Document:

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                                                                   EXHIBIT 10.1

                                                                  EXECUTION COPY

                         SECURITIES PURCHASE AGREEMENT
                         -----------------------------

     This SECURITIES PURCHASE AGREEMENT ("Agreement")is entered into as of
                                          ---------
August 10, 2000, by and between VOXWARE, INC., a Delaware corporation  (the
"Company"), with principal executive office located at 168 Franklin Corner Road,
 --------
Suite 3, Lawrenceville, New Jersey 08543, and Castle Creek Technology Partners,
LLC, a Delaware limited liability company (the "Purchaser") with principal
                                                ----------
offices located at 77 West Wacker Drive, Suite 4040, Chicago, Illinois 60601.

                                   RECITALS
                                   --------

     A.   The Company and the Purchaser are executing and delivering this
Agreement in reliance upon the exemption from securities registration afforded
by the provisions of Regulation D ("Regulation D"), as promulgated by the United
                                    ------------
States Securities and Exchange Commission (the "SEC") under the Securities Act
                                                ---
of 1933, as amended (the "Securities Act").
                          --------------

     B.   The Purchaser desires to purchase and the Company desires to issue and
sell upon the terms and conditions stated in this Agreement for an aggregate
purchase price of $4,000,000 (i) 4,000 shares (the "Shares of Series A Preferred
                                                    ----------------------------
Stock") of the Company's 7% Series A Convertible Preferred Stock, par value
-----
$0.001 per share and stated value of $1,000 per share (the Series A Preferred
                                                           ------------------
Stock) which shall be governed by the Certificate of Designations in the form
-----
attached hereto as Exhibit A (the "Certificate of Designations") and (ii) a
                   ---------       ----------------------------
warrant in the form attached hereto as Exhibit B (the "Common Stock Warrant") to
                                       ---------       --------------------
purchase a number of shares of the Company's Common Stock, par value $0.001 per
share (the "Common Stock"), equal to 50% of the quotient of (x) the Purchase
            ------------
Price, divided by (y) the Market Price (as defined in the Certificate of
Designations).  The Shares of Series A Preferred Stock and the Common Stock
Warrant are sometimes referred to herein as the "Purchased Securities". The
                                                 --------------------
shares of Common Stock issuable upon the exercise of or otherwise pursuant to
the Common Stock Warrant are referred to as "Warrant Shares".  The shares of
                                             --------------
Common Stock issuable upon the conversion of or otherwise pursuant to the Shares
of Series A Preferred Stock are referred to as "Conversion Shares".  The shares
                                                -----------------
of Series A Preferred Stock, the Common Stock Warrant, the Warrant Shares and
the Conversion Shares are referred to herein as the "Securities".
                                                     ----------

     C.   Contemporaneously with the execution and delivery of this Agreement,
the parties hereto are executing and delivering a Registration Rights Agreement
in the form attached hereto as Exhibit C (the "Registration Rights Agreement"),
                               ---------       -----------------------------
pursuant to which the Company has agreed to provide certain registration rights
under the Securities

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Act, the rules and regulations promulgated thereunder and applicable state
securities laws.

                                  AGREEMENTS
                                  ----------

     NOW, THEREFORE, in consideration of their respective promises contained
herein and other good and valuable consideration, the receipt and sufficiency of
which are hereby acknowledged, the Company and the Purchaser hereby agree as
follows:

                                   ARTICLE I
                   PURCHASE AND SALE OF SECURITIES; SECURITY

     1.1.  Purchase of shares of Series A Preferred Stock and Common Stock
           ---------------------------------------------------------------
Warrant.  The purchase price to be paid by the Purchaser for the shares of
-------
Series A Preferred Stock and the Common Stock Warrant being purchased by the
Purchaser hereunder shall be Four Million Dollars ($4,000,000) (the "Purchase
                                                                     --------
Price").  On the Closing Date (as defined herein), subject to the terms and the
-----
satisfaction (or waiver) of the conditions set forth in Articles VI and VII of
this Agreement,  the Company shall issue and sell to the Purchaser, and the
Purchaser shall purchase from the Company (i) the Shares of Series A Preferred
Stock and (ii) the Common Stock Warrant.

     1.2.  Form of Payment.  At the Closing, the Purchaser shall pay the
           ---------------
Purchase Price for (i) the Shares of Series A Preferred Stock and (ii) the
Common Stock Warrant, by wire transfer of immediately available funds to the
Company, in accordance with the Company's written wiring instructions, and the
Company shall deliver to the Purchaser one or more executed certificates
representing the Shares of Series A Preferred Stock and the Common Stock Warrant
and a duly executed Registration Rights Agreement.

     1.3.  Closing Date.  Subject to the satisfaction (or waiver) of the
           ------------
conditions set forth in Articles VI and VII below, the date and time of the
issuance, sale and purchase of the Purchased Securities pursuant to this
Agreement  (the "Closing") shall be August 14, 2000 (such date being hereinafter
                 -------
referred to as the "Closing Date").  The Closing shall occur on the Closing Date
                    ------------
at 11:00 a.m. New York City time, at the offices of Wolf, Block, Schorr and
Solis Cohen LLP, 250 Park Avenue, New York, New York 10177.

                                  ARTICLE II
                  PURCHASERS' REPRESENTATIONS AND WARRANTIES

     The Purchaser represents and warrants to the Company as follows:

     2.1.  Purchase for Own Account. The Purchaser is purchasing the Purchased
           ------------------------
Securities (and the Conversion Shares and Warrant Shares issuable upon
conversion or exercise of the Purchased Securities, as the case may be) for its
own account and not with a view toward, or in connection with, the public
distribution thereof, and will not resell the Securities except pursuant to
sales that are exempt from the registration requirements of the Securities Act
and/or sales that are registered under the Securities Act.  The

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Purchaser further represents that it does not have any contract, undertaking,
agreement or arrangement with any person to sell, transfer or grant
participation to any third party with respect to any of the Securities. The
Purchaser understands that it must bear the economic risk of this investment
indefinitely, unless any disposition of the Securities is registered pursuant to
the Securities Act and any applicable state securities laws or an exemption from
such registration is available, and that the Company has no present intention of
disposing of any such Securities other than as contemplated by the Registration
Rights Agreement. By making the representations in this Section 2.1, the
Purchaser does not agree to hold any Securities for any minimum or other
specific term and reserves the right to dispose of any or all of the Securities
at any time in accordance with or pursuant to a registration statement or an
exemption from registration under the Securities Act and other applicable state
securities laws.

     2.2.  Accredited Investor Status. The Purchaser is an "accredited investor"
           --------------------------
as that term is defined in SEC Rule 501(a) of Regulation D, as presently in
effect, under the Securities Act.

     2.3.  Reliance on Exemptions. The Purchaser understands that the Purchased
           ----------------------
Securities are being offered and sold to the Purchaser in reliance upon specific
exemptions from the registration requirements of the United States federal and
state securities laws and that the Company is relying upon the truth and
accuracy of the representations and warranties of the Purchaser set forth herein
in order to determine the availability of such exemptions and the eligibility of
the Purchaser to acquire the Securities.

     2.4.  Information. The Purchaser and its counsel have been furnished all
           -----------
materials relating to the business, finances and operations of the Company and
materials relating to the offer and sale of the Purchased Securities which have
been requested by the Purchaser. The Purchaser has been afforded the opportunity
to ask questions of the Company and has received what the Purchaser believes to
be satisfactory answers to any such inquiries. The Purchaser understands and
acknowledges that such discussions, as well as any written information issued by
the Company, (i) were intended to describe the aspects of the Company's business
and prospects which the Company believes to be material, but were not
necessarily an exhaustive description, and (ii) may have contained forward-
looking statements involving known and unknown risks and uncertainties which may
cause the Company's actual results in future periods or plans for future periods
to differ materially from what was anticipated and that, except as specifically
set forth elsewhere herein, no representations or warranties were or are being
made with respect to any such forward-looking statements or the probability of
achieving any of the results projected in any of such forward-looking
statements.  Neither such materials or inquiries nor any other due diligence
investigation conducted by the Purchaser nor any of its representations,
warranties, covenants or agreements shall modify, amend or affect the
Purchaser's right to rely on the Company's representations and warranties
contained in Article III.  The Purchaser understands that the Purchaser's
investment in the Purchased Securities involves a high degree of risk.

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     2.5.  Governmental Review. The Purchaser understands that no United States
           -------------------
federal or state agency or any other government or governmental agency has
passed upon or made any recommendation or endorsement of the Securities or an
investment therein.

     2.6.  Transfer or Resale. The Purchaser understands that (i) except as
           ------------------
provided in the Registration Rights Agreement, the Securities have not been and
are not being registered under the Securities Act or any state securities laws,
and may not be transferred unless subsequently registered thereunder or an
exemption from such registration is available (which exemption the Company
expressly agrees may be established as contemplated in clauses (b) and (c) of
Section 5.1 hereof or as otherwise may be permissible under the Securities Act);
(ii) any sale of such Securities made in reliance on Rule 144 under the
Securities Act (or a successor rule) ("Rule 144") may be made only in accordance
                                       --------
with the terms of said Rule and further, if said Rule is not applicable, any
resale of such Securities without registration under 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 such Securities under the
Securities Act or any state securities laws or to comply with the terms and
conditions of any exemption thereunder (in each case, other than pursuant to
this Agreement or the Registration Rights Agreement).

     2.7.  Legends. The Purchaser understands that, subject to Article V hereof,
           -------
the certificates for the Shares of Series A Preferred Stock and the Common Stock
Warrant and, until such time as the Conversion Shares and Warrant Shares have
been registered under the Securities Act as contemplated by the Registration
Rights Agreement or otherwise, may be sold by the Purchaser pursuant to Rule 144
or otherwise without registration, the certificates for the Conversion Shares
and the Warrant Shares will bear a restrictive legend (the "Legend") in the
                                                            ------
following form:

          THE SECURITIES REPRESENTED BY THIS CERTIFICATE HAVE NOT BEEN
     REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR THE SECURITIES
     LAWS OF ANY STATE OF THE UNITED STATES. THE SECURITIES REPRESENTED HEREBY
     MAY NOT BE OFFERED OR SOLD OR OTHERWISE TRANSFERRED IN THE ABSENCE OF AN
     EFFECTIVE REGISTRATION STATEMENT FOR THE SECURITIES UNDER APPLICABLE
     SECURITIES LAWS OR UNLESS OFFERED, SOLD OR TRANSFERRED PURSUANT TO AN
     AVAILABLE EXEMPTION FROM THE REGISTRATION REQUIREMENTS OF THOSE LAWS.

Except for the Legend in accordance with this Section 2.7 and Section 5.1
hereof, the Securities shall bear no other legend.

     2.8.  Authorization; Enforcement.  This Agreement and the Registration
           --------------------------
Rights Agreement have been duly and validly authorized, executed and delivered
on behalf of

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the Purchaser and are valid and binding agreements of the Purchaser enforceable
against the Purchaser in accordance with their respective terms, except as
enforcement thereof may be limited by (i) laws of general application relating
to bankruptcy, insolvency moratorium, reorganization or other similar laws, both
state and federal, affecting the enforcement of creditors' rights in general,
and (ii) rules of law governing specific performance, injunctive relief and
other equitable remedies.

                                  ARTICLE III
                 REPRESENTATIONS AND WARRANTIES OF THE COMPANY

     The Company represents and warrants to the Purchaser that:

     3.1.  Organization and Qualification.  The Company and each of its
           ------------------------------
subsidiaries is a corporation duly organized, validity existing and in good
standing under the laws of the jurisdiction in which it is incorporated, and has
the requisite corporate power and authority to own its properties and to carry
on its business as now being conducted.  The Company and each of its
subsidiaries is duly qualified as a foreign corporation to do business and is in
good standing in every jurisdiction where the failure to so qualify would have a
Material Adverse Effect.

     For the purpose of this agreement "Material Adverse Effect" means any
                                        -----------------------
material adverse effect on (a) the business, operations, properties, financial
condition or operating results of the Company and its subsidiaries, taken as a
whole on a consolidated basis or (b) the ability of the Company to perform its
obligations under this Agreement, the Series A Preferred Stock, the Common Stock
Warrant and the Registration Rights Agreement (collectively, the "Investment
                                                                  ----------
Agreements").
----------

     3.2.  Authorization; Enforcement.  (a) The Company has the requisite
           --------------------------
corporate power and authority to (i) enter into, and perform its obligations
under each of the Investment Agreements, (ii) issue, sell and perform its
obligations with respect to the Purchased Securities in accordance with the
terms hereof and thereof, (iii) issue the Conversion Shares in accordance with
the terms and conditions of the Certificate of Designations and (iv) issue
Warrant Shares in accordance with the terms and conditions of the Common Stock
Warrant; (b) the execution, delivery and performance of this Agreement and the
other Investment Agreements and the execution and delivery of the by the Company
and the consummation by the Company of each of the transactions contemplated
hereby and thereby (including without limitation the issuance of the Purchased
Securities and the reservation for issuance and issuance of the number of
Conversion Shares and the Warrant Shares initially issuable pursuant to the
conversion of the Series A Preferred Stock and the exercise of the Common Stock
Warrant) have  been duly authorized by all necessary corporate action and no
further consent or authorization of the Company, its board of directors or
stockholders or any other person, body or agency is required with respect to any
of the transactions contemplated hereby or thereby (other than actions of the
SEC and the Company's Board of Directors in connection with the registration of
Conversion Shares and Warrant Shares in accordance with the Registration Rights
Agreement); (c) the Investment Agreements have been duly executed

                                       5
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and delivered by the Company; (d) the Certificate of Designations has been filed
with the Secretary of Delaware; and (e) each of the Investment Agreements
constitutes a legal, valid and binding obligation of the Company enforceable
against the Company in accordance with its terms, except as enforcement thereof
may be limited by (i) laws of general application relating to bankruptcy,
insolvency moratorium, reorganization or other similar laws, both state and
federal, affecting the enforcement of creditors' rights in general, and (ii)
rules of law governing specific performance, injunctive relief and other
equitable remedies.

     3.3.  Capitalization.  The capitalization of the Company as of the date of
           --------------
this Agreement, including the authorized capital stock, the number of shares
issued and outstanding, the number of shares reserved for issuance pursuant to
the Company's stock option plans, the number of shares reserved for issuance
pursuant to securities (other than the Securities), directly or indirectly,
exercisable for, or convertible into or exchangeable for any shares of Common
Stock, the number of shares of Common stock to be initially reserved for
issuance upon conversion of the Shares of Series A Preferred Stock and the
exercise of the Common Stock Warrant is set forth on Schedule 3.3. All
                                                     ------------
outstanding shares of the Company's capital stock have been validly issued,
fully paid and non-assessable.  Except as disclosed in Schedule 3.3, (i) no
                                                       -------------
shares of capital stock of the Company (including the Purchased Securities, the
Warrant Shares and the Conversion Shares) are subject to preemptive rights or
any other similar rights of the stockholders of the Company or any liens or
encumbrances granted or created by the Company preemptive or similar, and (ii)
there are no outstanding debt securities issued by the Company; (iii) there are
no outstanding options, warrants, scrip, rights to subscribe to, calls or
commitments of any character whatsoever relating to, or securities or rights
convertible into, any shares of capital stock of the Company or any of its
subsidiaries, or contracts, commitments, understandings or arrangements by which
the Company or any of its subsidiaries is or may become bound to issue
additional shares of capital stock of the Company or any of its subsidiaries or
options, warrants, scrip, rights to subscribe to, calls or commitments of any
character whatsoever relating to, or securities or rights convertible into, any
shares of capital stock of the Company or any of its subsidiaries; (iv) there
are no agreements or arrangements under which the Company or any of its
subsidiaries is obligated to register the sale of any of their securities under
the Securities Act (except the Registration Rights Agreement)1; (v) there are no
outstanding securities or instruments of the Company or any of its subsidiaries
which contain any redemption or similar provisions, and there are no contracts,
commitments, understandings or arrangements by which the Company or any of its
subsidiaries is or may become bound to redeem a security of the Company or any
of its subsidiaries; and (vi) the Company does not have any stock appreciation
rights or "phantom stock" plans or agreements or any similar plan or agreement.
The Company has furnished or made available to the Purchaser true and correct
copies of the its Certificate of Incorporation as currently in effect

("Certificate of Incorporation"), and its By-laws as currently in effect (the
------------------------------
"By-laws").  The Company has set forth on Schedule 3.3 all instruments and
--------                                  ------------
agreements (other than the Certificate of Incorporation and By-laws) governing
securities convertible

__________________
1 Schedule 3.3 should include the Common Stock Warrant, Shares of Series A
Preferred Stock, the Inroad Warrant, Stratos Warrant and Inroad Registration
Rights Agreement.

                                       6
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into or exercisable or exchangeable for Common Stock or the Company's preferred
stock, par value $0.001 per share ("Preferred Stock") and the Company shall
                                    ---------------
provide to the Purchaser copies thereof upon the request of the Purchaser.
Except as set forth on Schedule 3.3, the Company has no indebtedness for
                       ------------
borrowed money and no agreement providing for indebtedness for borrowed money.
The Company has no subsidiaries, except as provided on Schedule 3.3. All such
                                                       ------------
subsidiaries included on Schedule 3.3. are one hundred percent (100%) owned by
                         ------------
the Company. Except as provided on Schedule 3.3, the Company has no investments,
                                   ------------
either debt or equity, in any other entity.

     3.4.  Issuance of Shares.  The Shares of Series A Preferred Stock are duly
           ------------------
authorized and reserved for issuance, and when issued and delivered in
accordance with the terms hereof will be validly issued, fully paid and non-
assessable, free from all taxes, liens claims and encumbrances and entitled to
the rights and preferences set forth in the Certificate of Designations and are
not and will not be subject to preemptive rights or other similar rights and
will not trigger any anti-dilution or similar provisions in any securities of
the Company or any other agreements to which the Company is party which rights
or provisions have not been waived.  The number of Conversion Shares and the
Warrant Shares initially issuable pursuant to the conversion of the Series A
Preferred Stock and the exercise of the Common Stock Warrant are duly authorized
and reserved for issuance, and, upon conversion of the Series A Preferred Stock
and the exercise of the Common Stock Warrant, each in accordance with its
respective terms, the Conversion Shares and the Warrant Shares will be validly
issued, fully paid and non-assessable, and free from all taxes, liens, claims
and encumbrances and will not be subject to preemptive rights or other similar
rights will not trigger any anti-dilution provisions in any securities of the
Company or any other agreements to which the Company is a party which rights or
provisions have not been waived.

     3.5.  Listing.  The Company's Common Stock is approved for listing and
           -------
quotation on the Nasdaq National Market System and is traded on the Nasdaq
National Market System.  The Company is not aware of any threat to delist or
suspend such quotation, listing and/or trading, including a threat that may be
occasioned by falling below the minimum listing maintenance requirements of the
Nasdaq National Market System.  The Conversion Shares and the Warrant Shares
have been approved for listing, subject to official notice of issuance, on the
Nasdaq National Market System and no further corporate authorization or approval
is required under the rules of the National Association of Securities Dealers
(the "NASD") applicable to the listing (or continued listing) requirements for
      ----
securities on the Nasdaq National Market System, for the issuance of the
Conversion Shares and the Warrant Shares of the Certificate of Designations and
the Common Stock Warrant, as the case may be.  No further authorization or
approval is required for the continued listing of the Common Stock on the Nasdaq
National Market or for the issuance of an aggregate number of Conversion Shares
and Warrant Shares in excess of the Exchange Cap (as defined in the Certificate
of Designations), other than the approval by the stockholders of the Company
pursuant to NASD Rule 4460(I), relating to Nasdaq National Market issuers.

                                       7
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     3.6.  No Conflicts.  The execution, delivery and performance of each of the
           ------------
Investment Agreement, by the Company and the consummation by the Company of the
transactions contemplated hereby and thereby (including the issuance of the
Purchased Securities and the reservation for issuance, as applicable, of the
Warrant Shares and the Conversion Shares do not and will not (a) result in a
violation of the Certificate of Incorporation or By-laws of the Company or any
of its subsidiaries, (b) 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 agreement, indenture or instrument to which the Company or
any of its subsidiaries is a party (except for such conflicts, defaults,
terminations, amendments, accelerations, and cancellations as would not,
individually or in the aggregate, have a Material Adverse Effect), or (c)
assuming the accuracy of the Purchaser's representations and warranties set
forth in Article II hereof, result in a violation of any law, rule, regulation,
order, judgment or decree (including, without limitation, U.S. federal and state
securities laws and regulations) 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.  Neither the Company nor any of its
subsidiaries is in violation of its certificate of incorporation, by-laws or
other organizational documents, and neither the Company nor any of its
subsidiaries is in default (and no event has occurred which, with notice or
lapse of time or both, would put the Company or any of its subsidiaries in
default) under, nor to the Company's knowledge, has there occurred any event
giving others (with notice or lapse of time or both) any rights of termination,
amendment, acceleration or cancellation of, any agreement, indenture or
instrument to which the Company or any of its subsidiaries is a party. The
business of the Company and its subsidiaries is not being conducted in violation
of any law, ordinance, rule,  regulation, order, judgment or decree of any
governmental entity, court or arbitration tribunal in any material respect.  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 or entity or authority in order for it to
execute, deliver or perform any of its obligations under any of the Investment
Agreements or to perform its obligations in accordance with the terms hereof or
thereof.

     3.7.  SEC Documents; Financial Statements.  The Common Stock is registered
           -----------------------------------
under Section 12 of the Securities Exchange Act of 1934, as amended (the

"Exchange Act") and has been so registered since October 30, 1996.  The Company
-------------
has timely 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 Exchange Act or pursuant to the registration and reporting requirements
of the Securities Act (all of the foregoing filed after June 30, 1998, and all
exhibits included therein and financial statements and schedules thereto and
documents incorporated by reference therein, and all correspondence to and from
the SEC related thereto, being referred to herein as the "SEC Documents").
                                                          -------------
Schedule 3.7 sets forth a complete list of the SEC Documents.  The Company has
------------
delivered or made available to the Purchaser true and complete 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

                                       8
<PAGE>

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. None of the
statements made in any such SEC Document is, or has been, required to be updated
or amended under applicable law, except as listed on Schedule 3.7. The financial
                                                     ------------
statements of the Company included in the SEC Documents were prepared in
accordance with U.S. generally accepted accounting principles, consistently
applied, and the rules and regulations of the SEC during the periods involved
and present accurately and completely the consolidated financial position of the
Company and its consolidated subsidiaries as of the dates thereof and the
                                                -----------------
consolidated results of their operations and cash flows for the periods then
ended (subject, in the case of unaudited statements, to normal, immaterial year-
end audit adjustments). Except as set forth in the financial statements of the
Company included in the SEC Documents, the Company has no liabilities,
contingent or otherwise, other than (i) liabilities incurred subsequent to the
date of such financial statements in the ordinary course of business consistent
with past practice and (ii) obligations under contracts and commitments incurred
in the ordinary course of business and not required under generally accepted
accounting principles to be reflected in such financial statements, in each case
of clause (i) and (ii) next above which, individually and in the aggregate, are
not material to the financial condition, business, operations, properties or
operating results of the Company and its subsidiaries taken on a whole. The
Company meets the requirements for use of Form S-3 for registration of the
resale of Registrable Securities, as defined in the Registration Statement.

     3.8.  Absence of Certain Changes.  Except as set forth in Schedule 3.8,
           --------------------------                          ------------
since March 31, 2000, there has been no change and no development in the
business, properties, operations, financial condition or results of operations
of the Company which individually or in the aggregate could reasonably be
expected to have a Material Adverse Effect.
                   -----------------------

     3.9.  Absence of Litigation.  Except as disclosed in Schedule 3.9 or the
           ---------------------                          ------------
SEC Documents, there is no action, suit, proceeding, inquiry or investigation
before or by any court, public board, governmental agency or authority, or self-
regulatory organization or body pending or, to the knowledge of the Company or
any of its subsidiaries, threatened against or affecting the Company, any of its
subsidiaries, or any of their respective directors or officers in their
capacities as such, wherein an unfavorable decision, ruling or finding could
have a Material Adverse Effect or would adversely affect the transactions
contemplated by this Agreement or any of the documents contemplated hereby or
which would adversely affect the validity or enforceability of, or the authority
or ability of the Company to perform its obligations under, this Agreement or
any of such other documents.  To the Company's knowledge, there are no facts
which, if known by a potential claimant or governmental agency or authority,
could give rise to a claim or proceeding against the Company or any of its
subsidiaries which, if asserted or conducted with results unfavorable to the
Company or any of its subsidiaries, could have a Material Adverse Effect.

                                       9
<PAGE>

     3.10.  Disclosure.  No information relating to or concerning the Company
            ----------
set forth in this Agreement or provided to the Purchaser in connection with the
transactions contemplated hereby contains an untrue statement of a material fact
or omits to state a material fact necessary in order to make the statements made
herein or therein, in light of the circumstances under which they were made, not
misleading.  No event or circumstance has occurred or exists with respect to the
Company or its subsidiaries or their respective businesses, properties,
prospects, operations or financial conditions, which has not been publicly
disclosed other than the transactions contemplated hereby.  There is no fact
(other than matters of a general economic or political nature which do not
uniquely affect the business, properties, operations or financial condition of
the company) known to the Company that has not been disclosed by the Company to
the Purchaser and to the public that might reasonably be expected to have or
result in a material effect on the business, properties, operations or financial
condition of the Company and its subsidiaries taken as a whole or have a
material effect on the ability of the Company to conduct its business after the
Closing in all material respects as currently conducted.

     3.11.  Acknowledgment Regarding Purchaser's Purchase of the Securities.
            ---------------------------------------------------------------
The Company acknowledges and agrees that the Purchaser is acting independently
and is not acting as a financial advisor or fiduciary of the Company (or in any
similar capacity) with respect to this Agreement or the transactions
contemplated hereby, that this Agreement and the transactions contemplated
hereby, and the relationship between the Purchaser and the Company is "arms-
length", and that any statement made by the Purchaser, or any of its
representatives or agents, in connection with this Agreement or the transactions
contemplated hereby, other than the representations and warranties of the
Purchaser contained herein, is not advice or a recommendation, is merely
incidental to the Purchaser's purchase of the Securities and has not been relied
upon in any way by the Company, its officers, directors or other
representatives.  The Company further represents to the Purchaser that the
Company's decision to enter into this Agreement and the transactions
contemplated hereby has been based solely on an independent evaluation by the
Company and its representatives.

     3.12.  No General Solicitation. Neither the Company nor any person acting
            -----------------------
on behalf of the Company has conducted any "general solicitation," as described
in Rule 502(c) under Regulation D, with respect to any of the Securities being
offered hereby.

     3.13.  No Integrated Offering.  Neither the Company, nor any of its
            ----------------------
affiliates, nor any person acting on its or 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 prevent the parties hereto from
consummating the transactions contemplated hereby pursuant to an exemption from
registration under the Securities Act pursuant to the provisions of Regulation
D.  The transactions contemplated hereby are exempt from the registration
requirements of the Securities Act, assuming the accuracy of the representations
and warranties herein contained of the Purchaser to the extent relevant for such
determination.

                                       10
<PAGE>

     3.14.  No Brokers.  The Company has taken no action which would give rise
            ----------
to any claim by any person for brokerage commissions, finder's fees or similar
payments by the Purchaser relating to this Agreement or the transactions
contemplated hereby, except for dealings with Institutional Finance Group, Inc.,
the fees and expenses of which shall be paid in full by the Company.

     3.15.  Acknowledgment of Dilution.  The potential number of Conversion
            --------------------------
Shares and Warrant Shares issuable to the Purchaser may increase substantially
in certain circumstances, including the circumstance wherein the trading price
of the Common Stock declines.  The Company's executive officers and directors
have studied and fully understand the terms of this Agreement and the
transactions contemplated hereby and the nature of the securities being sold
hereunder and recognize that they have a potential dilutive effect.  The board
of directors of the Company has concluded in its good faith business judgment
that the issuance of the Securities as contemplated hereby is in the best
interests of the Company. The Company acknowledges that its obligation to issue
Conversion Shares and Warrant Shares in accordance with the terms of the
Certificate of Designations and the Common Stock Warrant, respectively, and such
obligation is binding upon it and enforceable regardless of the dilution that
such issuance may have on the ownership interests of other stockholders.

     3.16.  Intellectual Property.  Except as set forth in the SEC Documents, to
            ---------------------
the Company's knowledge each of the Company and its subsidiaries, owns or
possesses adequate and enforceable rights to use all patents, patent
applications, trademarks, trademark applications, trade names, service marks,
copyrights, copyright applications, licenses, know-how (including trade secrets
and other unpatented and/or unpatentable proprietary or confidential
information, systems or procedures) and other similar rights and proprietary
knowledge (collectively, "Intangibles") used or necessary for the conduct of its
                          -----------
business as now being conducted and as described in the Company's SEC Documents.
Except as set forth in the SEC Documents, neither the Company nor any subsidiary
of the Company infringes on or is in conflict with any right of any other person
with respect to any Intangibles nor is there any claim of infringement made by a
third party against or involving the Company or any of its subsidiaries, which
infringement, conflict or claim, individually or in the aggregate, if the
subject of an unfavorable decision, ruling or finding, would have a Material
Adverse Effect.  Except as set forth in the SEC Documents, none of the
Intangibles used in the Company's business is expected to expire or terminate
within two years from the date of this Agreement, except where such expiration
or termination would not result, either individually or in the aggregate, in a
Material Adverse Effect.  The Company and its subsidiaries have taken reasonable
security measures to protect the secrecy, confidentiality and value of all of
their Intangibles.

     3.17.  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 subsidiary has, in the course of his 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

                                       11
<PAGE>

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 bribe, rebate,
payoff, influence payment, kickback or other unlawful payment to any foreign or
domestic government official or employee. Without limiting the generality of the
foregoing, the Company and its subsidiaries have not directly or indirectly made
or agreed to make (whether or not said payment is lawful) any payment to obtain,
or with respect to, sales other than usual and regular compensation to its or
their employees and sales representatives with respect to such sales.

     3.18.  Officers and Directors.  No executive officer (as defined in Rule
            ----------------------
501(f) promulgated under the Securities Act) or director of the Company or any
of its subsidiaries, is, or is now expected to be, in violation of any material
term of any employment contract, confidentiality, disclosure or proprietary
information agreement, non-competition agreement, or any other contract or
agreement or any restrictive covenant between such officer or director and the
Company and its subsidiaries or between the such officer or director and any
other third party.  No officer or director has, to the knowledge of the Company
and its subsidiaries, any intention to terminate or limit his or her employment
with, or services to, the Company or any of its subsidiaries, nor is any such
officer subject to any constraints which would cause such person to be unable to
devote his full time and attention to such employment or services.

     3.19.  Solvency.  As of the Closing, the Company (i) has not incurred and
            --------
does not intend to incur, or believe that it will incur, debts beyond its
ability to pay such debts as they become due, (ii) owns assets, the fair
saleable value of which is  greater than the total amount of its liabilities
(including contingent liabilities), and (iii) has and will have capital that is
not unreasonably small in relation to its business as presently conducted and as
proposed to be conducted.

     3.20.  Title to Properties; Liens and Encumbrances.  The Company has good
            -------------------------------------------
and marketable title to all of its material properties and assets, both real and
personal, and has good title to all its leasehold interests, in each case
subject only to mortgages, pledges, liens, security interests, conditional sale
agreements, encumbrances or charges created in the ordinary course of business.

     3.21.  Employment Matters.  The Company is in compliance in all material
            ------------------
respects with all presently applicable provisions of the Employee Retirement
Income Security Act of 1974, as amended, including the regulations and published
interpretations thereunder ("ERISA"); no "reportable event" (as defined in
                             -----
ERISA) has occurred with respect to any "pension plan" (as defined in ERISA) for
which the Company would have any liability; the Company has not incurred and
does not expect to incur liability under (i) Title IV of ERISA with respect to
termination of, or withdrawal from, any "pension plan" or (ii) Sections 412 or
4971 of the Internal Revenue Code of 1986, as amended, including the regulations
and published interpretations thereunder (the "Code"); and each "pension plan"
                                               ----
for which the Company would have any liability that is intended to be qualified
under Section 401(a) of the Code is so qualified in all material respects and
nothing has

                                       12
<PAGE>

occurred, whether by action or by failure to act, which would cause the loss of
such qualification. Neither the Company nor any of its subsidiaries is involved
in any union labor dispute nor, to the knowledge of the Company or any of its
subsidiaries, is any such dispute threatened. To the knowledge of the Company,
none of the Company's or its subsidiaries' employees is a member of a union
which relates to such employee's relationship with the Company. Neither the
Company nor any of its subsidiaries is a party to a collective bargaining
agreement, and the Company and its subsidiaries believe that their relations
with their employees are good.

     3.22.  Insurance.  The Company maintains property and casualty, general
            ---------
liability, personal injury, director and officer liability and other similar
types of insurance with financially sound and reputable insurers that is
adequate, consistent with industry standards and the historical claims
experience of the Company and its subsidiaries.  The Company has not received
notice from, and has no knowledge of any threat by, any insurer (that has issued
any insurance policy to the Company or any of its subsidiaries) that such
insurer intends to deny coverage under or cancel, discontinue or not renew any
insurance policy covering the Company or any of its subsidiaries presently in
force.

     3.23.  Taxes. All applicable tax returns required to be filed by the
            -----
Company and each of its subsidiaries have been prepared and filed in compliance
with all applicable laws, or if not yet filed have been granted extensions of
the filing dates which extensions have not expired, and all taxes, assessments,
fees and other governmental charges upon the Company, its subsidiaries, or upon
any of their respective properties, income or franchises, shown in such returns
and on assessments received by the Company or its subsidiaries to be due and
payable have been paid, or adequate reserves therefor have been set up if any of
such taxes are being contested in good faith; or if any of such tax returns have
not been filed or if any such taxes have not been paid or so reserved for, the
failure to so file or to pay would not in the aggregate have a Material Adverse
Effect.

     3.24.  Internal Controls.  The Company maintains a system of internal
            -----------------
accounting controls sufficient to provide reasonable assurances that (i)
transactions are executed in accordance with management's general or specific
authorization; (ii) transactions are recorded as necessary to permit preparation
of financial statements in conformity with generally accepted accounting
principles and to maintain accountability for assets; (iii) access to assets is
permitted only in accordance with management's general or specific
authorization; and (iv) the recorded accountability for assets is compared with
existing assets at reasonable intervals and appropriate action is taken with
respect to any differences.

     3.25.  Contracts. The SEC Documents, as supplemented by  Schedule 3.25
            ---------                                        --------------
hereto, contain a complete and accurate list of all material undischarged
written or oral contracts, agreements, leases or other instruments to which the
Company or any subsidiary is a party or by which the Company or any subsidiary
is bound or to which any of the properties or assets of the Company or any
subsidiary is subject (each a "Contract").  None of the Company, its
                               --------
subsidiaries or, to the knowledge of the Company, any of the other parties
thereto, is in breach or violation of any Contract, which breach or

                                       13
<PAGE>

violation relates to indebtedness for borrowed money, is with respect to an
obligation in excess of Seventy-Five Thousand Dollars ($75,000) or would have a
Material Adverse Effect. No event, occurrence or condition exists which, with
the lapse of time, the giving of notice, or both, or the happening of any
further event or condition, would become a breach or default by the Company or
its subsidiaries under any Contract which breach or default would have a
Material Adverse Effect.

     3.26.  Year 2000 Processing.  The computer systems used by the Company and
            --------------------
its subsidiaries (the "Systems"), both hardware and software, are in good
                       -------
working order.  The occurrence of the year 2000 has not materially and adversely
affected the Systems of the Company, its subsidiaries, or their business, and no
material expenditures in excess of currently budgeted items are or will be
required in order to cause such Systems to operate properly as a result of the
change of the year 1999 to 2000.  The Company and its subsidiaries have resolved
any issues discovered as a result of year 2000 inquires and compliance testing
or otherwise known to the Company.

     3.27.  Environmental Matters.  Neither the Company and its subsidiaries,
            ---------------------
nor to the Company's knowledge, any predecessor in interest, has ever caused or
permitted any Hazardous Material (as defined below) to be released, treated or
disposed of on, at, under or within any real property owned, leased or operated
by the Company and its subsidiaries or any predecessor in interest, and no such
real property has ever been used (either by the Company and its subsidiaries or
any predecessor in interest ) as a treatment, storage or disposal site for any
Hazardous Material.  The Company has no liabilities with respect to Hazardous
Materials, and to the Company's knowledge, no facts or circumstances exist which
could give rise to liabilities with respect to Hazardous Materials, which could
have any reasonable likelihood of having a Material Adverse Effect on the
Company.  For purposes of this Agreement "Hazardous Materials" shall mean (a)
                                          -------------------
any pollutants or contaminations, (b) any asbestos or insulation or other
material composed of or containing asbestos and (c) any petroleum product and
any hazardous, toxic or dangerous waste, substance or material defined as such
in, or for purposes of, the Comprehensive Environmental Response, Compensation
and Liability Act, any so-called "Superfund" or "Superlien" law, or (d) any
other applicable federal, state, local or other statute, law, ordinance, code,
rule, regulation, order or decree concerning the protection of human health or
the environment or otherwise regulating, relating to, or imposing liability or
standards of conduct concerning, any hazardous, toxic or dangerous waste,
substance or material, as now or at any time hereafter in effect.

     3.28.  Regulatory Permits.  Except for Permits (as defined below) the
            ------------------
absence of which would not result, either individually or in the aggregate, in 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 (the "Permits"), and neither the Company nor any such Subsidiary has
                 -------
received any notice of proceedings relating to the revocation or modification of
any such Permit.

                                       14
<PAGE>

     3.29.  Transactions With Affiliates.  Except as set forth in the SEC
            ----------------------------
Documents and other than the grant of stock options disclosed on Schedule 3.29,
                                                                 -------------
none of the officers, directors or employees of the Company is presently a party
to any transaction with the Company or any of its subsidiaries (other than for
services as employees, officers and directors), including any contract,
agreement or other arrangement providing for the furnishing of services to or
by, providing for rental of real or personal property to or from, or otherwise
requiring payments to or from any such officer, director or employee or, to the
knowledge of the Company, any corporation, partnership, trust or other entity in
which any such officer, director, or employee has a substantial interest or is
an officer, director, trustee or partner.

     3.30.  Application of Takeover Protections.  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 Certificate of Incorporation or the laws of the
state of its incorporation which is or could become applicable to the Purchaser
as a result of the transactions contemplated by the Investment Agreements,
including, without limitation, the Company's issuance of the Securities and the
Purchaser's ownership of the Securities.

                                  ARTICLE IV
                                   COVENANTS

     4.1.  Efforts.  The Company and the Purchaser shall use commercially
           -------
reasonable efforts timely to satisfy each of the conditions described in Article
VI and VII of this Agreement.

     4.2.  Securities Laws.  The Company agrees to file a Form D with respect to
           ---------------
the Securities with the SEC as required under Regulation D and to provide a copy
thereof to the Purchaser within fifteen (15) days of the Closing.  The Company
agrees to file a Current Report on Form 8-K disclosing this Agreement and the
transactions contemplated hereby with the SEC within one (1) business day
following the Closing Date.  Such Form 8-K shall contain as exhibits this
Agreement, the form of Certificate of Designations, the form of Common Stock
Warrant and the form of Registration Rights Agreement.  The Company shall, on or
prior to the Closing, take such action as is necessary to sell the Shares of
Series A Preferred Stock and Common Stock Warrant to the Purchaser in accordance
with applicable securities laws of the states of the United States, and shall
provide evidence of any such action so taken to the Purchaser on or prior to the
date of the applicable Closing.  Without limiting any of the Company's
obligations under any Investment Agreement from and after the Closing Date,
neither the Company nor any person acting on its behalf shall take any action
which would adversely affect any exemptions from registration under the
Securities Act with respect to the transactions contemplated hereby.

     4.3.  Reporting Status.  So long as the Purchaser beneficially owns any
           ----------------
Securities, the Company shall timely file all reports required to be filed with
the SEC

                                       15
<PAGE>

pursuant to the Exchange Act, and the Company shall not terminate its status as
an issuer required to file reports under the Exchange Act even if the Exchange
Act or the rules and regulations thereunder would permit such termination.

     4.4.  Use of Proceeds. The Company shall use the proceeds from the sale of
           ---------------
the Securities for general corporate purposes only, in the ordinary course of
its business and consistent with past practice and, without limiting the
generality of the foregoing, shall not use such proceeds to make a loan to any
employee, officer, director or stockholder of the Company, to repay any loan or
other obligation of the Company to any such person or to repurchase or pay a
dividend on shares of Common Stock or other securities of the Company, other
than any such payment explicitly required or permitted by the terms of this
Agreement, the Certificate of Designations or the other Investment Agreements.

     4.5.  Financing Restrictions.  During the period beginning on the Closing
           ----------------------
Date and ending on the date which is three (3) months following the effective
date of the registration statement contemplated by Section 2.1 of the
Registration Rights Agreement (the "Effective Date") (provided, however, that
                                    --------------
such period shall be extended by the number of days equal to the number of days
during which there is a Registration Suspension (as defined in the Registration
Rights Agreement) during such period) (the "Financing Restriction Period", the
                                            ----------------------------
Company shall not, and shall cause its direct and indirect subsidiaries not to,
issue or agree to issue any equity, equity-like or equity-linked securities of
the Company or any security convertible into or exercisable or exchangeable,
directly or indirectly, for equity, equity-like or equity-linked securities of
the Company, other than Excluded Securities (any such securities, "Restricted
                                                                   ----------
Securities").  The term "Excluded Securities" means capital stock issued and
-----------              -------------------
sold by the Company:  (i) to the Purchaser pursuant to this Agreement and the
Common Stock Warrant, including the Warrant Shares and the Conversion Shares,
(ii) pursuant to any employee stock option, stock purchase or restricted stock
plan of the Company, so long as the issuance of such stock or option is approved
by a committee of independent directors of the Company, (iii) pursuant to
strategic investments, the primary purpose of each of which is not to raise
equity capital and provided that such strategic investors shall be prohibited
from reselling their shares of the Company's capital stock during such Financing
Restriction Period and further provided that if the Company requests a waiver of
the reselling prohibition set forth in this subclause (iii) and demonstrates to
the Purchaser that a potential strategic investor is unable to make a strategic
investment in the Company as a consequence of such reselling prohibition,
Purchaser will not unreasonably withhold its consent to the waiver of the
reselling prohibition set forth in this subclause (iii) with respect to such
strategic investment, (iv) in a firm commitment underwritten public offering,
where the net proceeds to the Company exceed $15 million, (v) pursuant to
warrants dated as of April 4, 2000 (the "Inroad Warrants") to purchase an
                                         ---------------
aggregate of 325,000 shares of Common Stock issued in connection with the
Company's acquisition of Inroad, Inc. in April 2000 (the "Inroad Acquisition"),
                                                          ------------------
(vi) 650,000 shares of Common Stock issued to Inroad, Inc. in connection with
the Inroad Acquisition, (vii) warrants dated as of April 4, 2000 (the "Stratos
                                                                       -------
Warrants") to purchase an aggregate of 50,000 shares of Common Stock issued to
--------
Stratos Product Development LLC ("Stratos") in connection with the Inroad
                                  -------
Acquisition and (viii) warrants to purchase an aggregate of

                                       16
<PAGE>

50,000 shares of Common Stock to be issued to Institutional Finance Group, Inc.
in connection with the transactions contemplated hereby.

     4.6.  Additional Registrations.  Except for the Excluded Securities
           ------------------------
described in subclauses (i), (ii), (iv), (v), (vi) or (vii) of the definition of
Excluded Securities, the Company will not cause any Restricted Securities or any
Excluded Securities to be covered by a registration statement that is to be
filed or declared effective by the Commission until the earlier to occur of (A)
the expiration of the Financing Restriction Period or (B) the date that the
registration statement filed by the Company pursuant to its obligations under
the Registration Rights Agreement has been effective under the Securities Act
for a period of at least one-hundred and eighty (180) days, during which one
hundred eighty (180) day period the Company shall not have notified the
Purchaser that such registration statement or the prospectus included in such
registration statement includes an untrue statement of a material fact or omits
to state a material fact required to be stated therein in order to make the
statements therein, in light of the circumstances under which they were made,
not misleading.

     4.7.  Right of First Refusal.  During the nine (9) months period beginning
           ----------------------
on the date immediately following the final day of the Financing Restriction
Period, the Company shall not, and shall cause each of its direct and indirect
subsidiaries not to, issue or agree to issue or offer to issue or solicit any
offer or inquiry with regard to any Restricted Securities unless the Company has
satisfied or has caused its subsidiary to satisfy all of the following
requirements with respect to such issuance:

          (a) The Company or the subsidiary shall have delivered a notice to the
Purchaser (the "Transfer Notice"), which notice shall include (A) the terms and
                ---------------
conditions of the securities and the consideration per unit which the Company or
the subsidiary desires to receive for the securities (which, in the case where
the Company or the subsidiary shall have received an offer to purchase such
securities other than from the Purchaser (a "Third Party Offer") shall be the
                                             -----------------
consideration set forth in such offer) and (B) all of the material terms and
conditions, including the terms and conditions of payment, upon which the
Company, or the subsidiary proposes to transfer said securities (which, in the
case of a Third Party Offer, shall be the terms and conditions set forth in the
Third Party Offer).

          (b) Upon the delivery of the Transfer Notice, the Purchaser shall have
an option to purchase (i) up to one-third of the aggregate number of the
securities described therein or (ii) all, but not greater than one-third and
less than all, of the securities described therein.  Such option shall be
exercisable by the Purchaser by service of written notice upon the Company or
the subsidiary within ten (10) business days of receipt of the Transfer Notice.

          (c) If the option created in clause (b) hereof is not exercised by
Purchaser within ten (10) business days of service of the Transfer Notice, or if
such option is exercised only in part, (to the extent permitted by clause (b)
hereof), then, within a period of thirty (30) days beginning on the day
following the date of expiration

                                       17
<PAGE>

of the option period, the Company or the subsidiary may issue some or all of the
securities sought to be issued as to which such option was not exercised, at a
price which is not less than one hundred percent (100%) of the price specified
in the Transfer Notice and on terms and conditions not less favorable to the
Company or the subsidiary than those specified in the Transfer Notice.

     4.8.  Expenses.  The Company shall pay to Castle Creek Technology Partners
           --------
LLC  ("CC") or its designee, up to Thirty Thousand ($30,000.00) Dollars, as
reimbursement for the expenses incurred by CC and its affiliates and advisors in
connection with the negotiation, preparation, execution, and delivery of this
Agreement and the other agreements and documents to be executed in connection
herewith, including, without limitation, CC's and its affiliates' and advisors'
due diligence and  reasonable attorneys' fees and expenses (the "Expenses") upon
                                                                 --------
presentation of documentary evidence of such Expenses.  The Company shall
reimburse CC at the Closing for such Expenses, and thereafter upon CC's written
request therefor, subject to such $30,000.00 limit.

     4.9.  Listing Requirements.  The Company shall continue the trading and
           --------------------
listing of its Common Stock on the Nasdaq National Market or the New York Stock
Exchange and shall include in such listing the Warrant Shares and the Conversion
Shares and shall comply in all respects with the Company's filing and other
obligations under the rules of the NASD or the New York Stock Exchange as
applicable and shall not permit the suspension or termination of any such
trading and listing, and if such trading and listing of Common Stock is
suspended or terminated, the Company will use its reasonable best efforts to
requalify its Common Stock or otherwise cause such trading and listing to
resume.  The Company shall promptly provide to the Purchaser copies of any
notices it receives from the NASD regarding the continued eligibility of the
Common Stock for listing and trading on the Nasdaq National Market.  The Company
shall pay all fees and expenses in connection with satisfying its obligations
under this Section 4.9.

     4.10.  Corporate Existence.  So long as the Purchaser beneficially owns any
            -------------------
Securities, the Company shall maintain its corporate existence, except in the
event of a  Major Transaction (as defined in the Certificate of Designations)
merger, consolidation or sale of all or substantially all of the Company's
assets, as long as the surviving or successor entity in such transaction (i)
assumes the Company's obligations hereunder and under the agreements and
instruments entered into in connection herewith regardless of whether or not the
Company would have had a sufficient number of shares of Common Stock authorized
and available for issuance in order to effect the conversion of all Series A
Preferred Stock outstanding as of the date of such transaction and (ii) is a
publicly traded corporation whose Common Stock is quoted and listed for trading
on the Nasdaq National Market or the New York Stock Exchange.

     4.11.  Reserved Amount; Allocation of Exchange Cap.
            --------------------------------------------

            (a) The Company shall at all times reserve and keep available out of
its authorized but unissued shares of Common Stock a sufficient number of shares
of

                                       18
<PAGE>

Common Stock to provide for the (i) full conversion of all Shares of Series A
Preferred Stock and payment in shares of Common Stock of all accrued and unpaid
dividends on Shares of Series A Preferred Stock and (ii) the exercise, in whole
and not in part, of the Common Stock Warrant and issuance of the Warrant Shares
in connection therewith. In the event that any approvals, including stockholder
approval are required to increase the number of Shares of Common Stock reserved
for issuance as provided in the preceding sentence, the Company shall take all
actions necessary to obtain such approval(s) as soon as possible.

          (b) To the extent that the Exchange Cap (as defined in the Certificate
of Designations) would limit at any time or from time to time the number of
Conversion Shares and/or Warrant Shares then issuable, the number of shares of
Common Stock issuable upon the conversion of Series A Preferred Stock and
exercise of the Common Stock Warrants shall be allocated pro rata to the holders
of the Series A Preferred Stock and holders of Common Stock Warrants in the same
proportion as the aggregate number of Conversion Shares and Warrant Shares
issuable to a holder (without reference to the Exchange Cap) bears to all
Conversion Shares and Warrant Shares issuable to all holders (without reference
to the Exchange Cap).

          (c) The Company shall promptly deliver to each holder of Series A
Preferred Stock and each holder of Common Stock Warrant(s) a written report
notifying the holder of any occurrence which prohibits the Company from issuing
Common Stock upon conversion of the Series A Preferred Stock or exercise of the
Common Stock Warrant(s).  Such  report shall also specify (i) the total number
of shares of Series A Preferred Stock outstanding as of the date of the report
and the total number of Common Stock Warrant(s) outstanding as of the date of
the report, (ii) the total number of shares of Common Stock issued upon all
conversions of Series A Preferred Stock through the date of the report and the
total number of shares of Common Stock issued upon the exercise of Common Stock
Warrant(s) through the date of the report, (iii) the total number of shares of
Common Stock which are reserved for issuance upon conversion of the Series A
Preferred Stock as of the date of the report and the total number of shares of
Common Stock which are reserved for issuance upon the exercise of the Common
Stock Warrant(s) as of the date of the report, (iv) the total number of shares
of Common Stock which may thereafter be issued by the Company upon conversion of
the Series A Preferred Stock and the total number of shares of Common Stock
which may thereafter be used by the Company upon the exercise of the Common
Stock Warrant(s) before the Company would exceed the Exchange Cap and (v) the
amount of the Conversion Price (as defined in the Certificate of Designations)
and Exercise Price (as defined in the Common Stock Warrant) as of the date of
the report.   Upon request of any holder of Series A Preferred Stock or any
holder of Common Stock Warrant, the Company shall promptly confirm for such
holder that sufficient shares of Common Stock are reserved for issuance upon
conversion of such holder's Series A Preferred Stock or such holder's of Common
Stock Warrant, as the case may be, as of the date of the report.

     4.12.  Transactions with Affiliates. The Company and each of its
            ----------------------------
subsidiaries will not enter into any agreement or arrangement, written or oral,
directly or indirectly,

                                       19
<PAGE>

with any officer, director, employee or other person holding in excess of 5% of
the Company's capital stock or any other person controlling, controlled by or
under common control with the Company, or provide services or sell goods to, or
for the benefit of, or pay or otherwise distribute monies, goods or other
valuable consideration to, an affiliate, except upon fair and reasonable terms
no less favorable to the Company and each of its subsidiaries than terms in a
comparable arm's length transaction with an unaffiliated person or entity and
except for existing intercompany debt and upon the approval of the disinterested
members of the Company's Board of Directors, after full disclosure.

     4.13.  Limitation of Agreements.  The Company will not, and will not permit
            ------------------------
any subsidiary to, enter into any contract, or any amendment, modification,
extension or supplement to any existing contract, which contractually prohibits
the Company from performing its obligations under the Series A Preferred Stock
or any of the other Investment Agreements.

     4.14.  Exchange Cap.  If, at any time or from time to time, in the
            -------------
reasonable judgment of the Purchaser (or the holders of a majority of the
Registrable Shares (as defined in the Registration Rights Agreement) issuable
upon conversion of or otherwise pursuant to the Series A Preferred Stock or upon
the exercise in whole and not in part of the Common Stock Warrant(s)) an
ambiguity exists relating to the Exchange Cap, including the applicability of
the Exchange Cap at any time or from time to time to the holders of Series A
Preferred Stock and/or holders of Common Stock Warrant(s), the Company shall use
commercially reasonable efforts to (i) assist the Purchaser or such holders, as
the case may be, in obtaining clarification from the NASD or any other exchange
on which Common Stock is then listed of the rules of or relating to the Exchange
Cap and any other rules and regulations applicable to maintaining the listing
and trading of the Common Stock on the Nasdaq National Market, or any other
exchange on which the Common Stock is then listed, and (ii) to obtain all
approvals required to maintain the listing and trading of the Common Stock on
the Nasdaq National Market, or any other exchange on which the Common Stock is
then listed, including if applicable, the approval of the Company's stockholders
as required by NASD Rule 4460 (with respect to Nasdaq National Market issuers)
or the New York Stock Exchange Rules.

     4.15.  Bankruptcy Waiver.  In the event the Company becomes a debtor under
            -----------------
the Bankruptcy Code, the Company hereby waives to the fullest extent permitted
any rights to relief it may have under 11 U.S.C. 362 in respect of the
conversion of the Shares of Series A Preferred Stock and the exercise of the
Common Stock Warrant.  At the direction of Purchaser, the Company agrees,
without cost or expense to the Purchaser, to take or consent to any and all
action necessary to effectuate relief under 11 U.S.C. 362.

                                   ARTICLE V
                  LEGEND REMOVAL, TRANSFER AND CERTAIN SALES

     5.1.  Removal of Legend.  The Legend shall be removed and the Company shall
           -----------------
issue a certificate without any legend to the holder of any Security upon which
such Legend is stamped, and a certificate for a Security shall be originally
issued without the

                                       20
<PAGE>

Legend if (a) the sale of such Security is registered under the Securities Act,
(b) such holder provides the Company with an opinion of counsel, in form,
substance and scope customary for opinions of counsel in comparable transactions
to the effect that a public sale or transfer of such Security may be made
without registration under the Securities Act or (c) such Security can be sold
pursuant to Rule 144. The Purchaser agrees to sell all Securities, including
those represented by a certificate(s) from which the Legend has been removed, or
which were originally issued without the Legend, pursuant to an effective
registration statement and to deliver a prospectus in connection with such sale
or in compliance with an exemption from the registration requirements of the
Securities Act. In the event the Legend is removed from any Security or any
Security is issued without the Legend and thereafter the effectiveness of a
registration statement covering the resale of such Security is suspended or a
supplement or amendment thereto is required by applicable securities laws, then
upon reasonable advance notice to each Purchaser holding such Security, the
Company may require that the Legend be placed on any such Security that cannot
then be sold pursuant to an effective registration statement or Rule 144 or with
respect to which the opinion referred to in clause (b) next above has not been
rendered, which Legend shall be removed when such Security may be sold pursuant
to an effective registration statement or Rule 144 or such holder provides the
opinion with respect thereto described in clause (b) next above.

     5.2.  Transfer Agent Instructions.
           ---------------------------

           (a) The Company shall instruct its transfer agent to issue
certificates, registered in the name of the Purchaser or its nominee, for the
Shares of Series A Preferred Stock in accordance with the terms of this
Agreement, Conversion Shares and the Warrant Shares in such amounts as specified
from time to time by the Purchaser to the Company upon, and in accordance with
the terms of the Certificate of Designations or Common Stock Warrant, as the
case may be.  Such certificates shall bear a legend only in the form of the
Legend and only to the extent permitted by Section 5.1 above.  The Company
warrants that no instruction other than such instructions referred to in this
Article V, and no stop transfer instructions other than stop transfer
instructions to give effect to Section 2.6 hereof in the case of the Conversion
Shares and the Warrant Shares prior to registration under the Securities Act,
will be given by the Company to its transfer agent and, subject to applicable
law, the Securities shall otherwise be freely transferable on the books and
records of the Company.  Nothing in this Section shall affect in any way the
Purchaser's obligations and agreement set forth in Section 5.1 hereof to resell
the Securities pursuant to an effective registration statement and to deliver a
prospectus in connection with such sale or in compliance with an exemption from
the registration requirements of applicable securities laws.  Without limiting
any other rights of the Purchaser or obligations of the Company, if (i) the
Purchaser provides the Company with an opinion of counsel, to the effect that
the Securities to be sold or transferred may be sold or transferred pursuant to
an exemption from registration or (ii) the Purchaser transfers Securities
pursuant to Rule 144, the Company shall permit the transfer, and, in the case of
Conversion Shares and Warrant Shares promptly instruct its transfer agent to
issue one or more certificates in such name and in such denomination as
specified by the Purchaser in order to effect such a transfer or sale.

                                       21
<PAGE>

          (b) Purchaser shall exercise its right to convert the Shares of Series
A Preferred Stock or to exercise the Common Stock Warrant by faxing an executed
and completed Notice of Conversion or Form of Exercise Agreement to Purchase, as
applicable, to the Company, and delivering within two (2) business days
thereafter, the original Notice of Conversion (and the related certificates
representing the shares of Series A Preferred Stock, as applicable) or Form of
Exercise Agreement (and the related original Common Stock Warrant and exercise
price in the case of a non-cashless exercise of the Common Stock Warrant) to the
Company by hand delivery or by express courier, duly endorsed.  Each date on
which a Notice of Conversion or Form of Election to Purchase is faxed in
accordance with the provisions hereof shall be deemed a "Conversion Date."  The
                                                         ---------------
Company will transmit the certificates representing the Common Stock issuable
upon conversion of any shares of Series A Preferred Stock or upon exercise of
any Common Stock Warrant (together with the shares of Series A Preferred Stock
not so converted or the Stock Purchase Warrants not so exercised) to the
Purchaser via express courier as soon as practicable, but no later than in the
case of the conversion of Series A Preferred Stock, the later of (i) three (3)
business days after the Conversion Date or (ii) one (1) business day after
delivery of certificates representing the Series A Preferred Stock so converted,
and in the case of the exercise of the Common Stock Warrant no later than three
(3) business days after the Conversion Date (each such delivery date, together
with the Dividend Delivery Date referred to in paragraph (c) below, is referred
to herein as a "Delivery Date").  For purposes of this Agreement, any conversion
                -------------
of the Shares of Series A Preferred Stock and any exercise of the Common Stock
Warrant shall be deemed to have been made immediately prior to the close of
business on the Conversion Date.

          (c) If requested by the holder in the Notice of Conversion, the
Company will instruct its transfer agent to transmit the certificates
representing the Common Stock issuable in lieu of dividends payable on any
shares of Series A Preferred Stock to the Purchaser via express courier on the
Delivery Date applicable to the converted shares of Series A Preferred Stock.

          (d) In lieu of delivering physical certificates representing the
Common Stock issuable upon the conversion of, or in lieu of dividends on, the
Shares of Series A Preferred Stock or upon the exercise of the Common Stock
Warrant(s), provided the Company's transfer agent is participating in the
Depositary Trust Company ("DTC") Fast Automated Securities Transfer program, on
                           ---
the written request of the Purchaser, who shall have previously instructed the
Purchaser's prime broker to confirm such request to the Company's transfer
agent, the Company shall cause its transfer agent to electronically transmit
such Common Stock to the Purchaser by crediting the account of the Purchaser's
prime broker with DTC through its Deposit Withdrawal Agent Commission ("DWAC")
                                                                        ----
system no later than the applicable Delivery Date.

                                       22
<PAGE>

                                   ARTICLE VI
                 CONDITIONS TO THE COMPANY'S OBLIGATION TO SELL

     6.1.  Conditions to the Company's Obligation to Sell.  The obligation of
           ----------------------------------------------
the Company hereunder to issue and sell the Purchased Securities to the
Purchaser at the Closing is subject to the satisfaction, as of the date of such
Closing, of each of the following conditions thereto, 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:

           (a) The  Purchaser shall have executed this Agreement and the
Registration Rights Agreement and delivered the same to the Company.

           (b) The Purchaser shall deliver the Purchase Price in immediately
available funds for the Shares of Series A Preferred Stock and the Common Stock
Warrant.

           (c) The representations and warranties of the Purchaser shall be true
and correct as of the date when made and as of the Closing as though made at
that time, and each Purchaser shall have performed, satisfied and complied in
all material respects with the covenants and agreements required by this
Agreement to be performed or complied with by the Purchaser at or prior to the
Closing.

           (d) No statute, rule, regulation, executive order, decree, ruling or
injunction shall have been enacted, entered, promulgated or endorsed by any
court or governmental authority of competent jurisdiction or any self-regulatory
organization having authority over the matters contemplated hereby which
restricts or prohibits the consummation of any of the transactions contemplated
by this Agreement.

                                  ARTICLE VII
                CONDITIONS TO PURCHASER'S OBLIGATION TO PURCHASE

     7.1.  Conditions to the Closing.  The obligation of the Purchaser hereunder
           -------------------------
to purchase the Shares of Series A Preferred Stock and the Common Stock Warrant
to be purchased by it on the Closing Date is subject to the satisfaction of each
of the following conditions, provided that these conditions are for the
Purchaser's sole benefit and may be waived by the Purchaser at any time in the
Purchaser's sole discretion:

          (a) The Company shall have executed this Agreement, the Common Stock
Warrant and the Registration Rights Agreement and delivered the same to the
Purchaser.

          (b) The Company shall have delivered at the Closing one or more duly
executed certificate representing the Shares of Series A Preferred Stock, in
such denominations as the Purchaser shall request.

                                       23
<PAGE>

          (c) The Common Stock shall be designated for quotation and listed on
the Nasdaq National Market or the New York Stock Exchange and trading in the
Common Stock shall not have been suspended by the SEC or the Nasdaq National
Market or the New York Stock Exchange, as the case may be nor shall suspension
by the SEC or the Nasdaq National Market or the New York, Stock Exchange, as the
case may be, be threatened either in writing or by falling below the minimum
listing maintenance requirements of the Nasdaq National Market or New York Stock
Exchange, as the case may be and no de-listing or suspension shall be reasonably
likely in the judgment of the Purchaser for the foreseeable future.

          (d) The representations and warranties of the Company shall be true
and correct as of the date when made and as of the Closing (except for those
that address matters as of a particular date, which need only be true as of such
date) as though made at that time and the Company shall have performed,
satisfied and complied with the covenants and agreements required by this
Agreement to be performed or complied with by the Company at or prior to the
Closing, except where the breach of such representation, warranty or covenant
would not have a Material Adverse Effect.  The Purchaser shall have received a
certificate, executed by the Chief Executive Officer or Chief Financial Officer
of the Company, dated as of the Closing to the foregoing effect and as to such
other matters as may be reasonably requested by the Purchaser.

          (e) No statute, rule, regulation, executive order, decree, ruling or
injunction shall have been enacted, entered, promulgated or endorsed by any
court or governmental authority of competent jurisdiction or any self-regulatory
organization having authority over the matters contemplated hereby which
prohibits the consummation of any of the transactions contemplated by this
Agreement.

          (f) The Purchaser shall have received an opinion of the Company=s
counsel, dated as of the Closing, in the form attached hereto as Exhibit D.
                                                                 ---------

          (g) The Certificate of Designations shall have been accepted for
filing with the Secretary of State of the State of Delaware and a copies thereof
certified by the Secretary of State of Delaware shall have been delivered to
Purchaser and the Certificate of Incorporation and the Certificate of
Designations shall not have been amended, modified or rescinded after the date
of its filing and acceptance.

          (h) The Company shall have filed all notices, including, without
limitation, the application for listing of the Conversion Shares and the Warrant
Shares, as required under the rules of NASD or shall have obtained an effective
waiver of such requirements and the Conversion Shares and Warrant Shares shall
have been approved for listing, subject to official notice of issuance, on the
Nasdaq National Market.

          (i) On or prior to the Closing Date, there shall not have occurred any
of the following: (i) a suspension or material limitation in the trading of
securities generally on the Nasdaq National Market or the New York Stock
Exchange; (ii) a general moratorium on commercial banking activities in New York
declared by the applicable

                                       24
<PAGE>

banking authorities; (iii) the outbreak or escalation of hostilities involving
the United States, or the declaration by the United States of a national
emergency or war; or (iv) a change in international, political, financial or
economic conditions, if the effect of any such event, in the judgment of the
Purchaser, makes it impracticable or inadvisable to proceed with the purchase of
the shares of Series A Preferred Stock and the Common Stock Warrant on the terms
and in the manner contemplated in this Agreement and in the other Investment
Agreements.

          (j) On the Closing Date, the Company shall have reimbursed the
Purchaser for the Purchaser's Expenses incurred in connection with the
transactions contemplated by this Agreement (including reasonable fees and
disbursements of the Purchaser's legal counsel) as provided in Section 4.9
hereof.

          (k) On the Closing Date, the Purchaser shall have received a six month
lock-up agreement, dated the Closing Date, from Bathsheba J. Malsheen, Nicholas
Narlis, Eli Porat and David B. Levi in substantially the form as attached in
Exhibit E.
---------

          (l) Prior to the opening of  trading on the Nasdaq National Market on
August 11, 2000, the Company shall have issued a press release of its financial
results for the fourth quarter and fiscal year ended June 30, 2000.

                                 ARTICLE VIII
                         GOVERNING LAW; MISCELLANEOUS

     8.1.  Governing Law; Jurisdiction. This Agreement shall be governed by and
           ---------------------------
construed in accordance with the laws of the State of New York applicable to
contracts made and to be performed in the State of New York without regard to
choice of laws or conflict of laws principles thereof.  The parties hereto
irrevocably consent to the jurisdiction of the United States federal courts
located in the State of New York and the state courts located in the County of
New York in the State of New York in any suit or proceeding based on or arising
under this Agreement or the transactions contemplated hereby and irrevocably
agree that all claims in respect of such suit or proceeding may be determined in
such courts. The Company irrevocably waives the defense of an inconvenient forum
to the maintenance of such suit or proceeding. The Company further agrees that
service of process upon the Company mailed by the first class mail shall be
deemed in every respect effective service of process upon the Company in any
suit or proceeding arising hereunder. Nothing herein shall affect the
Purchaser=s right to serve process in any other manner permitted by law. The
parties hereto agree that a final non-appealable judgment in any such suit or
proceeding shall be conclusive and may be enforced in other jurisdictions by
suit on such judgment or in any other lawful manner.

     8.2.  Counterparts. This Agreement may be executed in two or more
           ------------
counterparts, including, without limitation, by facsimile transmission, all of
which counterparts 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. In the event any signature page is delivered by facsimile
transmission, the party using such

                                       25
<PAGE>

means of delivery shall cause additional original executed signature pages to be
promptly delivered to the other parties.

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

     8.4.  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 or the
validity or enforceability of this Agreement in any other jurisdiction.

     8.5.  Scope of Agreement; Amendments. This Agreement and the documents and
           ------------------------------
instruments referenced herein contain the entire understanding of the parties
with respect to the matters covered herein and therein.  No provision of this
Agreement may be waived other than by an instrument in writing signed by the
party to be charged with enforcement and no provision of this Agreement may be
amended other than by an instrument in writing signed by the Company and the
Purchaser.

     8.6.  Notice. Any notice herein required or permitted to be given under the
           ------
terms of this Agreement shall be in writing and may be personally served or
delivered by courier or by facsimile-machine confirmed telecopy, and shall be
deemed delivered at the time and date of receipt (which shall include telephone
line facsimile transmission).  The addresses for such communications shall be:

                    If to the Company:

                    VOXWARE, INC.
                    Lawrenceville Office Park
                    P.O. Box 5363
                    Princeton, New Jersey 08543
                    or
                    168 Franklin Corner Road
                    Suite 3
                    Lawrenceville, NJ 08648

                    Attn:  Nicholas Narlis
                    Telephone No.: (609) 514-4100
                    Facsimile No.: (609) 514-4101

                    with copies to:

                    Fulbright & Jaworski L.L.P.
                    666 Fifth Avenue
                    New York, N.Y. 10103

                    Attention: Paul Jacobs, Esq.

                                       26
<PAGE>

                    Telephone:  (212) 318-3000
                    Telecopy: (212) 318-3400

                    If to the Purchaser:

                    CASTLE CREEK TECHNOLOGY PARTNERS LLC
                    c/o Castle Creek Partners, LLC, Investment Manager
                    77 West Wacker Drive
                    Chicago, Illinois 60601

                    Attn:  Thomas A. Frei
                           Managing Director
                    Telephone No. (312) 499-6916
                    Facsimile No. (312) 499-6999

                    with copies to:

                    Wolf Block Schorr and Solis-Cohen LLP
                    1650 Arch Street - 22/nd/ Floor
                    Philadelphia, Pennsylvania  19103-2097

                    Attn:  Jason Shargel, Esq.
                    Telephone No.: (215) 977-2000
                    Facsimile No.: (215) 977-2334

     Each party shall provide notice to the other party of any change in
address.

     8.7.  Successors and Assigns. This Agreement shall be binding upon and
           ----------------------
inure to the benefit of the parties and their successors and assigns.  The
Company shall not assign this Agreement or any rights or obligations hereunder
without the prior written consent of the Purchaser.

     8.8.  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.

     8.9.  Survival.  The representations and warranties, covenants and
           --------
agreements in this Agreement shall survive the execution and delivery of this
Agreement and the Securities under the Investment Agreements, notwithstanding
any due diligence investigation conducted by or on behalf of the Purchaser. All
covenants and agreements of the Company in respect of which performance is
contemplated to occur following the Closing shall survive the Closing.
Notwithstanding the foregoing, except for the representations and warranties in
Section 3.1 and 3.3, all representations and warranties of the Company shall (a)
terminate and expire two years after the Closing, with respect to any claim
other than a tax claim, environmental claim or ERISA claim (as such terms are

                                       27
<PAGE>

hereafter defined); (b) terminate and expire with respect to any claim relating
to any inaccuracy in or any breach of representation or warranty of the Company
contained in Section 3.23 (a "tax claim") on the later of (i) the date upon
                              ---------
which the liability to which such tax claim may relate is barred by all
applicable statutes of limitations or (ii) the date upon which any claim for a
refund or credit related to such tax claim is barred by all applicable statutes
of limitations; (c) terminate and expire five (5) years after the Closing, with
respect to any claims or losses imposed under or pursuant to any safety or
environmental laws or principles of common law relating to pollution or
protecting the environment or concerning health or safety in connection with the
release of Hazardous Materials (an "environmental claim"); and (d) terminate and
                                    -------------------
expire with respect to any claim based upon or arising out of or otherwise in
respect of any inaccuracy in or any breach of representation or warranty of the
Company contained in Section 3.21 (an "ERISA claim") on the date upon which the
                                       -----------
liability to which such ERISA claim may relate is barred by all applicable
statutes of limitation.  The Company agrees to indemnify and hold harmless the
Purchaser and each of the Purchaser=s officers, directors, members, managers,
employees, partners, agents and affiliates and any direct or indirect officers,
directors, shareholders, members, managers, employees, partners, agents and
affiliates of any of the foregoing for loss or damage arising as a result of or
related to (a) any breach by the Company of any of its representations,
warranties, covenants and agreements set forth herein, or (b) any cause of
action, suit or claim brought or made against such indemnitee, other than
directly by the Company solely for breach of this Agreement, the Common Stock
Warrant, the Series A Preferred Stock or the Registration Rights Agreement by
the indemnitee or by governmental or regulatory authorities, and arising out of
or resulting from (whether in whole or in part) the execution, delivery,
performance by the Company or enforcement of this Agreement or any other
Investment Agreements or any other instrument, document or agreement executed
pursuant hereto or thereto or contemplated hereby or thereby (including without
limitation the acquisition of the Series A Preferred Stock, the Common Stock
Warrant, the Convertible Shares, and/or the Warrant Shares), any transaction
financed or to be financed in whole or in part, directly or indirectly, with the
proceeds of the issuance of the Securities or the status of the Purchaser as an
investor in the Company, except to the extent that such actual loss or damage
directly results from a breach by such indemnitee of this Agreement, the Common
Stock Warrant, or the Registration Rights Agreement or from a violation of law
or gross negligence or willful misconduct; provided, that, indemnification under
the Registration Rights Agreement shall be governed by and construed in
accordance with such agreement.  The right to indemnification shall include the
right to advancement of expenses as they are incurred; provided, however, that
any expenses so advanced shall be returned in the event a final nonappealable
judgment is rendered by a court of competent jurisdiction to the effect that
such indemnification is not required under the terms of this Agreement or
permitted under applicable law.  Notwithstanding the foregoing, the Company
shall not be required to indemnify and hold harmless any person for any loss
occasioned by a limitation set forth in the Certificate of Designation or Common
Stock Warrant on the Company's ability to issue Conversion Shares or Warrant
Shares in excess of the Exchange Cap.

                                       28
<PAGE>

     8.10.  Public Filings; Publicity. On the same day as the Company files the
            -------------------------
Form 8-K required pursuant to Section 4.2, the Company shall issue a press
release with respect to the transactions contemplated hereby. The Company and
the Purchaser shall have the right to review reasonably in advance of the
issuance any press releases (including the foregoing press release), SEC or
other filings, or any other public statements, with respect to the transactions
contemplated hereby; provided, however, that the Company shall be entitled,
without the prior approval of the Purchaser, to make any press release or SEC,
Nasdaq, NASD or exchange filings with respect to such transactions as is
required by applicable law and regulations (although the Purchaser shall (to the
extent time permits) be consulted by the Company in connection with any such
press release prior to its release and shall be provided with a copy thereof).

     8.11.  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.

     8.12.  Remedies, Characterizations, Other Obligations, Breaches and
            ------------------------------------------------------------
Injunctive Relief.  The remedies provided in this Agreement shall be cumulative
-----------------
and in addition to all other remedies available under this Agreement, at law or
in equity (including a decree of specific performance and/or other injunctive
relief), no remedy contained herein shall be deemed a waiver of compliance with
the provisions giving rise to such remedy and nothing herein shall limit a
Purchaser's right to actual damages for any failure by the Company to comply
with the terms of this Agreement. Amounts set forth or provided for herein with
respect to payments and the like (and the computation thereof) shall be the
amounts to be received by the Purchaser and shall not, except as expressly
provided herein, be subject to any other obligation of the Company (or the
performance thereof).

     8.13.  Failure or Indulgence Not Waiver.  No failure or delay on the part
            --------------------------------
of a Purchaser in the exercise of any power, right or privilege hereunder shall
operate as a waiver thereof, nor shall any single or partial exercise of any
such power, right or privilege preclude other or further exercise thereof or of
any other right, power or privilege.

     8.14.  Termination.  In the event that the Closing shall not have occurred
            -----------
on August 14, 2000, time being of the essence, unless the parties agree
otherwise, this Agreement shall terminate at the close of business on such date.
Notwithstanding any termination of this Agreement, any party not in breach of
this Agreement shall preserve all rights and remedies it may have against the
other party hereto for a breach of this Agreement prior to or relating to the
termination.

     8.15.  Joint Participation in Drafting.  Each party to this Agreement and
            -------------------------------
to the Investment Agreements has participated in the drafting of such
Agreements.  As such, the language used herein and therein shall be deemed to be
the language chosen by the

                                       29
<PAGE>

parties hereto to express their mutual intent and no rule of strict construction
shall be applied against any party to this Agreement.

                    [REMAINDER OF PAGE INTENTIONALLY BLANK]

                                       30
<PAGE>

     IN WITNESS WHEREOF, the undersigned Purchaser and the Company have caused
this Agreement to be duly executed as of the date first above written.

     COMPANY:

     VOXWARE, INC.

     By: /s/ Nicholas Narlis
         -------------------
     Name:   Nicholas Narlis
     Title:  Senior Vice President and Chief Financial Officer

     PURCHASER:

     CASTLE CREEK TECHNOLOGY PARTNERS LLC

     By:  Castle Creek Partners, L.L.C.
     Its: Investment Manager

     By:  /s/ Michael L. Spolan
          ----------------------
     Name:    Michael L. Spolan
     Title:   Managing Director

     Address:  77 West Wacker Drive
               Suite 4040
               Chicago, Illinois 60601
               Telephone: 312-499-6900

     Copy to:

               Wolf, Block, Schorr and Solis-Cohen LLP
               1650 Arch Street - 22/nd/ Floor
               Philadelphia, Pennsylvania 19103-2097
               Attn.: Jason Shargel, Esq.
               Facsimile: (215) 977-2334

                                       31<PAGE>

                                                                    EXHIBIT 10.2

                         REGISTRATION RIGHTS AGREEMENT

     THIS REGISTRATION RIGHTS AGREEMENT (this "Agreement"), is made as of August
                                               ---------
15, 2000, by and among VOXWARE, Inc., a Delaware corporation (the "Company"),
                                                                   -------
with principal executive office located at 168 Franklin Corner Road, Suite 3,
Lawrenceville, New Jersey 08543, and the undersigned (the " Purchaser").
                                                            ---------

                                   RECITALS
                                   --------

     A.   In connection with the Securities Purchase Agreement dated as of
August 10, 2000 by and between the Company and the Purchaser (the "Securities
                                                                   ----------
Purchase Agreement"), the Company has agreed, upon the terms and subject to the
------------------
conditions contained therein, to issue and sell to the Purchaser (i) an amount
of the Company's Series A Convertible Preferred Stock (the "Preferred Stock")
                                                            ---------------
which is convertible into shares of the Company's Common Stock, $0.001 par value
(the "Common Stock") and (ii) a warrant (the "Common Stock Warrant") entitling
      ------------                            --------------------
the holder thereof to purchase the number of shares (the "Warrant Shares") of
                                                          --------------
Common Stock as set forth therein.   The shares of Common Stock issuable upon
conversion of or otherwise pursuant to the Preferred Stock are referred to
herein as the "Conversion Shares." The Preferred Stock, the Common Stock
               -----------------
Warrants, the Conversion Shares and the Warrant Shares are collectively referred
to herein as the "Securities".
                  ----------

     B.   To induce the Purchaser to execute and deliver the Securities Purchase
Agreement, the Company has agreed to provide certain registration rights under
the Securities Act of 1933, as amended, and the rules and regulations
thereunder, or any similar successor statute (collectively, the "Securities
                                                                 ----------
Act"), and applicable state securities laws.
---
                                  AGREEMENTS
                                  ----------

     NOW THEREFORE, in consideration of the premises and the mutual covenants
contained herein and other good and valuable consideration, the receipt and
sufficiency of which are hereby acknowledged, the Company and the Purchaser
hereby agree as follows:

                                   ARTICLE I
                                  DEFINITIONS
                                  -----------

     1.1  Definitions.  As used in this Agreement, the following terms shall
          -----------
have the following meanings:
<PAGE>

          (a)  "Holder" means the Purchaser and any transferees or assignees who
                ------
agree to become bound by the provisions of this Agreement in accordance with
Article IX hereof.

          (b)  "register," "registered," and "registration" refer to a
                --------    ----------        ------------
registration effected by preparing and filing a Registration Statement or
Statements in compliance with the Securities Act and pursuant to Rule 415 under
the Securities Act or any successor rule providing for offering securities on a
continuous basis ("Rule 415"), and the declaration or ordering of effectiveness
                   --------
of such Registration Statement by the United States Securities and Exchange
Commission (the "SEC").
                 ---

          (c)  "Registrable Securities" means the Conversion Shares (including
                ----------------------
any Conversion Shares issuable with respect to dividends or other payments under
the terms of the Preferred Stock and the Securities Purchase Agreement) issued
or issuable with respect to the Preferred Stock, the Warrant Shares (without
regard to any limitations on conversion or exercise) and any shares of capital
stock or other securities issued or issuable, from time to time (with any
adjustments), on or in exchange for or otherwise with respect to the Common
Stock or any other Registrable Securities.

          (d)  "Registration Statement" means a registration statement of the
                ----------------------
Company under the Securities Act pursuant to the provisions of this Agreement.

     1.2  Capitalized Terms.  Capitalized terms used herein and not otherwise
          -----------------
defined herein shall have the respective meanings set forth in the Securities
Purchase Agreement.

                                  ARTICLE II
                                 REGISTRATION
                                 ------------

     2.1  Mandatory Registration. The Company shall prepare and file as soon as
          ----------------------
practicable, but in any event on or prior to August 31, 2000 (the "Filing
                                                                   ------
Deadline") with the SEC a Registration Statement on Form S-3 covering the resale
--------
of all of the Registrable Securities issuable upon full conversion of the
Preferred Stock and full exercise of the Common Stock Warrant purchased and sold
at the Closing, without regard to any limitation on any conversion or exercise,
provided that, for purposes of the initial filing of such Registration
Statement, the amount registered shall equal the sum of  (i) the number of
shares of Common Stock constituting the Exchange Cap (as defined in the
Certificate of Designations governing the Preferred Stock) and (ii) the number
of shares of Common Stock initially issuable upon exercise of the Common Stock
Warrant (in each case, without regard to any limitations upon exercise or
conversion thereupon).  The Registration Statement may also register the resale
of (i) 325,000 shares of Common Stock held by or issuable to Inroad, Inc. in
connection with the Inroad Acquisition (as defined in the Securities Purchase
Agreement) and (ii) 50,000 shares of Common Stock issuable to Stratos Product
Development, LLC pursuant to the  Stratos Warrants (as defined in the Securities
Purchase Agreement), to the extent that Inroad, Inc. and Stratos Product
Development, LLC are currently entitled to require the Company to register their
shares of Common Stock pursuant to a registration rights agreement.  The
Registration Statement (and each amendment or supplement thereto, and each
request for acceleration of effectiveness

                                       2
<PAGE>

thereof) shall be provided to the Holders and their counsel for review prior to
filing. If the Holders and their counsel do not approve such documents within
five (5) Business Days, the Registration Deadline (as set forth in Section 2.3)
shall be extended by the number of Business Days that elapse after the fifth
Business Day following the submission of such documents to the Holders and their
counsel for review and before such approval is granted. The Company shall also
prepare and file such amendments to registration statements and such additional
registration statements as may from time to time be required by this Agreement.
If the Registration Statement is not filed by the Filing Deadline, the Company
shall thereafter continue to use its best efforts to cause such Registration
Statement to be filed as promptly as practicable.

     2.2  Underwritten Offering.  If any offering pursuant to a Registration
          ---------------------
Statement pursuant to Section 2.1 hereof involves an underwritten offering, the
Holders of a majority of the Registrable Shares to be registered pursuant to
such Registration Statement shall have the right to select legal counsel to
represent it and an investment banker or bankers and manager or managers to
administer the offering, which investment banker or bankers or manager or
managers shall be reasonably satisfactory to the Company.

     2.3  Payments by the Company. The Company shall use its best efforts to
          -----------------------
cause each Registration Statement required to be filed pursuant to Section 2.1
hereof to become effective as soon as practicable, but in no event later than
the ninetieth (90th) day (one hundred twenty (120) days if reviewed in writing
by the SEC) following the Closing Date.  If such Registration Statement is not
effective by the 90th day (or 120th day, if applicable) following the Closing
Date, the Company shall thereafter continue to use its best efforts to cause
such Registration Statement to become effective as soon as practicable. If a
Registration Statement covering the Registrable Securities required to be filed
by the Company pursuant to Section 2.1 hereof is not filed with the SEC on or
before the Filing Deadline or declared effective by the SEC on or before the
applicable Registration Deadline (as defined herein) (a "Registration Failure"),
                                                         --------------------
or if after such Registration Statement has been declared effective by the SEC,
sales of all the Registrable Securities covered thereby cannot be made pursuant
to such Registration Statement (by reason of a stop order, the Company's failure
to update the registration statement, the failure of any post-effective
amendment to the registration statement to be promptly declared effective or any
other reason outside the control of the Holders) (a "Registration Suspension"),
                                                     -----------------------
then the Company will make payments to the Holders in such amounts and at such
times as shall be determined pursuant to this Section 2.3 as partial relief for
the damages to the Holders by reason of any such delay in or reduction of their
ability to sell the Registrable Securities (which remedy shall not be exclusive
of any other remedies available at law or in equity).  For purposes hereof, the
"Registration Deadline" shall mean the ninetieth (90th) day following the
 ---------------------
Closing Date or, if the SEC reviews such Registration Statement, the one hundred
twentieth (120th) day following the Closing Date.  In the event of a
Registration Failure occasioned by the failure to file the Registration
Statement (or, if applicable an amendment thereto) required to be filed pursuant
to Section 2.1 or Section 3.2 on or before the Filing Deadline (or, if
applicable, the Additional Filing Deadline) the Company shall pay the Holders an
amount equal to (A) the Multiplier (as defined) times (B) the Funded Amount (as
                                                -----
defined below) times (C) the number of months (prorated per day for partial
               -----
months) following the Filing Deadline (or, if applicable, the Additional Filing
Deadline) and

                                       3
<PAGE>

prior to the date the applicable Registration Statement required (or, if
applicable, amendment thereto) is filed with the SEC. In the event of a
Registration Failure occasioned by the failure of the Registration Statement to
be declared effective by the SEC on or before the applicable Registration
Deadline, the Company shall pay to the Holders an amount equal to (D) the
Multiplier times (E) the Funded Amount times (F) the number of months (prorated
           -----                       -----
per day for partial months) following the applicable Registration Deadline and
prior to the date the applicable Registration Statement (or, if applicable,
amendment thereto) is declared effective by the SEC. In addition, in the event
of a Registration Suspension, the Company shall pay to the Holders an amount
equal to (G) the Multiplier times (H) the Funded Amount times (i) the number of
                            -----
months (prorated per day for partial months) from (x) the date on which sales of
all the Registrable Securities first cannot be made to (y) the date on which
sales of all such Registrable Securities can again be made. Amounts to be paid
pursuant to this Section 2.3 shall be paid pro rata to Holders based upon the
number of Conversion Shares and Warrant Shares owned by them (including, for
these purposes, Conversion Shares issuable upon full conversion of the Preferred
Stock and Warrant Shares issuable upon full exercise of the Warrant by each
Holder, in each case without regard to any limitations upon exercise and
conversion contained therein) and shall be paid in cash.  Such payments shall
be made within five (5) days after the end of each period that gives rise to
such obligation, provided that, if any such period extends for more than thirty
(30) days, payments shall be made for each such thirty (30) day period within
five (5) days after the end of such thirty (30) day period.  For any given date
the "Multiplier" shall mean, (i) during the first thirty (30) days following the
     ----------
Filing Deadline, Additional Filing Deadline and/or the Registration Deadline, as
applicable, during which there is a Registration Failure or Registration
Suspension, one percent (1%),(ii) during the second thirty (30) days following
the applicable Registration Failure, one and one-half per cent (1-1/2 %); and
(iii) after the sixtieth (60) day of a Registration Failure or Registration
Suspension, two percent (2%).  With respect to any given Registration Statement,
the "Funded Amount" means the aggregate purchase price of the Preferred Stock
     -------------
and the Warrant relating to the Common Stock registered (or to be registered) on
such Registration Statement.

     2.4  Piggy-Back Registrations.  If at any time prior to the expiration of
          ------------------------
the Registration Period (as hereinafter defined) the Company shall file with the
SEC a Registration Statement relating to an offering for its own account or the
account of others under the Securities Act of any of its equity securities
(other than on Form S-4 or Form S-8 or their then equivalents relating to equity
securities to be issued solely in connection with any acquisition of any entity
or business or equity securities issuable in connection with stock option or
other employee benefit plans), then the Company shall send to the Holders
written notice of such determination and, if within fifteen (15) days after the
date of such notice, the Holders shall so request in writing, the Company shall
include in such Registration Statement all or any part of the Registrable
Securities such Holder requests to be registered, except that if, in connection
with any underwritten public offering for the account of the Company the
managing underwriter(s) thereof shall impose a limitation on the number of
shares of Common Stock which may be included in the Registration Statement
because, in such underwriter(s)' judgment, marketing or other factors dictate
such limitation is necessary to facilitate public distribution, then the Company
shall be obligated to include in such Registration Statement only such limited
portion of the Registrable Securities with respect to which the Holders has
requested inclusion hereunder as the underwriter shall permit.  Any exclusion of
Registrable Securities

                                       4
<PAGE>

shall be made pro rata among the Holders seeking to include Registrable
Securities, in proportion to the number of Registrable Securities sought to be
included by such Holder; provided, however, that the Company shall not exclude
any Registrable Securities unless the Company has first excluded all outstanding
securities, the holders of which are not entitled to inclusion of such
securities in such Registration Statement or are not entitled to pro rata
inclusion with the Registrable Securities; and provided, further, however, that,
after giving effect to the immediately preceding proviso, any exclusion of
Registrable Securities shall be made pro rata with holders of other securities
having the right to include such securities in the Registration Statement. No
right to registration of Registrable Securities under this Section 2.4 shall be
construed to limit any registration required under Section 2.1 or 3.2 hereof. If
an offering in connection with which a Holder is entitled to registration under
this Section 2.4 is an underwritten offering, then each Holder whose Registrable
Securities are included in such Registration Statement shall, unless otherwise
agreed by the Company, offer and sell such Registrable Securities in an
underwritten offering using the same underwriter or underwriters and, subject to
the provisions of this Agreement, on the same terms and conditions as other
shares of Common Stock included in such underwritten offering. So long as any
other Registration Statement is effective and immediately available for use so
that all of the Registrable Securities may be sold in reliance thereon, the
provisions of this Section shall not apply.

     2.5  Eligibility for Form S-3.  The Company represents and warrants that it
          ------------------------
is currently eligible to register the resale of the Conversion Shares, Warrant
Shares and all Registrable Securities by the Holders on a Registration Statement
on Forms S-3 under the Securities Act for the account of Holders (and not for or
on behalf of Company).  The Company shall file all reports required to be filed
by the Company with the SEC in a timely manner and take all other actions which
may be required so as to maintain such eligibility for the use of Forms S-3.

                                  ARTICLE III
                          OBLIGATIONS OF THE COMPANY
                          --------------------------

     In connection with the registration of the Registrable Securities, the
Company shall have the following obligations, including with respect to each
Registration Statement required to be filed hereunder:

     3.1  The Company shall prepare promptly and file with the SEC the
Registration Statement required by Section 2.1, and cause such Registration
Statement relating to Registrable Securities to become effective as soon as
practicable after such filing, and keep the Registration Statement effective
pursuant to Rule 415 and immediately available for use at all times until such
date as is the earlier of (i) the date on which all of the Registrable
Securities have been sold (and no further Registrable Securities may be issued
in the future) and (ii) the date on which all of the Registrable Securities (in
the reasonable opinion of counsel to the Holders) may be immediately sold to the
public without registration and without restriction as to the number of
Registrable Securities to be sold pursuant to Rule 144 (k) or any successor
provision (the "Registration Period").  The Registration Statement (including
                -------------------
any amendments or supplements thereto and prospectuses contained therein and all
documents incorporated by reference therein) shall not contain any untrue
statement of a material

                                       5
<PAGE>

fact or omit to state a material fact required to be stated therein, or
necessary to make the statements therein not misleading.

     3.2  The Company shall prepare and file with the SEC such amendments
(including post-effective amendments) and supplements to a Registration
Statement and the prospectus used in connection with the Registration Statement
as may be necessary to keep the Registration Statement effective and immediately
available for use at all times during the Registration Period, and, during such
period, comply with the provisions of the Securities Act with respect to the
disposition of all Registrable Securities of the Company covered by the
Registration Statement until the termination of the Registration Period or, if
earlier, such time as all of such Registrable Securities have been disposed of
in accordance with the intended methods of disposition by the seller or sellers
thereof as set forth in the Registration Statement.  In the event the number of
shares available under a Registration Statement filed pursuant to this Agreement
is, at any time, insufficient to cover one hundred seventy-five percent (175%)
of the Registrable Securities issued or issuable upon conversion of the
Preferred Stock and upon exercise of the Warrant (in each case, without giving
effect to any limitation on conversion or exercise thereof) held by any Holder
and required to be covered by such Registration Statement pursuant to Section
2.1 or Section 3.2 hereof, the Company shall amend, if permissible,  the
Registration Statement, or file a new Registration Statement (on the short form
available therefor, if applicable), or both, so as to cover two hundred percent
(200%) of the Registrable Securities issued or issuable to such Holder upon such
exercise or conversion (in each case, without giving effect to any limitation on
conversion or exercise thereof), in each case, as soon as practicable, but in
any event within five (5) days (the "Additional Filing Deadline").  The Company
                                     --------------------------
shall cause such amendment and/or new Registration Statement to become effective
as soon as practicable following the filing thereof, but in any event within ten
(10) Business Days with respect to an amendment and ten (10) Business Days with
respect to a new Registration Statement (or within 75 days after the filing of
such amendment or new Registration Statement, if reviewed in writing by the SEC)
(each such deadline also being a "Registration Deadline").
                                  ---------------------

     3.3  The Company shall furnish to each Holder whose Registrable Securities
are included in the Registration Statement and its legal counsel (a) promptly
after the same is prepared and publicly distributed, filed with the SEC, or
received by the Company, one copy of the Registration Statement and any
amendment thereto, each preliminary prospectus and prospectus and each amendment
or supplement thereto, and, in the case of the Registration Statement referred
to in Section 2.1, each letter written by or on behalf of the Company to the SEC
or the staff of the SEC, and each item of correspondence from the SEC or the
staff of the SEC, in each case relating to such Registration Statement (other
than any portion, if any, thereof which contains information for which the
Company has sought confidential treatment), and (b) such number of copies of a
prospectus, including a preliminary prospectus, and all amendments and
supplements thereto and such other documents as such Holder may reasonably
request in order to facilitate the disposition of the Registrable Securities
owned (or to be owned) by such Holder.

     3.4  The Company shall (a) register and qualify the Registrable Securities
covered by the Registration Statement under securities laws of such
jurisdictions in the United States as each Holder

                                       6
<PAGE>

who holds (or has the right to hold) Registrable Securities being offered
reasonably requests, (b) prepare and file in those jurisdictions such amendments
(including post-effective amendments) and supplements to such registrations and
qualifications as may be necessary to maintain the effectiveness thereof and
availability for use during the Registration Period, (c) take such other actions
as may be necessary to maintain such registrations and qualifications in effect
at all times during the Registration Period, and (d) take all other actions
reasonably necessary or advisable to qualify the Registrable Securities for sale
in such jurisdictions; provided, however, that the Company shall not be required
in connection therewith or as a condition thereto to (i) qualify to do business
in any jurisdiction where it would not otherwise be required to qualify but for
this Section 3.4, (ii) subject itself to general taxation in any such
jurisdiction, (iii) file a general consent to service of process in any such
jurisdiction, (iv) make any change in its charter or by-laws, which in each case
the board of directors of the Company determines to be contrary to the best
interests of the Company and its stockholders.

     3.5  In the event the Holders in an offering pursuant to a Registration
Statement or any amendment or supplement thereto under Section 2.1 or Section
3.2 hereof  elect underwriters for the offering, as provided in Section 2.2
hereof, the Company shall enter into and perform its obligations under an
underwriting agreement, in usual and customary form, including, without
limitation, customary indemnification and contribution obligations, with the
underwriters of such offering.

     3.6  As soon as practicable after becoming aware of such event, the Company
shall notify (by telephone and also by facsimile and reputable overnight
courier) each Holder of the happening of any event, of which the Company has
knowledge, as a result of which the prospectus included in the Registration
Statement, as then in effect, includes an untrue statement of a material fact or
omission to state a material fact required to be stated therein or necessary to
make the statements therein not misleading, and use its best efforts as soon as
possible (but in any event within five (5) days) to prepare a supplement or
amendment to the Registration Statement (and make all required filings with the
SEC) to correct such untrue statement or omission, and the Company shall
simultaneously (and thereafter as requested) deliver such number of copies of
such supplement or amendment (or other applicable document) to each Holder as
such Holder may request in writing.

     3.7  The Company shall use commercially reasonable efforts to prevent the
issuance of any stop order or other suspension of effectiveness of a
Registration Statement, and, if such an order is issued, to obtain the
withdrawal of such order at the earliest practicable time and the Company shall
immediately notify by facsimile each Holder (at the facsimile number for such
Holder set forth on the signature page hereto) who holds Registrable Securities
being sold (or, in the event of an underwritten offering, the managing
underwriters) of the issuance of such order and the resolution thereof.

     3.8  The Company shall make generally available to its security holders as
soon as practical, but not later than ninety (90) days after the close of the
period covered thereby, an earnings statement (in form complying with the
provisions of Rule 158 under the Securities Act) covering a twelve-month period
beginning not later than the first day of the Company's fiscal quarter next
following the effective date of the Registration Statement.

                                       7
<PAGE>

     3.9  At the request of any Holder, the Company shall furnish, on the date
of effectiveness of the Registration Statement and thereafter from time to time
on such dates as a Holder may reasonably request (a) an opinion, dated as of
such applicable date, from counsel representing the Company addressed to the
Holder and in form, scope and substance as is customarily given in an
underwritten public offering and (b) a letter, dated as of such applicable date,
from the Company's independent certified public accountants addressed to the
Holder and in form, scope and substance as customarily given to underwriters in
an underwritten public offering.

     3.10 The Company shall make available for inspection by (i) any Holder,
(ii) any underwriter participating in any disposition pursuant to the
Registration Statement, (iii) attorneys and accountants retained by any Holder,
and (iv) attorneys retained by such underwriters (collectively, the
"Inspectors") all pertinent financial and other records, and pertinent corporate
 ----------
documents and properties of the Company (collectively, the "Records"), as shall
                                                            -------
be reasonably deemed necessary by each Inspector and cause the Company's
officers, directors and employees to supply all information which any Inspector
may reasonably request; provided, however, that each Inspector shall hold in
confidence and shall not make any disclosure (except to a Holder) of any Record
or other information which the Company determines in good faith to be
confidential, and of which determination the Inspectors are so notified in
writing, unless (a) the disclosure of such Records is necessary to avoid or
correct a misstatement or omission in any Registration Statement or is otherwise
required to be disclosed in such Registration Statement to permit Holder to sell
under such Registration Statement, (b) the release of such Records is ordered
pursuant to a subpoena or other order from a court or government body of
competent jurisdiction, or is otherwise required by applicable law or legal
process or (c) the information in such Records has been made generally available
to the public other than by disclosure in violation of this or any other
agreement (to the knowledge of the relevant Holder).  The Company shall not be
required to disclose any confidential information in such Records to any
Inspector or Holder until and unless such Inspector shall have entered into
confidentiality agreements (in form and reasonable substance satisfactory to the
Company) with the Company with respect thereto, substantially in the form of
this Section 3.11.  Each Holder agrees that it shall, upon learning that
disclosure of such Records is sought in or by a court or governmental body of
competent jurisdiction or through other means, give prompt notice to the Company
and allow the Company, at its expense, to undertake appropriate action to
prevent disclosure of, or to obtain a protective order for, the Records deemed
confidential.  Nothing herein shall be deemed to limit a Holder's ability to
sell Registrable Securities in a manner which is consistent with applicable laws
and regulations.

     3.11 The Company shall hold in confidence and not make any disclosure of
information concerning a Holder provided to the Company unless (a) disclosure of
such information is necessary to comply with federal or state securities laws,
(b) the disclosure of such information is necessary to avoid or correct a
misstatement or omission in any Registration Statement, (c) the release of such
information is ordered pursuant to a subpoena or other order from a court or
governmental body of competent jurisdiction or is otherwise required by
applicable law or legal process, (d) such information has been made generally
available to the public other than by disclosure in violation of this or any
other agreement (to the knowledge of the Company), or (e) such Holder consents
to the

                                       8
<PAGE>

form and content of any such disclosure. The Company agrees that it shall, upon
learning that disclosure of such information concerning a Holder is sought in or
by a court or governmental body of competent jurisdiction or through other
means, give prompt notice to such Holder prior to making such disclosure, and
allow the Holder, at its expense, to undertake appropriate action to prevent
disclosure of, or to obtain a protective order for, such information.

     3.12  From and after Closing, the Company shall cause the listing and the
continuation of listing of all the Registrable Securities on the Nasdaq Market
or the New York Stock Exchange, and cause the Registrable Securities to be
quoted or listed on each additional national securities exchange or quotation
system upon which the Common Stock is then listed or quoted.

     3.13  The Company shall provide a transfer agent and registrar, which may
be a single entity, for the Registrable Securities not later than the effective
date of the Registration Statement.

     3.14  The Company shall cooperate with the Holders who hold Registrable
Securities being offered and the managing underwriter or underwriters, if any,
to facilitate the timely preparation and delivery of certificates (not bearing
any restrictive legends) representing Registrable Securities to be offered
pursuant to the Registration Statement and enable such certificates to be in
such denominations or amounts, as the case may be, as the managing underwriter
or underwriters, if any, or the Holder may reasonably request and registered in
such names as the managing underwriter or underwriters, if any, or the Holder
may request, and, within one (1) business day after a Registration Statement
which includes Registrable Securities is ordered effective by the SEC, the
Company shall cause legal counsel selected by the Company to deliver, to the
transfer agent for the Registrable Securities (with copies to the Holders whose
Registrable Securities are included in such Registration Statement) an opinion
of such counsel in the form attached hereto as Exhibit 1.
                                               ---------

     3.15  At the request of any Holder, the Company shall promptly prepare and
file with the SEC such amendments (including post-effective amendments) and
supplements to a Registration Statement and the prospectus used in connection
with the Registration Statement as may be necessary in order to change the plan
of distribution set forth in such Registration Statement.

     3.16  The Company shall comply with all applicable laws related to a
Registration Statement and offering and sale of securities covered by the
Registration Statement and all applicable rules and regulations of governmental
authorities in connection therewith (including, without limitation, the
Securities Act and the Exchange Act and the rules and regulations promulgated by
the Commission).

     3.17  The Company shall take all such other actions as any Holder or the
underwriters, if any, reasonably request in order to expedite or facilitate the
disposition of such Registrable Securities.

     3.18  From and after the date of this Agreement,  the Company shall not,
and shall not agree to, allow the holders of any securities of the Company
(other than Holders with respect to Registrable Securities and except as
otherwise as provided in Section 2.1 hereof,) to include any of their securities

                                       9
<PAGE>

in any Registration Statement or any amendment or supplement thereto under
Section 2.1 or 3.2 hereof without the consent of the Holders of a majority of
the outstanding Registrable Securities.

     3.19  The Registration Statement shall state that it covers such
indeterminate number of additional shares as may be issuable upon conversion of
the Preferred Stock or exercise of the Common Stock Warrant to prevent dilution
resulting from stock splits, stock dividends and other similar transactions.

                                  ARTICLE IV
                         OBLIGATIONS OF THE HOLDER(S)
                         ----------------------------

     In connection with the registration of the Registrable Securities, each
Holder shall have the following obligations:

     4.1  Each Holder shall furnish to the Company such information regarding
itself, the Registrable Securities held by it and the intended method of
disposition of the Registrable Securities held by it as shall be required to
effect the registration of such Registrable Securities. At least five (5)
business days prior to the first anticipated filing date of the Registration
Statement, the Company shall notify each Holder of the information the Company
requires from each such Holder.

     4.2  Each Holder, by such Holder's acceptance of the Registrable
Securities, agrees to cooperate with the Company as reasonably requested by the
Company in connection with the preparation and filing of the Registration
Statements hereunder, unless such Holder has notified the Company in writing of
such Holder's election to exclude all of such Holder's Registrable Securities
from the Registration Statement.

     4.3  Each Holder whose Registrable Securities are included in a
Registration Statement understands that the Securities Act may require delivery
of a prospectus relating thereto in connection with any sale thereof pursuant to
such Registration Statement, and each such Holder shall use its reasonable
efforts to comply with the applicable prospectus delivery requirements of the
Securities Act in connection with any such sale.

     4.4  Each Holder agrees that, upon receipt of written notice from the
Company of the happening of any event of the kind described in Section 3.6, such
Holder will immediately discontinue disposition of Registrable Securities
pursuant to the Registration Statement covering such Registrable Securities
until such Holder's receipt of the copies of the supplemented or amended
prospectus contemplated by Section 3.6 or advice that a supplement or amendment
is not required and, if so directed by the Company, such Holder shall deliver to
the Company (at the expense of the Company) or destroy (and deliver to the
Company a certificate of destruction) all copies in such Holder's possession
(other than a limited number of permanent file copies), of the prospectus
covering such Registrable Securities current at the time of receipt of such
notice. Holder's obligations under this paragraph shall in no way limit the
Company's obligations under this Agreement or Holder's rights or

                                       10
<PAGE>

remedies against the Company with respect to any breach or threatened breach by
the Company of any such obligations.

     4.5  Without limiting a Holder's rights under Section 2.1 or 3.2 hereof, no
Holder may participate in any underwritten distribution hereunder unless such
Holder (a) agrees to sell such Holder's Registrable Securities on the basis
provided in any underwriting agreements in usual and customary form entered into
by the Company pursuant to Section 3.5 hereof, (b) completes and executes all
questionnaires, powers of attorney, indemnities, underwriting agreements and
other documents reasonably required under the terms of such underwriting
arrangements, and (c) agrees to pay its pro rata share of all underwriting
discounts and commissions and any expenses in excess of those payable by the
Company pursuant to Article V. Without implication that the contrary would
otherwise be true, it is expressly understood and agreed that no Holder shall be
required to participate in any such underwritten distribution.

                                   ARTICLE V
                           EXPENSES OF REGISTRATION
                           ------------------------

     All expenses, other than underwriting discounts and commissions, incurred
in connection with registrations, filings or qualifications pursuant to Articles
II and III, including, without limitation, all registration, listing and
qualification fees, printers and accounting fees, the fees and disbursements of
counsel for the Company and of one counsel for the Holders.

                                  ARTICLE VI
                                INDEMNIFICATION
                                ---------------

     In the event any Registrable Securities are included in a Registration
Statement under this Agreement:

     6.1  To the extent permitted by law, the Company will indemnify, hold
harmless and defend (a) each Holder who holds such Registrable Securities, (b)
each underwriter of Registrable Securities and (c) the directors, officers,
partners, members, employees, agents and persons who control any Holder within
the meaning of Section 15 of the Securities "ct or Section 20 of the Exchange
Act, if any, (each, an "Indemnified Person"), against any losses, claims,
                        ------------------
damages, liabilities or expenses (collectively, together with actions,
proceedings or inquiries whether or not in any court, before any administrative
body or by any regulatory or self-regulatory organization, whether commenced or
threatened, in respect thereof, "Claims") to which any of them may become
                                 ------
subject insofar as such Claims arise out of or are based upon:  (i) any untrue
statement or alleged untrue statement of a material fact in a Registration
Statement or the omission or alleged omission to state therein a material fact
required to be stated or necessary to make the statements therein not
misleading, (ii) any untrue statement or alleged untrue statement of a material
fact contained in any preliminary prospectus if used prior to the effective date
of such Registration Statement, or contained in the final prospectus (as amended
or supplemented, if the Company files any amendment thereof or supplement
thereto with the SEC) or the omission or alleged omission to state therein any
material fact necessary

                                       11
<PAGE>

to make the statements made therein, in light of the circumstances under which
the statements therein were made, not misleading, or (iii) any violation or
alleged violation by the Company of the Securities Act, the Exchange Act, any
other law, including, without limitation, any state securities law, or any rule
or regulation thereunder relating to the offer or sale of the Registrable
Securities (the matters in the foregoing clauses (i) through (iii) being,
collectively, "Violations"). The Company shall reimburse each such Indemnified
               ----------
Person, promptly as such expenses are incurred and are due and payable, for any
reasonable legal fees or other reasonable expenses incurred by them in
connection with investigating or defending any such Claim. Notwithstanding
anything to the contrary contained herein, the indemnification agreement
contained in this Section 6.1: (x) shall not apply to an Indemnified Person with
respect to a Claim arising out of or based upon a Violation which occurs in
reliance upon and in conformity with information furnished in writing to the
Company by such Indemnified Person expressly for use in the Registration
Statement or any such amendment thereof or supplement thereto; (y) shall not
apply to amounts paid in settlement of any Claim if such settlement is effected
without the prior written consent of the Company, which consent shall not be
unreasonably withheld; and (z) with respect to any preliminary prospectus, shall
not inure to the benefit of any Indemnified Person if the untrue statement or
omission of material fact contained in the preliminary prospectus was corrected
on a timely basis in the prospectus, as then amended or supplemented, if such
corrected prospectus was timely made available by the Company pursuant to
Section 3.3 hereof, and the Indemnified Person was promptly advised in writing
not to use the incorrect prospectus prior to the use giving rise to a Violation
and such Indemnified Person, notwithstanding such advice, used it. Such
indemnity shall remain in full force and effect regardless of any investigation
made by or on behalf of the Indemnified Person and shall survive the transfer of
the Registrable Securities by a Holder pursuant to Article IX.

     6.2  In connection with any Registration Statement in which a Holder is
participating, each such Holder agrees to indemnify, hold harmless and defend,
to the same extent and in the same manner set forth in Section 6.1, the Company,
each of its directors, each of its officers who signs the Registration
Statement, its employees, underwriters, agents and persons, if any, who control
the Company within the meaning of Section 15 of the Securities Act or Section 20
of the Exchange Act, and any other stockholder selling securities pursuant to
the Registration Statement, together with its directors, officers and members,
and any person who controls such stockholder or underwriter within the meaning
of the Securities Act or the Exchange Act (such an "Indemnified Party"), against
                                                    -----------------
any Claim to which any of them may become subject, under the Securities Act, the
Exchange Act or otherwise, insofar as such Claim arises out of or is based upon
any Violation, in each case to the extent (and only to the extent) that such
Violation occurs in reliance upon and in conformity with written information
furnished to the Company by such Holder expressly for use in connection with
such Registration Statement; and such Holder will reimburse any legal or other
expenses (promptly as such expenses are incurred and are due and payable)
reasonably incurred by them in connection with investigating or defending any
such Claim; provided, however, that the indemnity agreement contained in this
Section 6.2 shall not apply to amounts paid in settlement of any Claim if such
settlement is effected without the prior written consent of such Holder, which
consent shall not be unreasonably withheld; provided, further, however, that a
Holder shall be liable under this Agreement (including this Section 6.2 and
Article VII) for only that amount as does not exceed the net proceeds

                                       12
<PAGE>

actually received by such Holder as a result of the sale of Registrable
Securities pursuant to such Registration Statement. Such indemnity shall remain
in full force and effect regardless of any investigation made by or on behalf of
such Indemnified Party and shall survive the transfer of the Registrable
Securities by a Holder pursuant to Article IX. Notwithstanding anything to the
contrary contained herein, the indemnification agreement contained in this
Section 6.2 with respect to any preliminary prospectus shall not inure to the
benefit of any Indemnified Party if the untrue statement or omission of material
fact contained in the preliminary prospectus was corrected on a timely basis in
the prospectus, as then amended or supplemented, and the Indemnified Party
failed to utilize such corrected prospectus.

     6.3  Promptly after receipt by an Indemnified Person or Indemnified Party
under this Article VI of notice of the commencement of any action (including any
governmental action), such Indemnified Person or Indemnified Party shall, if a
Claim in respect thereof is to be made against any indemnifying party under this
Article VI, deliver to the indemnifying party a written notice of the
commencement thereof, and the indemnifying party shall have the right to
participate in, and, to the extent the indemnifying party so desires, jointly
with any other indemnifying party similarly noticed, to assume control of the
defense thereof with counsel mutually satisfactory to the indemnifying party and
the Indemnified Person or the Indemnified Party, as the case may be; provided,
however, that such indemnifying party shall diligently pursue such defense and
that such indemnifying party shall not be entitled to assume such defense and an
Indemnified Person or Indemnified Party shall have the right to retain its own
counsel with the fees and expenses to be paid by the indemnifying party, if the
representation by such counsel of the Indemnified Person or Indemnified Party
and the indemnifying party would be inappropriate due to actual or potential
conflicts of interest between such Indemnified Person or Indemnified Party and
any other party represented by such counsel in such proceeding or the actual or
potential defendants in, or targets of, any such action include both the
Indemnified Person or the Indemnified Party and any such Indemnified Person or
Indemnified Party reasonably determines that there may be legal defenses
available to such Indemnified Person or Indemnified Party which are different
from or in addition to those available to such indemnifying party.  The
indemnifying party shall pay for only one separate legal counsel for the
Indemnified Persons or the Indemnified Parties, as applicable, and such legal
counsel shall be selected by Holder holding a majority-in-interest of the
Registrable Securities included in the Registration Statement to which the Claim
relates (with the approval of each Holder which holds Registrable Securities
included in such Registration Statement),  if the Holder is entitled to
indemnification hereunder, or by the Company, if the Company is entitled to
indemnification hereunder, as applicable.  The failure to deliver written notice
to the indemnifying party within a reasonable time of the commencement of any
such action shall not relieve such indemnifying party of any liability to the
Indemnified Person or Indemnified Party under this Article VI, except to the
extent that the indemnifying party is actually prejudiced in its ability to
defend such action.  The indemnification required by this Article VI shall be
made by periodic payments of the amount thereof during the course of the
investigation or defense, as such expense, loss, damage or liability is incurred
and is due and payable.

                                       13
<PAGE>

                                  ARTICLE VII
                                 CONTRIBUTION
                                 ------------

     To the extent any indemnification by an indemnifying party is prohibited or
limited by law, the indemnifying party agrees to make the maximum contribution
with respect to any amounts for which it would otherwise be liable under Article
VI to the fullest extent permitted by law; provided, however, that (i) no person
guilty of fraudulent misrepresentation (within the meaning of Section 11(f) of
the Securities Act) shall be entitled to contribution from any person of
Registrable Securities who was not guilty of such fraudulent misrepresentation,
and (ii) contribution (together with any indemnification or other obligations
under this Agreement) by any seller of Registrable Securities shall be limited
in amount to the net amount of proceeds received by such seller from the sale of
such Registrable Securities.

                                 ARTICLE VIII
                        REPORTS UNDER THE EXCHANGE ACT
                        ------------------------------

     With a view to making available to the Holders the benefits of Rule 144
promulgated under the Securities Act or any other similar rule or regulation of
the SEC that may at any time permit the Holders to sell securities of the
Company to the public without registration ("Rule 144"), the Company agrees to:
                                             --------

     8.1  File with the SEC in a timely manner and make and keep available all
reports and other documents required of the Company under the Securities Act and
the Exchange Act so long as the Company remains subject to such requirements (it
being understood that nothing herein shall limit the Company's obligations under
Section 4.3 of the Securities Purchase Agreement) and the filing and
availability of such reports and other documents is required for the applicable
provisions of Rule 144; and

     8.2  Furnish to each Holder so long as such Holder holds Preferred Stock,
the Common Stock Warrant or Registrable Securities, promptly upon request, (i) a
written statement by the Company that it has complied with the reporting
requirements of Rule 144, the Securities Act and the Exchange Act, (ii) a copy
of the most recent annual or quarterly report of the Company and such other
reports and documents so filed by the Company, and (iii) such other information
as may be reasonably requested to permit the Holder to sell such securities
pursuant to Rule 144 without registration.

                                  ARTICLE IX
                       ASSIGNMENT OF REGISTRATION RIGHTS
                       ---------------------------------

     The rights of the Holders hereunder, including the right to have the
Company register Registrable Securities pursuant to this Agreement, shall be
automatically assigned by such Holder to any transferee of all or any portion of
the Preferred Stock, the Common Stock Warrant or the

                                       14
<PAGE>

Registrable Securities if: (a) the Holders agrees in writing with the transferee
or assignee to assign such rights, and a copy of such agreement is furnished to
the Company within a reasonable time after such assignment, (b) the Company is,
within a reasonable time after such transfer or assignment, furnished with
written notice of (i) the name and address of such transferee or assignee, and
(ii) the securities with respect to which such registration rights are being
transferred or assigned, (c) following such transfer or assignment, the further
disposition of such securities by the transferee or assignee is restricted under
the Securities Act or applicable state securities laws, and (d) at or before the
time the Company receives the written notice contemplated by clause (ii) of this
sentence, the transferee or assignee agrees in writing for the benefit of the
Company to be bound by all of the provisions contained herein. The rights of a
Holder hereunder with respect to any Registrable Securities not transferred (and
not represented by Preferred Stock or the Warrant transferred) shall not be
assigned by virtue of the transfer of other Registrable Securities or
transferred Preferred Stock or the Common Stock Warrant representing other
Registrable Securities. Any such transferee who succeeds to rights hereunder
shall be deemed to have a separate agreement with the Company independent of
this Agreement.

                                   ARTICLE X
                       AMENDMENT OF REGISTRATION RIGHTS
                       --------------------------------

     Provisions of this Agreement may be amended and the observance thereof may
be waived (either generally or in a particular instance and either retroactively
or prospectively), only with written consent of the Company and the Holders of a
majority of the outstanding Registrable Securities.  In the event of the
assignment of rights hereunder pursuant to Article IX, the Company shall not
take any action pursuant to such assignment rights that would adversely affect a
Holder's rights hereunder without such Holders' consent.

                                  ARTICLE XI
                                 MISCELLANEOUS
                                 -------------

     11.1  A person or entity is deemed to be a holder (or a holder in interest)
of Registrable Securities whenever such person or entity owns of record such
Registrable Securities (or the Preferred Stock or the Common Stock Warrant which
may be converted into or exercised for Registrable Securities).  If the Company
receives conflicting instructions, notices or elections from two or more persons
or entities with respect to the same Registrable Securities, the Company shall
act upon the basis of instructions, notice or election received from the
registered owner of such Registrable Securities (or Preferred Stock or the
Common Stock Warrant, as the case may be).

     11.2  Any notices herein required or permitted to be given shall be in
writing and may be personally served or delivered by courier or by machine-
generated confirmed telecopy, and shall be deemed delivered at the time and date
of receipt (which shall include telephone line facsimile transmission).  The
addresses for such communications shall be:

                                       15
<PAGE>

          If to the Company:

               Voxware, Inc.
               Lawrenceville Office Park
               P.O. Box 5363
               Princeton, New Jersey 08543
               or
               168 Franklin Corner Road
               Suite 3
               Lawrenceville, NJ 08648

               Telephone: (609) 514-4100
               Telecopy: (609) 514-4101
               Attention: Nicholas Narlis

               with a copy to:

               Fulbright & Jaworski L.L.P.
               666 Fifth Avenue
               New York, New York 10103

               Telecopy: (212) 318-3400
               Attention: Paul Jacobs, Esq.

If to any Holder, at such address as such Holder, shall have provided in writing
to the Company, or at such other address as each such party furnishes by notice
given in accordance with this Section 11.2.

     11.3  Failure of any party to exercise any right or remedy under this
Agreement or otherwise, or delay by a party in exercising such right or remedy,
shall not operate as a waiver thereof.

     11.4  This Agreement shall be governed by and construed in accordance with
the laws of the State of New York applicable to contracts made and to be
performed in the State of New York without regard to conflict of laws principles
thereof.  The Company irrevocably consents to the jurisdiction of the federal
courts located in the State of New York and the state courts of the State of New
York located in the County of New York in the State of New York in any suit or
proceeding based on or arising under this Agreement and irrevocably agrees that
all claims in respect of such suit or proceeding may be determined in such
courts.  The Company irrevocably waives the defense of an inconvenient forum to
the maintenance of such suit or proceeding.  The parties hereto further agree
that service of process upon the parties hereto mailed by first class mail shall
be deemed in every respect effective service of process upon each such party in
any such suit or proceeding.

                                       16
<PAGE>

Nothing herein shall affect either party's right to serve process in any other
manner permitted by law. The parties hereto agree that a final non-appealable
judgment in any such suit or proceeding shall be conclusive and may be enforced
in other jurisdictions by suit on such judgment or in any other lawful manner.

     11.5  This Agreement, the Preferred Stock, the Warrant and the Securities
Purchase Agreement (including all schedules and exhibits thereto and all
certificates and opinions required thereby) constitute the entire agreement
among the parties hereto with respect to the subject matter hereof and thereof.
There are no restrictions, promises, warranties or undertakings, other than
those set forth or referred to herein and therein.  This Agreement, the
Preferred Stock, the Common Stock Warrant and the Securities Purchase Agreement
supersede all prior agreements and understandings among the parties hereto with
respect to the subject matter hereof and thereof.

     11.6  Subject to the requirements of Article IX hereof, this Agreement
shall inure to the benefit of and be binding upon the successors and assigns of
each of the parties hereto.  Notwithstanding anything to the contrary contained
herein, including, without limitation, Article IX, the rights of a Holder
hereunder shall be assignable to and exercisable by a bona fide pledgee of the
Registrable Securities in connection with a Holder's margin or brokerage
accounts.

     11.7  The headings in this Agreement are for convenience of reference only
and shall not limit or otherwise affect the meaning hereof.

     11.8  This Agreement may be executed in two or more counterparts, each of
which shall be deemed an original but all of which shall constitute one and the
same agreement.  This Agreement, once executed by a party, may be delivered to
the other party hereto, by facsimile transmission of a copy of this Agreement
bearing the signature of the party so delivering this Agreement.

     11.9  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.

     11.10 In the event Holder shall sell or otherwise transfer any of such
Holder's Registrable Securities, each transferee shall be allocated a pro rata
portion of the number of Registrable Securities included on a Registration
Statement for such transferor.  Any shares of Common Stock included on a
Registration Statement and which remain allocated to any person or entity which
does not hold any Registrable Securities shall be allocated to the remaining
participant, in such Registration Statement, pro rata based on the number of
shares of Registrable Securities then held by such participant.  Without
implication that the contrary would otherwise be true, for purposes of this
paragraph, all Preferred Stock and the Warrant then outstanding shall be assumed
converted into and exercised for Registrable Securities (without giving effect
to any limitations on conversion or exercise).

                                       17
<PAGE>

     11.11  If any provision of this Agreement shall be invalid or
unenforceable, such invalidity or unenforceability shall not affect the validity
or enforceability of the remainder of this Agreement.

     11.12  In the event any actions or approvals hereunder are required to be
taken by the Holders, except as otherwise specifically provided herein, such
actions may be taken or approvals given or refused to be given by a majority of
the Holders of the then outstanding Registrable Securities.

                                     * * *

                                       18
<PAGE>

     IN WITNESS WHEREOF, the parties have caused this Agreement to be duly
executed as of the date first above written.

                                    COMPANY:

                                    VOXWARE, INC.

                                    By: /s/ Bathsheba J. Malsheen
                                        -------------------------
                                    Name:  Bathsheba J. Malsheen
                                    Title: President and Chief Executive
                                           Officer

                                       19
<PAGE>

Holder:

CASTLE CREEK TECHNOLOGY PARTNERS LLC

By:  Castle Creek Partners, L.L.C.
Its: Investment Manager

By:  /s/ Michael L. Spolan
     ---------------------
Name:    Michael L. Spolan
Title:   Managing Director

     Address:  77 W. Wacker Drive, Suite 4040
               Chicago, Illinois 60601
               Facsimile: (312)499-6999
Copy to:
               Wolfe, Block, Schorr and Solis-Cohen LLP
               1650 Arch Street
               Philadelphia, PA 19103-2097

               Attn: Jason M. Shargel, Esq.
               Telephone No.: (215) 977-2216
               Facsimile: (215) 977-2334

JURISDICTION: Delaware limited liability company

AGGREGATE NUMBER OF SHARES OF SERIES A PREFERRED STOCK PURCHASED AT CLOSING:
4,000 shares
----------------

AGGREGATE NUMBER OF WARRANT SHARES REPRESENTED BY COMMON STOCK WARRANT

________________

PURCHASE PRICE: $  4,000,000
                -------------------

                                       20
<PAGE>

EXHIBIT 1
to Registration Rights Agreement
                                     [Date]
[Name and address
of transfer agent]

               RE: VOXWARE, INC.

Ladies and Gentlemen:

     We are counsel to Voxware, Inc., a Delaware corporation (the "Company"),
                                                                   -------
and we understand that [Name of Holder] (the "Holder") has purchased from the
                                              ------
Company an amount of the Company's Series A Preferred Stock (the "Preferred
                                                                  ---------
Stock") convertible into shares of the Company's common stock, $0.01 per share
-----
(the "Common Stock"), and warrants to purchase shares of the Common Stock of the
      ------------
Company's Common Stock (the "Common Stock Warrant").  The Preferred Stock and
                             --------------------
the Common Stock Warrants were purchased by the Holders pursuant to a Securities
Purchase Agreement, dated as of August 10, 2000, by and among the Company and
the signatories thereto (the "Agreement").  Pursuant to a Registration Rights
                              ---------
Agreement, dated as of August 15, 2000, by and among the Company and the
signatories thereto (the "Registration Rights Agreement"), the Company agreed
                          -----------------------------
with the Holders, among other things, to register the Registrable Securities (as
that term is defined in the Registration Rights Agreement) under the Securities
Act of 1933, as amended (the "Securities Act"), upon the terms provided in the
                              --------------
Registration Rights Agreement.  In connection with the Company's obligations
under the Registration Rights Agreement, on August, __, 2000, the Company filed
a Registration Statement on Form S-3 (File No. 333- __________) (the
"Registration Statement") with the Securities and Exchange Commission (the
 ----------------------
"SEC") relating to the Registrable Securities, which names the Holders as a
 ---
selling stockholder thereunder.

[Other customary introductory and scope of examination language to be inserted]

     Based on the foregoing, we are of the opinion that the Registrable
Securities have been registered under the Securities Act.

  [Other appropriate customary language reasonably acceptable to holder to be
                                  included.]

                                    Very truly yours,

cc: [Name of Holder]

                                       21

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