Exhibit 10.1


 


SERIES B PREFERRED STOCK PURCHASE AGREEMENT


 


This SERIES B PREFERRED STOCK PURCHASE AGREEMENT (the “Agreement”), is made as of November 9, 2005, by and between
Intraware, Inc., a Delaware corporation (the “Company”),
and Digital River, Inc., a Delaware corporation (“Digital
River”).


 


WHEREAS, the
Company and Digital River are executing and delivering this Agreement in
reliance upon the exemption from securities registration afforded by
Rule 506 of Regulation D (“Regulation D”)
as promulgated by the U.S. Securities and Exchange Commission (the “SEC”) under the Securities Act of 1933, as amended (the “Securities Act”);


 


WHEREAS,
Digital River wishes to purchase, upon the terms and conditions stated in this
Agreement, 1,000 shares of Series B Preferred Stock, par value $0.0001 per
share, of the Company (the “Shares”) which
are convertible into shares of Common Stock of the Company (the “Conversion Shares”); and


 


WHEREAS,
contemporaneously with the execution and delivery of this Agreement, the parties
hereto are executing and delivering an Investor Rights Agreement substantially
in the form attached hereto as Exhibit A (the “Investor
Rights Agreement”) and a Standstill and Stock Restriction Agreement
substantially in the form attached hereto as Exhibit B (the “Standstill Agreement”).


 


NOW
THEREFORE, in consideration of the covenants and promises set forth herein, and
for other good and valuable consideration, the receipt and sufficiency of which
is hereby acknowledged, the parties hereby agree as follows:


 


ARTICLE I


 


PURCHASE AND SALE OF SHARES


 


1.1           Purchase
of the Shares.  Subject to the terms
and conditions of this Agreement, Digital River agrees to purchase at the
Closing (as defined below) and the Company agrees to sell and issue to Digital
River, the Shares, at a purchase price of $6,000.00 per share, for an aggregate
purchase price of $6,000,000.00 (the “Purchase Price”).


 


1.2           Closing
Date.  The purchase and sale of the
Shares shall take place at the offices of Wilson Sonsini Goodrich &
Rosati, Professional Corporation, 650 Page Mill Road, Palo Alto,
California, at 10:00 a.m. Pacific time, on November 10, 2005, or at such other
time and place as the Company and Digital River shall agree upon, orally or in
writing (the “Closing”).  The date and time of the Closing is hereafter
referred to as the “Closing Date.”


 


1.3           Form of
Payment.  On the Closing Date,
(i) Digital River shall pay the aggregate Purchase Price to the Company
for the Shares to be issued and sold to Digital River at the Closing, by wire
transfer of immediately available funds in accordance with the Company’s
written wire instructions, and (ii) the Company shall deliver to the
Company’s transfer agent instructions to issue a stock certificates
representing such number of the Shares (the “Stock
Certificate”).


 





















 


ARTICLE II


 


DIGITAL RIVER’S REPRESENTATIONS
AND WARRANTIES


 


Digital River
represents and warrants to the Company that:


 


2.1           Investment
Purpose.  Digital River is acquiring
the Shares for its own account for investment only and not with a view towards,
or for resale in connection with, the public sale or distribution thereof,
except pursuant to sales registered or exempted under the Securities Act.


 


2.2           Accredited
Investor Status.  Digital River is an
“accredited investor” as that term is defined in Rule 501(a) of
Regulation D.


 


2.3           Reliance
on Exemptions.  Digital River
understands that the Shares are being offered and sold to it in reliance on
specific exemptions from the registration requirements of United States federal
and state securities laws and that the Company is relying in part upon the
truth and accuracy of, and Digital River’s compliance with, the
representations, warranties, agreements, acknowledgments and understandings of
Digital River set forth herein in order to determine the availability of such
exemptions and the eligibility of Digital River to acquire the Shares.


 


2.4           Information.  Digital River and its advisors, if any, have
been furnished with all materials relating to the business, finances and
operations of the Company and materials relating to the offer and sale of the
Shares which have been requested by Digital River.  Digital River and its advisors, if any, have
been afforded the opportunity to ask questions of the Company.  Neither such inquiries nor any other due
diligence investigations conducted by Digital River or its advisors, if any, or
its representatives shall modify, amend or affect Digital River’s right to rely
on the Company’s representations and warranties contained herein.  Digital River understands that its investment
in the Shares involves a high degree of risk. 
Digital River has sought such accounting, legal and tax advice as it has
considered necessary to make an informed investment decision with respect to
its acquisition of the Shares.


 


2.5           No
Governmental Review.  Digital River
understands that no United States federal or state agency or any other
government or governmental agency has passed on or made any recommendation or
endorsement of the Shares or the fairness or suitability of the investment in
the Shares nor have such authorities passed upon or endorsed the merits of the
offering of the Shares.


 


2.6           Transfer
or Resale.  Digital River understands
that except as provided in the Investor Rights Agreement: (i) the Shares
have not been and are not being registered under the Securities Act or any
state securities laws, and may not be offered for sale, sold, assigned or
transferred, unless in accordance with the terms of the Standstill Agreement,
and additionally (A) subsequently registered thereunder, (B) Digital
River shall have delivered to the Company an opinion of counsel, in a generally
acceptable form, to the effect that such Shares to be sold, assigned or
transferred may be sold, assigned or transferred pursuant to an exemption from
such registration, or (C) Digital River provides the Company with
reasonable assurance that such Shares can be sold, assigned or transferred
pursuant to Rule 144 promulgated under the Securities Act (or a successor
rule thereto) (“Rule 144”); (ii) any
sale of the Shares made in reliance on Rule 144 may be made only in


 


2





















 


accordance with the terms of Rule 144 and
further, if Rule 144 is not applicable, any resale of the Shares under
circumstances in which the seller (or the person through whom the sale is made)
may be deemed to be an underwriter (as that term is defined in the Securities
Act) may require compliance with some other exemption under the Securities Act
or the rules and regulations of the SEC thereunder; and (iii) neither the
Company nor any other person is under any obligation to register the Shares for
resale under the Securities Act or any state securities laws or to comply with
the terms and conditions of any resale exemption thereunder.


 


2.7           Legends.  Digital River understands that the
certificates or other instruments representing the Shares, until such time as
the sale of the Shares have been registered under the Securities Act as
contemplated by the Investor Rights Agreement, the stock certificates
representing the Shares, shall bear a restrictive legend in substantially the
following form (and a stop-transfer order may be placed against transfer of
such stock certificates and warrants):


 


THE SECURITIES
REPRESENTED BY THIS CERTIFICATE HAVE NOT BEEN REGISTERED UNDER THE SECURITIES
ACT OF 1933, AS AMENDED, OR APPLICABLE STATE SECURITIES LAWS.  THE SECURITIES MAY NOT BE OFFERED FOR SALE,
SOLD, TRANSFERRED OR ASSIGNED (I) IN THE ABSENCE OF (A) AN EFFECTIVE
REGISTRATION STATEMENT FOR THE SECURITIES UNDER THE SECURITIES ACT OF 1933, AS
AMENDED, OR APPLICABLE STATE SECURITIES LAWS, OR (B) AN OPINION OF
COUNSEL, IN A GENERALLY ACCEPTABLE FORM, THAT REGISTRATION IS NOT REQUIRED
UNDER SAID ACT OR APPLICABLE STATE SECURITIES LAWS OR (II) UNLESS SOLD
PURSUANT TO RULE 144 UNDER SAID ACT.


 


The legend set
forth above shall be removed and the Company shall issue a certificate without
such legend to the holder of the Shares upon which it is stamped, if, unless
otherwise required by state securities laws, (i) such Shares are
registered for sale under the Securities Act, (ii) in connection with a
sale, assignment or other transfer, such holder provides the Company with an
opinion of counsel, in a generally acceptable form, to the effect that such
sale, assignment or transfer of the Shares may be made without registration
under the Securities Act, or (iii) such holder provides the Company with
reasonable assurance that the Shares can be sold, assigned or transferred
pursuant to Rule 144 without any restriction as to the number of
securities acquired as of a particular date that can then be immediately sold.


 


2.8           Validity;
Enforcement.  This Agreement has been
duly and validly authorized, executed and delivered on behalf of Digital River
and is a valid and binding agreement of Digital River enforceable against
Digital River in accordance with its terms, subject as to enforceability to
general principles of equity and to applicable bankruptcy, insolvency,
reorganization, moratorium, liquidation and other similar laws relating to, or
affecting generally, the enforcement of applicable creditors’ rights and
remedies.


 


3





















 


ARTICLE III


 


REPRESENTATIONS AND WARRANTIES OF
THE COMPANY.


 


The Company
represents and warrants to Digital River, except as set forth in the Schedule
of Exceptions attached hereto as Exhibit C, that:


 


3.1           Organization
and Qualification.  The Company and
its “Subsidiaries” (which for purposes of
this Agreement means any entity in which the Company, directly or indirectly,
owns capital stock or holds a majority or similar interest) are corporations
duly organized and validly existing in good standing under the laws of the
jurisdiction in which they are incorporated, and have the requisite corporate
power and authorization to own their properties and to carry on their business
as now being conducted.  Each of the
Company and its Subsidiaries is duly qualified as a foreign corporation to do
business and is in good standing in every jurisdiction in which its ownership of
property or the nature of the business conducted by it makes such qualification
necessary, except to the extent that the failure to be so qualified or be in
good standing would not have a Material Adverse Effect.  As used in this Agreement, “Material Adverse Effect” means any material adverse effect
on the business, properties, assets, operations, results of operations or
financial condition of the Company and its Subsidiaries, if any, taken as a
whole, or on the transactions contemplated hereby or by the agreements and
instruments to be entered into in connection herewith, or on the authority or
ability of the Company to perform its obligations under the Transaction
Documents (as defined below) or the Certificate of Designation (as defined
below).


 


3.2           Authorization;
Enforcement; Validity.  The Company
has the requisite corporate power and authority to enter into and perform this
Agreement, the Investor Rights Agreement and the Standstill Agreement,
(together, the “Transaction Documents”) and to
file, and perform its obligations under, the Transaction Documents, and to
issue the Shares in accordance with the terms hereof and thereof.  The execution and delivery of the Transaction
Documents by the Company and the consummation by the Company of the transactions
contemplated hereby and thereby, including without limitation the issuance of
the Shares, have been duly authorized by the Company’s Board of Directors and
no further consent or authorization is required by the Company, its Board of
Directors or its stockholders.  The
Transaction Documents of even date herewith have been duly executed and
delivered by the Company, and constitute the valid and binding obligations of
the Company enforceable against the Company in accordance with their terms,
except as such enforceability may be limited by general principles of equity or
applicable bankruptcy, insolvency, reorganization, moratorium, liquidation or
similar laws relating to, or affecting generally, the enforcement of creditors’
rights and remedies.


 


3.3           Issuance
of Securities.  The Shares are duly
authorized and, upon issuance at the Closing, shall be (i) validly issued,
fully paid and non-assessable, (ii) free from all taxes, liens and charges
with respect to the issue thereof and (iii) entitled to the rights and
preferences set forth in the Company’s form of Certificate of Designations,
Preferences and Rights of Series B Preferred Stock attached hereto as Exhibit D
(the “Certificate of Designations”).  At least 1,000,000 shares of Common Stock
have been duly authorized and reserved for issuance upon conversion of the
Shares.  Upon conversion or exercise in
accordance with the Certificate of Designations, the Conversion Shares will be
validly issued, fully paid and nonassessable and free from all taxes, liens and
charges


 


4





















 


with respect to the issue thereof, with the holders
being entitled to all rights accorded to a holder of Common Stock.  The issuance by the Company of the Shares is
exempt from registration under the Securities Act.


 


3.4           No
Conflicts.  The execution, delivery
and performance of the Transaction Documents by the Company, the performance by
the Company of its obligations under the Certificate of Designations and the
consummation by the Company of the transactions contemplated hereby and thereby
(including, without limitation, the reservation for issuance and issuance of
the Conversion Shares) will not (i) result in a violation of the Company’s
certificate of incorporation, any certificate of designations, preferences and
rights of any outstanding series of preferred stock of the Company or the
Company’s bylaws or (ii) conflict with, or constitute a default (or an
event which with notice or lapse of time or both would become a default) under,
or give to others any rights of termination, amendment, acceleration or
cancellation of, any material agreement filed as an exhibit to any of the
Company’s SEC Documents (as defined below), or (iii) result in a violation
of any law, rule, regulation, order, judgment or decree (including federal and
state securities laws and regulations and the rules and regulations of The
Nasdaq Stock Market, Inc. (“Nasdaq”))
applicable to the Company or any of its Subsidiaries or by which any property
or asset of the Company or any of its Subsidiaries is bound or affected.


 


3.5           Consents.  Except for the filing of (i) the Registration
Statement (as defined in the Investor Rights Agreement) with the SEC, (ii) the
Certificate of Designations with the State of Delaware and (iii) the Form D
with the SEC, the Company is not required to obtain any consent, authorization
or order of, or make any filing or registration with, any court or governmental
agency or any regulatory or self-regulatory agency in order for it to execute,
deliver or perform any of its obligations under or contemplated by the
Transaction Documents.  All consents,
authorizations, orders, filings and registrations which the Company is required
to obtain pursuant to the preceding sentence have been obtained or effected on
or prior to the date hereof.  The Company
and its Subsidiaries are unaware of any facts or circumstances which might
prevent the Company from obtaining or effecting any of the foregoing.


 


3.6           No
General Solicitation; Placement Agent. 
Neither the Company, nor any of its affiliates, nor any person acting on
its or their behalf, has engaged in any form of general solicitation or general
advertising (within the meaning of Regulation D under the Securities Act)
in connection with the offer or sale of the Shares.  The Company acknowledges that it has not
engaged a placement agent in connection with the sale of the Shares.


 


3.7           No
Integrated Offering.  None of the
Company, its Subsidiaries, any of their affiliates, and any person acting on
their behalf has, directly or indirectly, made any offers or sales of any
security or solicited any offers to buy any security, under circumstances that
would require registration of any of the Shares under the Securities Act or
cause this offering of the Shares to be integrated with prior offerings by the
Company for purposes of the Securities Act or any applicable stockholder
approval provisions, including, without limitation, under the rules and
regulations of any exchange or automated quotation system on which any of the
securities of the Company are listed or designated.  None of the Company, its Subsidiaries, their
affiliates and any person acting on their behalf will take any action or steps
referred to in the preceding sentence that would require


 


5





















 


registration of any of the Shares under the Securities
Act or cause the offering of the Shares to be integrated with other offerings.


 


3.8           Application
of Takeover Protections; Rights Agreement. 
The Company and its Board of Directors have taken all necessary action,
if any, in order to render inapplicable any control share acquisition, business
combination, poison pill (including any distribution under a rights agreement)
or other similar anti-takeover provision under the Company’s certificate of
incorporation or the laws of the state of its incorporation which is or could
become applicable to Digital River as a result of the transactions contemplated
by this Agreement, including, without limitation, the Company’s issuance of the
Shares (or upon conversion or exercise, the Conversion Shares) and Digital
River’s ownership of the Shares or the Conversion Shares.


 


3.9           SEC
Documents; Financial Statements. 
Since July 1, 2004, the Company has filed all reports, schedules, forms,
statements and other documents required to be filed by it with the SEC pursuant
to the reporting requirements of the Securities Exchange Act of 1934, as
amended (the “Exchange Act”) (all of the
foregoing filed prior to the date hereof and all exhibits included therein and
financial statements and schedules thereto and documents incorporated by
reference therein being hereinafter referred to as the “SEC
Documents”).  The Company has
made available to Digital River or its respective representatives copies of the
SEC Documents.  As of their respective
dates, the SEC Documents complied in all material respects with the
requirements of the Exchange Act and the rules and regulations of the SEC
promulgated thereunder applicable to the SEC Documents, and none of the SEC
Documents, at the time they were filed with the SEC, contained any untrue
statement of a material fact or omitted to state a material fact required to be
stated therein or necessary in order to make the statements therein, in light
of the circumstances under which they were made, not misleading.  As of their respective dates, the financial
statements of the Company included in the SEC Documents complied as to form in
all material respects with applicable accounting requirements and the published
rules and regulations of the SEC with respect thereto.  Such financial statements have been prepared
in accordance with generally accepted accounting principles, consistently
applied, during the periods involved (except (i) as may be otherwise
indicated in such financial statements or the notes thereto, or (ii) in
the case of unaudited interim statements, to the extent they may exclude
footnotes or may be condensed or summary statements) and fairly present in all
material respects the financial position of the Company as of the dates thereof
and the results of its operations and cash flows for the periods then ended
(subject, in the case of unaudited statements, to normal year-end audit
adjustments).


 


3.10         Conduct
of Business; Regulatory Permits. 
Neither the Company nor any of its Subsidiaries is in violation of any
judgment, decree or order or any statute, ordinance, rule or regulation
applicable to the Company or its Subsidiaries, and neither the Company nor any
of its Subsidiaries will conduct its business in violation of any of the
foregoing, except for possible violations which would not, individually or in
the aggregate, have a Material Adverse Effect. 
The Company and its Subsidiaries possess all certificates,
authorizations and permits issued by the appropriate federal, state or foreign
regulatory authorities necessary to conduct their respective businesses, except
where the failure to possess such certificates, authorizations or permits would
not have, individually or in the aggregate, a Material Adverse Effect, and neither
the Company nor any such Subsidiary has received any notice of proceedings
relating to the revocation or modification of any such certificate,
authorization or permit.


 


6





















 


3.11         Foreign
Corrupt Practices.  Neither the
Company, nor any of its Subsidiaries, nor any director, officer, agent,
employee or other person acting on behalf of the Company or any of its
Subsidiaries has, in the course of its actions for, or on behalf of, the
Company, used any corporate funds for any unlawful contribution, gift,
entertainment or other unlawful expenses relating to political activity; made
any direct or indirect unlawful payment to any foreign or domestic government
official or employee from corporate funds; violated or is in violation of any
provision of the U.S. Foreign Corrupt Practices Act of 1977, as amended; or
made any unlawful bribe, rebate, payoff, influence payment, kickback or other
unlawful payment to any foreign or domestic government official or employee.


 


3.12         Absence
of Litigation.  There is no material
action, suit, proceeding, inquiry or investigation before or by Nasdaq, any
court, public board, government agency, self-regulatory organization or body
pending against the Company, the Common Stock or any of the Company’s
Subsidiaries or any of the Company’s or the Company’s Subsidiaries’ officers or
directors in their capacities as such. 
There is no action, suit, proceeding or investigation pending, or to the
Company’s knowledge, threatened against the Company that questions the validity
of the Transaction Documents or the right of the Company to enter such
agreements or consummate the transactions contemplated thereby.


 


3.13         Tax
Status.  The Company and each of its
Subsidiaries has made or filed all federal and state income and all other tax
returns, reports and declarations required by any jurisdiction to which it is
subject, and has paid all taxes and other governmental assessments and charges
that are material in amount, shown or determined to be due on such returns,
reports and declarations, except those being contested in good faith and has
set aside on its books provision reasonably adequate for the payment of all
taxes for periods subsequent to the periods to which such returns, reports or
declarations apply.  There are no unpaid
taxes in any material amount claimed to be due by the taxing authority of any
jurisdiction, and the officers of the Company know of no basis for any such
claim.  There are no ongoing or pending
tax audits by any taxing authority against the Company.


 


ARTICLE IV


 


COVENANTS.


 


4.1           Form D
and Blue Sky.  The Company agrees to
file a Form D with respect to the Shares as required under
Regulation D and to provide upon request a copy thereof to Digital River
promptly after such filing.  The Company
shall, on or before the Closing Date, take such action as the Company shall
reasonably determine is necessary in order to obtain an exemption for or to
qualify the Shares for sale to Digital River pursuant to this Agreement under
applicable securities or “Blue Sky” laws of the states of the United States,
and shall provide evidence of any such action so taken to Digital River on or
prior to the Closing Date.  The Company
shall make all filings and reports relating to the offer and sale of the
Securities required under applicable securities or “Blue Sky” laws of the
states of the United States following the Closing Date.


 


4.2           Expenses;
Fees.  Each party shall each pay their own expenses in
connection with the transactions contemplated by this Agreement.


 


7





















 


ARTICLE V


 


CONDITIONS TO THE COMPANY’S
OBLIGATION TO SELL.


 


The obligation of the Company
hereunder to issue and sell the Shares to Digital River at the Closing is
subject to the satisfaction, at or before the Closing Date, of each of the
following conditions, provided that these conditions are for the Company’s sole
benefit and may be waived by the Company at any time in its sole discretion by
providing Digital River with prior written notice thereof:


 


5.1           Digital
River shall have executed and delivered to the Company each of the Transaction
Documents.


 


5.2           Digital
River shall have delivered to the Company the Purchase Price for the Shares
being purchased by Digital River at the Closing by wire transfer of immediately
available funds pursuant to the wire instructions provided by the Company.


 


5.3           The
representations and warranties of Digital River shall be true and correct in
all material respects as of the date when made and as of the Closing Date as
though made at that time, and Digital River shall have performed, satisfied and
complied in all material respects with the covenants, agreements and conditions
required by this Agreement to be performed, satisfied or complied with by
Digital River at or prior to the Closing Date.


 


5.4           The
Company shall have filed the Certificate of Designations with the Secretary of
State of the State of Delaware.


 


ARTICLE VI


 


CONDITIONS TO DIGITAL RIVER’S
OBLIGATION TO PURCHASE.


 


The obligation
of Digital River hereunder to purchase the Shares is subject to the
satisfaction, at or before the Closing Date, of each of the following
conditions, provided that these conditions are for Digital River’s sole benefit
and may be waived by Digital River at any time in its sole discretion by
providing the Company with prior written notice thereof:


 


6.1           The
Company shall have executed and delivered to Digital River each of the
Transaction Documents.


 


6.2           Digital
River shall have received the opinion of the Company’s counsel dated as of the
Closing Date, in substantially the form attached hereto as Exhibit E.


 


6.3           The
representations and warranties of the Company shall be true and correct as of
the date when made and as of the Closing Date as though made at that time
(except for representations and warranties that reference a specific date which
shall have been true and correct in all material respects as of such date) and
the Company shall have performed, satisfied and complied in all respects with
the covenants, agreements and conditions required by the Transaction Documents
to be performed, satisfied or complied with by the Company at or prior to the
Closing Date.


 


8





















 


6.4           The
Company shall have filed the Certificate of Designations with the Secretary of
State of the State of Delaware.


 


ARTICLE VII


 


MISCELLANEOUS


 


7.1           Governing
Law.  This Agreement shall be
governed by and construed in accordance with the laws of the State of Delaware,
regardless of the laws that might otherwise govern under applicable principles
of conflicts of laws thereof.


 


7.2           Counterparts.  This Agreement may be executed in two or more
identical counterparts, all of which shall be considered one and the same
agreement and shall become effective when counterparts have been signed by each
party and delivered to the other party; provided that a facsimile signature
shall be considered due execution and shall be binding upon the signatory
thereto with the same force and effect as if the signature were an original,
not a facsimile signature.


 


7.3           Headings.  The headings of this Agreement are for
convenience of reference and shall not form part of, or affect the
interpretation of, this Agreement.


 


7.4           Severability.  If any provision of this Agreement shall be
invalid or unenforceable in any jurisdiction, such invalidity or
unenforceability shall not affect the validity or enforceability of the
remainder of this Agreement in that jurisdiction or the validity or
enforceability of any provision of this Agreement in any other jurisdiction.


 


7.5           Entire
Agreement; Amendments.  This
Agreement supersedes all other prior oral or written agreements between Digital
River, the Company, their affiliates and persons acting on their behalf with
respect to the matters discussed herein, and this Agreement and the instruments
referenced herein, together with that certain Mutual Confidentiality Agreement
dated as of June 11, 2001 (which agreement the parties hereby acknowledge and
agree (i) is in full force and effect and has been in full force and effect at
all times since June 11, 2001, and (ii) for purposes
thereof, the term “Potential Transaction” shall be deemed
to include the investment by Digital River in the Company’s Series B Preferred
Stock and the potential strategic alliance agreement to be entered into between
the Company and Digital River) contain the entire understanding of the parties
with respect to the matters covered herein and therein and, except as
specifically set forth herein or therein, neither the Company nor Digital River
makes any representation, warranty, covenant or undertaking with respect to
such matters.  No provision of this
Agreement may be amended other than by an instrument in writing signed by the
Company and Digital River, and no provision hereof may be waived other than by
an instrument in writing signed by the party against whom enforcement is
sought.


 


7.6           Notices.  Any notices, consents, waivers or other
communications required or permitted to be given under the terms of this
Agreement must be in writing and will be deemed to have been delivered:  (i) upon receipt, when delivered
personally; (ii) upon receipt, when sent by facsimile (provided
confirmation of transmission is mechanically or electronically generated and


 


9





















 


kept on file by the sending party); or (iii) one
business day after deposit with an overnight courier service, in each case
properly addressed to the party to receive the same.  The addresses and facsimile numbers for such
communications shall be:


 


If to the
Company:


 


Intraware,
Inc.


25 Orinda Way


Orinda,
CA  94563


	
  Telephone:

  	
   

  	
  (925) 253-4500

  
	
  Facsimile:

  	
   

  	
  (925)
  253-4541

  
	
  Attention:

  	
   

  	
  President
  and Chief Executive Officer

  
	
   

  	
   

  	
  General
  Counsel

  



 


 


With a copy
to:


 


Wilson Sonsini
Goodrich & Rosati, Professional Corporation


650 Page Mill
Road


Palo Alto, CA
94304


	
  Telephone:

  	
   

  	
  (650) 493-9300

  
	
  Facsimile:

  	
   

  	
  (650) 493-6811

  
	
  Attention:

  	
   

  	
  David J.
  Segre, Esq.

  
	
   

  	
   

  	
  N. Anthony
  Jeffries, Esq.

  



 


If to Digital
River:


 


Digital River,
Inc.


9625 West 76th
Street, Suite 150


Eden Prairie,
MN  55344


	
  Telephone:

  	
   

  	
  952-253-1234

  
	
  Facsimile:

  	
   

  	
  952-253-8370

  
	
  Attention:

  	
   

  	
  Joel Ronning

  



 


With a copy
to:


 


Robins,
Kaplan, Miller & Ciresi L.L.P.


2800 LaSalle Plaza


800 LaSalle Avenue


Minneapolis, Minnesota 55402


	
  Attention:

  	
   

  	
  Kevin L.
  Crudden, Esq.

  
	
  Telephone:

  	
   

  	
  (612)
  349-8500

  
	
  Facsimile:

  	
   

  	
  (612)
  339-4181

  



 


Written
confirmation of receipt (A) given by the recipient of such notice,
consent, waiver or other communication, (B) mechanically or electronically
generated by the sender’s facsimile machine containing the time, date,
recipient facsimile number and an image of the first page of such transmission
or (C) provided by an overnight courier service shall be rebuttable
evidence of personal


 


10





















 


service, receipt by facsimile
or receipt from an overnight courier service in accordance with
clause (i), (ii) or (iii) above, respectively.


 


7.7           Successors
and Assigns.  This Agreement shall be
binding upon and inure to the benefit of the parties and their respective
successors and assigns, including any purchasers of the Shares.  The Company shall not assign this Agreement
or any rights or obligations hereunder without the prior written consent of
Digital River.  Digital River may assign
some or all of its rights hereunder without the consent of the Company,
provided, however, that any such assignment shall not release Digital River
from its obligations hereunder unless such obligations are assumed by such
assignee and the Company has consented to such assignment and assumption, which
consent shall not be unreasonably withheld.


 


7.8           No
Third Party Beneficiaries.  This
Agreement is intended for the benefit of the parties hereto and their
respective permitted successors and assigns, and is not for the benefit of, nor
may any provision hereof be enforced by, any other person.


 


7.9           Survival.  The representations and warranties of the
Company and Digital River contained in Sections 2 and 3 and the
agreements set forth this Article VII shall survive the Closing.


 


7.10         Further
Assurances.  Each party shall do and
perform, or cause to be done and performed, all such further acts and things,
and shall execute and deliver all such other agreements, certificates,
instruments and documents, as the other party may reasonably request in order
to carry out the intent and accomplish the purposes of this Agreement and the
consummation of the transactions contemplated hereby.


 


7.11         No Strict
Construction.  The language used in
this Agreement will be deemed to be the language chosen by the parties to
express their mutual intent, and no rules of strict construction will be
applied against any party.


 


7.12         Legal
Representation.  Digital River
acknowledges that: (a) it has read this Agreement and the exhibits hereto;
(b) it understands that the Company has been represented in the
preparation, negotiation, and execution of this Agreement by Wilson Sonsini
Goodrich & Rosati, Professional Corporation, counsel to the Company;
(c) it has either been represented in the preparation, negotiation, and execution
of this Agreement by legal counsel of its own choice, or has chosen to forego
such representation by legal counsel after being advised to seek such legal
representation; (d) it understands the terms and consequences of this
Agreement and is fully aware of its legal and binding effect.


 


11





















 


IN
WITNESS WHEREOF, the parties hereto have executed this Agreement as of the day
and year first above written.


 


	
   

  	
  INTRAWARE, INC.

  
	
   

  	
   

  	
   

  
	
   

  	
  By:

  	
  /s/ Peter H. Jackson

  
	
   

  	
   

  	
  Name: Peter H. Jackson

  
	
   

  	
   

  	
  Title: Chairman, Chief Executive Officer and

  President

  
	
   

  	
   

  	
   

  
	
   

  	
  DIGITAL RIVER, INC.

  
	
   

  	
   

  	
   

  
	
   

  	
  By

  	
  /s/ Thomas Donnelly

  
	
   

  	
   

  	
  Name: Thomas Donnelly

  
	
   

  	
   

  	
  Title: Chief Financial Officer

  



 


 


[Signature Page to Series B Preferred Stock Purchase
Agreement]