common Stock and 4,000,000 shares of preferred
stock, par value $0.001 per share, of the Company (the "Preferred Stock"). As of
May 31, 2000, (i) 10,881,576 shares of Common Stock were issued and outstanding,
all of which were validly issued, fully paid, nonassessable and free of all
preemptive rights, (ii) no shares of Common Stock were held by the Company in
its treasury and (iii) no shares of Preferred Stock were issued and outstanding.
3.3 Authorization. All corporate action on the part of the Company,
-------------
its officers, directors and stockholders necessary for the authorization,
execution, delivery
2
<PAGE>
and performance of this Agreement and the Investor Rights Agreement and the
consummation of the transactions contemplated herein and therein has been taken.
When executed and delivered by the Company, each of this Agreement and the
Investor Rights Agreement shall constitute the legal, valid and binding
obligation of the Company, enforceable against the Company in accordance with
its terms, except as rights to indemnity and contribution may be limited by
state or federal securities laws or the public policy underlying such laws, and
except as may be limited by bankruptcy, insolvency, reorganization or other laws
affecting creditors' rights generally and by general equitable principles. The
Company has all requisite corporate power to enter into this Agreement and the
Investor Rights Agreement and to carry out and perform its obligations under the
terms of this Agreement and the Investor Rights Agreement.
3.4 Valid Issuance of the Shares and Warrant Shares. The Shares being
-----------------------------------------------
purchased by the Purchaser hereunder will, upon issuance pursuant to the terms
hereof, and the Warrant Shares will, upon exercise of, and in accordance with
the terms of, the Warrant, be duly authorized, validly issued, fully paid and
nonassessable.
3.5 Reports and Financial Statements. The Company has previously made
--------------------------------
available to the Purchaser complete and accurate copies, as amended or
supplemented, of the Company SEC Reports. As of their respective dates, the
Company SEC Reports did not contain any untrue statement of a material fact or
omit to state a material fact required to be stated therein as necessary to make
the statements therein, in light of the circumstances in which they were made,
not misleading. The audited financial statements and unaudited interim
financial statements of the Company included in the Company SEC Reports, as of
their respective dates, (a) complied as to form in all material respects with
applicable accounting requirements and the published rules and regulations of
the SEC with respect thereto, (b) were prepared in accordance with generally
accepted accounting principles applied on a consistent basis throughout the
periods covered thereby (except as may be indicated therein or in the notes
thereto, and in the case or quarterly financial statements, as permitted by Form
10-Q under the Exchange Act), (c) fairly represented the consolidated financial
condition, results of operations and cash flows of the Company as of the
respective dates and for the periods referred to therein or (d) are consistent
with the books and records of the Company.
3.6 Consents. All consents, approvals, orders and authorizations required
--------
on the part of the Company in connection with the execution, delivery or
performance of this Agreement and the Investor Rights Agreement and the
consummation of the transactions contemplated herein and therein have been
obtained and will be effective as of the Closing Date, other than such filings
required to be made after the Closing under applicable federal and state
securities laws and the registration statement contemplated by the Investor
Rights Agreement.
3.7 No Conflict. The execution and delivery of this Agreement and the
-----------
Investor Rights Agreement by the Company and the consummation of the
transactions
3
<PAGE>
contemplated hereby and thereby will not conflict with or result in any
violation of or default (with or without notice or lapse of time, or both)
under, or give rise to a right of termination, cancellation or acceleration of
any obligation or to a loss of a benefit under (a) any provision of the
Certificate of Incorporation or Bylaws of the Company or (b) any agreement or
instrument, permit, franchise, license, judgment, order, statute, law,
ordinance, rule or regulations, applicable to the Company or its properties or
assets other than, in the case of (b) above, any violation, default, right of
termination, cancellation, acceleration or loss of benefits the occurrence of
which would not reasonably be likely to have a material adverse effect on the
assets, business, financial conditions or results of operations of the Company.
3.8 Brokers or Finders. The Company has not incurred, and shall not
------------------
incur, directly or indirectly, any liability for any brokerage or finders' fees
or agents' commissions or any similar charges in connection with this Agreement
or any transaction contemplated hereby.
3.9 Nasdaq National Market. The Common Stock is listed on the Nasdaq
----------------------
National Market, and there are no proceedings to revoke or suspend such listing.
3.10 Absence of Litigation. As of the date hereof, there is no
---------------------
action, suit or proceeding or, to the Company's knowledge, any investigation,
pending or, to the Company's knowledge, threatened by or before any governmental
body against the Company and in which an unfavorable outcome, ruling or finding
in any said matter, or for all matters taken as a whole, would reasonably be
expected to have a material adverse effect on the Company. The foregoing
includes, without limitation, any such action, suit, proceeding or investigation
that questions this Agreement or the Investor Rights Agreement or the right of
the Company to execute, deliver and perform under same.
3.11 Absence of Certain Changes or Events. As of the date hereof,
------------------------------------
there has been no material adverse change in the business, financial condition,
or results of operations of the Company, other than changes occurring in the
ordinary course of business (which changes have not, individually or in the
aggregate, had a material adverse effect on the Company) since March 31, 2000,
the date of the balance sheets included in the Company's Form 10-Q for the
quarterly period ending March 31, 2000, it being acknowledged that the Company
anticipates that it will recognize certain non-cash expenses for accounting
purposes in connection with certain acquisition and capital transactions that
have occurred since March 31, 2000.
4. Representations and Warranties of the Purchaser. The Purchaser hereby
-----------------------------------------------
represents and warrants to the Company as follows:
4.1 Authorization. All action on the part of the Purchaser and its
-------------
officers, directors and shareholders necessary for the authorization, execution,
delivery
4
<PAGE>
and performance of this Agreement and the Investor Rights Agreement and the
consummation of the transactions contemplated herein and therein has been taken.
Each of this Agreement and the Investor Rights Agreement constitutes the legal,
valid and binding obligation of the Purchaser, enforceable against the Purchaser
in accordance with its terms, except as such may be limited by bankruptcy,
insolvency, reorganization or other laws affecting creditors' rights generally
and by general equitable principles. The Purchaser has all requisite power to
enter into each of this Agreement and the Investor Rights Agreement and to carry
out and perform its obligations under the terms of this Agreement and the
Investor Rights Agreement.
4.2 Purchase Entirely for Own Account, Etc. The Purchaser is
--------------------------------------
acquiring the Securities for its own account, and not with a view to, or for
sale in connection with, any distribution in violation of the Securities Act.
Except as contemplated by this Agreement, the Purchaser has no present
agreement, undertaking, arrangement, obligation or commitment providing for the
disposition of the Securities. The Purchaser has not been organized, reorganized
or recapitalized specifically for the purpose of investing in the Securities.
4.3 Purchaser Status, Etc. The Purchaser certifies and represents to
---------------------
the Company that at the time the Purchaser acquires any of the Securities, the
Purchaser will be an "accredited investor" as defined in Rule 501 of Regulation
D promulgated under the Securities Act. The Purchaser's financial condition is
such that it is able to bear the risk of holding the Shares for an indefinite
period of time and the risk of loss of its entire investment. The Purchaser has
been afforded the opportunity to ask questions of and receive answers from the
management of the Company concerning this investment and has sufficient
knowledge and experience in investing in companies similar to the Company in
terms of the Company's stage of development so as to be able to evaluate the
risks and merits of its investment in the Company.
4.4 Securities Not Registered. The Purchaser understands that the
-------------------------
Securities have not been registered under the Securities Act, by reason of their
issuance by the Company in transactions exempt from the registration
requirements of the Securities Act, and that the Securities must continue to be
held by the Purchaser unless a subsequent disposition thereof is registered
under the Securities Act or is exempt from such registration. The Purchaser
understands that the exemptions from registration afforded by Rule 144 (the
provisions of which are known to it) promulgated under the Securities Act depend
on the satisfaction of various conditions, and that, if applicable, Rule 144 may
afford the basis for sales only in limited amounts.
4.5 No Conflict. The execution and delivery of this Agreement and the
-----------
Investor Rights Agreement by the Purchaser and the consummation of the
transactions contemplated hereby and thereby will not conflict with or result in
any violation of or default by the Purchaser (with or without notice or lapse of
time, or both) under, or give rise to a right of termination, cancellation or
acceleration of any obligation or to a loss of a material benefit under (a) any
provision of the organizational documents of the
5
<PAGE>
Purchaser or (b) any agreement or instrument, permit, franchise, license,
judgment, order, statute, law, ordinance, rule or regulations, applicable to the
Purchaser or its respective properties or assets.
4.6 Brokers. The Purchaser has not retained, utilized or been
-------
represented by any broker or finder in connection with the transactions
contemplated by this Agreement.
4.7 Consents. All consents, approvals, orders and authorizations
--------
required on the part of the Purchaser in connection with the execution, delivery
or performance of this Agreement and the consummation of the transactions
contemplated herein have been obtained and are effective as of the Closing Date.
5. Conditions Precedent.
--------------------
5.1 Conditions to the Obligation of the Purchaser to Consummate the
---------------------------------------------------------------
Closing. The obligation of the Purchaser to consummate the Closing and to
-------
purchase and pay for the Shares and Warrant being purchased by it pursuant to
this Agreement is subject to the satisfaction of the following conditions
precedent:
(a) The representations and warranties contained herein of the
Company shall be true and correct on and as of the Closing Date with the same
force and effect as though made on and as of the Closing Date (it being
understood and agreed by the Purchaser that, in the case of any representation
and warranty of the Company contained herein (i) which is not hereinabove
qualified by application thereto of a materiality standard, such representation
and warranty need be true and correct only in all material respects in order to
satisfy as to such representation or warranty the condition precedent set forth
in the foregoing provisions of this Section 5.1(a) or (ii) which is made as of a
specific date, such representation and warranty need be true and correct only as
of such specific date in order to satisfy as to such representation and warranty
the condition precedent set forth in the foregoing provisions of this Section
5.1(a)).
(b) The Investor Rights Agreement shall have been executed and
delivered by the Company.
(c) The Company shall have performed in all material respects all
obligations and conditions herein required to be performed or observed by the
Company on or prior to the Closing Date.
(d) No proceeding challenging this Agreement or the transactions
contemplated hereby, or seeking to prohibit, alter, prevent or materially delay
the Closing, shall have been instituted before any court, arbitrator or
governmental body, agency or official and shall be pending.
6
<PAGE>
(e) The purchase of and payment for the Shares and the Warrant by the
Purchaser shall not be prohibited by any law or governmental order or
regulation.
(f) All instruments and corporate proceedings in connection with the
transactions contemplated by this Agreement to be consummated at the Closing
shall be satisfactory in form and substance to the Purchaser, and the Purchaser
shall have received copies (executed or certified, as may be appropriate) of all
documents which the Purchaser may have reasonably requested in connection with
such transactions.
5.2 Conditions to the Obligation of the Company to Consummate the
-------------------------------------------------------------
Closing. The obligation of the Company to consummate the Closing and to issue
-------
and sell to the Purchaser the Shares and the Warrant to be purchased by it at
the Closing is subject to the satisfaction of the following conditions
precedent:
(a) The representations and warranties contained herein of the
Purchaser shall be true and correct on and as of the Closing Date with the same
force and effect as though made on and as of the Closing Date (it being
understood and agreed by the Company that, in the case of any representation and
warranty of the Purchaser contained herein which is not hereinabove qualified by
application thereto of a materiality standard, such representation and warranty
need be true and correct only in all material respects in order to satisfy as to
such representation or warranty the condition precedent set forth in the
foregoing provisions of this Section 5.2(a)).
(b) The Investor Rights Agreement shall have been executed and
delivered by the Purchaser.
(c) The Purchaser shall have performed in all material respects all
obligations and conditions herein required to be performed or observed by the
Purchaser on or prior to the Closing Date.
(d) No proceeding challenging this Agreement or the transactions
contemplated hereby, or seeking to prohibit, alter, prevent or materially delay
the Closing, shall have been instituted before any court, arbitrator or
governmental body, agency or official and shall be pending.
(e) The sale of the Shares and the Warrant by the Company shall not
be prohibited by any law or governmental order or regulation.
(f) All instruments and corporate proceedings in connection with the
transactions contemplated by this Agreement to be consummated at the Closing
shall be satisfactory in form and substance to the Company, and the Company
shall have received counterpart originals, or certified or other copies of all
documents, including without limitation records of corporate or other
proceedings, which it may have reasonably requested in connection therewith.
6. Transfer, Legends.
-----------------
7
<PAGE>
6.1 Securities Law Transfer Restrictions. The Purchaser shall not
------------------------------------
sell, assign, pledge, transfer or otherwise dispose of or encumber any of the
Securities, except (i) pursuant to an effective registration statement under the
Securities Act or (ii) pursuant to an available exemption from registration
under the Securities Act and applicable state securities laws and, if requested
by the Company, upon delivery by the Purchaser of an opinion of counsel
reasonably satisfactory to the Company (it be acknowledged that Kirkpatrick &
Lockhart LLP shall be deemed satisfactory) to the effect that the proposed
transfer is exempt from registration under the Securities Act and applicable
state securities laws; provided that no such opinion shall be required for any
--------
transfer of Shares that is exempt from such registration under Rule 144(k) under
the Securities Act. Any transfer or purported transfer of the Shares or warrants
in violation of this Section 6.1 shall be voidable by the Company. The Company
shall not register any transfer of the Shares or Warrants in violation of this
Section 6.1. The Company may, and may instruct any transfer agent for the
Company to, place such stop transfer orders as may be required on the transfer
books of the Company in order to ensure compliance with the provisions of this
Section 6.1.
6.2 Legends. Certificates representing the Shares and Warrant Shares
-------
shall be endorsed with the legends set forth below, and the Purchaser covenants
that, except to the extent such restrictions are waived by the Company, it shall
not transfer any shares represented by any such certificate without complying
with the restrictions on transfer described in this Agreement and the legends
endorsed on such certificates:
"THE SHARES REPRESENTED BY THIS CERTIFICATE HAVE NOT BEEN REGISTERED UNDER THE
SECURITIES ACT OF 1933 AND MAY NOT BE OFFERED, SOLD, ASSIGNED, PLEDGED,
TRANSFERRED OR OTHERWISE DISPOSED OF IN THE ABSENCE OF AN EFFECTIVE REGISTRATION
STATEMENT UNDER SAID ACT OR PURSUANT TO AN AVAILABLE EXEMPTION FROM REGISTRATION
UNDER SAID ACT AND, IF REQUESTED BY THE COMPANY, UPON DELIVERY OF AN OPINION OF
COUNSEL REASONABLY SATISFACTORY TO THE COMPANY THAT THE PROPOSED TRANSFER IS
EXEMPT FROM SAID ACT."
The Company shall cause the legend to be removed upon the registration of the
Shares and the Warrant Shares pursuant to the Investor Rights Agreement.
8
<PAGE>
7. Miscellaneous Provisions.
------------------------
7.1 Further Assurances. Both parties agree to cooperate fully with
------------------
the other party and to execute such further instruments, documents and
agreements and to give such further written assurances, as may be reasonably
requested by the other party to better evidence and reflect the transactions
described herein and contemplated hereby, and to carry into effect the intents
and purposes of this Agreement.
7.2 Rights Cumulative. Each and all of the various rights, powers and
-----------------
remedies of the parties shall be considered to be cumulative with and in
addition to any other rights, powers and remedies which such parties may have at
law or in equity in the event of the breach of any of the terms of this
Agreement. The exercise or partial exercise of any right, power or remedy shall
neither constitute the exclusive election thereof nor the waiver of any other
right, power or remedy available to such party.
7.3 Pronouns. All pronouns or any variation thereof shall be deemed
--------
to refer to the masculine, feminine or neuter, singular or plural, as the
identity of the person, persons, entity or entities may require.
7.4 Notices.
-------
(a) Any notices, reports or other correspondence (hereinafter
collectively referred to as "correspondence") required or permitted to be given
hereunder shall be sent by postage prepaid first class mail, courier or fax or
delivered by hand to the party to whom such correspondence is required or
permitted to be given hereunder. The date of giving any notice shall be the date
of its actual receipt.
(b) All correspondence to the Company shall be addressed as follows:
Bottomline Technologies (de), Inc.
155 Fleet Street
Portsmouth, NH 03801
Attn: Robert A. Eberle
Executive Vice President & CFO
With a copy to:
Hale and Dorr LLP
60 State Street
Boston, MA 02109
Attn: John A. Burgess, Esq.
(c) All correspondence to the Purchaser shall be addressed as
follows:
Nevada Bond Investment Corp. II
9
<PAGE>
c/o United Technologies Corporation
United Technologies Building
Hartford, CT 06101
Attn: Mr. Lawrence V. Mowell
Vice President, NBIC
With a copy to:
Kirkpatrick & Lockhart LLP
1500 Oliver Building
Pittsburgh, PA 15222
Attn: Robert P. Zinn, Esq.
(d) Either party may change the address to which correspondence to it
is to be addressed by notification as provided for herein.
7.5 Captions. The captions and paragraph headings of this Agreement
--------
are solely for the convenience of reference and shall not affect its
interpretation.
7.6 Severability. Should any part or provision of this Agreement be
------------
held unenforceable or in conflict with the applicable laws or regulations of any
jurisdiction, the invalid or unenforceable part or provisions shall be replaced
with a provision which accomplishes, to the extent possible, the original
business purpose of such part or provision in a valid and enforceable manner,
and the remainder of this Agreement shall remain binding upon the parties
hereto.
7.7 Governing Law; Injunctive Relief.
--------------------------------
(a) This Agreement shall be governed by and construed in accordance
with the internal and substantive laws of Delaware and without regard to any
conflicts of laws concepts which would apply the substantive law of some other
jurisdiction.
(b) Both parties hereto acknowledge and agree that damages will not
be an adequate remedy for any material breach or violation of this Agreement if
such material breach or violation would cause immediate and irreparable harm (an
"Irreparable Breach"). Accordingly, in the event of a threatened or ongoing
Irreparable Breach, both parties hereto shall be entitled to seek, in any state
or federal court in Delaware, equitable relief of a kind appropriate in light of
the nature of the ongoing or threatened Irreparable Breach, which relief may
include, without limitation, specific performance or injunctive relief;
provided, however, that if the party bringing such action is unsuccessful in
obtaining the relief sought, the moving party shall pay the non-moving party's
reasonable costs, including attorney's fees, incurred in connection with
defending such action. Such remedies shall not be the parties' exclusive
remedies, but shall be in addition to all other remedies provided in this
Agreement.
10
<PAGE>
7.8 Waiver. No waiver of any term, provision or condition of this
------
Agreement, whether by conduct or otherwise, in any one or more instances, shall
be deemed to be, or be construed as, a further or continuing waiver of any such
term, provision or condition or as a waiver of any other term, provision or
condition of this Agreement.
7.9 Expenses. Each party will bear its own costs and expenses in
--------
connection with this Agreement.
7.10 Assignment. The rights and obligations of the parties hereto
----------
shall inure to the benefit of and shall be binding upon the authorized
successors and permitted assigns of each party. Neither party may assign its
rights or obligations under this Agreement or designate another person (i) to
perform all or part of its obligations under this Agreement or (ii) to have all
or part of its rights and benefits under this Agreement, in each case without
the prior written consent of the other party. In the event of any assignment in
accordance with the terms of this Agreement, the assignee shall specifically
assume and be bound by the provisions of the Agreement by executing and agreeing
to an assumption agreement reasonably acceptable to the other party.
7.11 Survival. The respective representations and warranties given by
--------
the parties hereto, and the other covenants and agreements contained herein,
shall survive the Closing Date and the consummation of the transactions
contemplated herein for a period of two years.
7.12 Entire Agreement. This Agreement and the Investor Rights
----------------
Agreement constitute the entire agreement between the parties hereto respecting
the subject matter hereof and supersedes all prior agreements, negotiations,
understandings, representations and statements respecting the subject matter
hereof, whether written or oral. No modification, alteration, waiver or change
in any of the terms of this Agreement shall be valid or binding upon the parties
hereto unless made in writing and duly executed by the Company and the
Purchaser.
11
<PAGE>
IN WITNESS WHEREOF, the parties hereto have executed this Agreement under
seal as of the day and year first above written.
BOTTOMLINE TECHNOLOGIES (de), INC.
By: /s/ Robert Eberle
------------------------------
Name: Robert Eberle
Title: Exec VP & CFO
NEVADA BOND INVESTMENT CORP. II
By: /s/ L. V. Mowell
------------------------------
Name: L.V. Mowell
Title: Vice President
12
