UPLAND SOFTWARE, INC.
2010 STOCK PLAN
RESTRICTED STOCK PURCHASE AGREEMENT
Unless otherwise defined herein, the terms defined in the 2010 Stock Plan, as
amended (the “Plan”) shall have the same defined meanings in this Restricted
Stock Purchase Agreement (the “Agreement”).
I.NOTICE OF GRANT OF RESTRICTED STOCK
Name:
Timothy Mattox

Address:
8001 Big View Dr.

Austin, Texas 78730
The undersigned Participant has been granted a right to purchase Common Stock of
the Company, subject to the terms and conditions of the Plan and this Agreement,
as follows:
Date of Grant:    September 2, 2014    
Vesting Commencement Date:    July 14, 2014    
Purchase Price per Share:    $1.43    
Total Number of Shares Granted:    500,000    
Total Purchase Price:    $715,000    
Vesting Schedule:
▪
Ten percent (10%) of the Shares subject to this Agreement shall be released from
the Company’s Repurchase Option on the one (1) year anniversary of the Vesting
Commencement Date, then

▪
Twenty percent (20%) of the Shares subject to this Agreement shall be released
from the Company’s Repurchase Option in twelve (12) equal installments on the
corresponding day of each month (or if there is no corresponding day in any such
month, on the last day of such month) over the period from the first anniversary
of the Vesting Commencement Date to the second anniversary of the Vesting
Commencement Date, then

•
Thirty percent (30%) of the Shares subject to this Agreement shall be released
from the Company’s Repurchase Option in twelve (12) equal installments on the
corresponding day of each month (or if there is no corresponding day in any such
month, on the last

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day of such month) over the period from the second anniversary of the Vesting
Commencement Date to the third anniversary of the Vesting Commencement Date,
then
•
Forty percent (40%) of the Shares subject to this Agreement shall be released
from the Company’s Repurchase Option in twelve (12) equal installments on the
corresponding day of each month (or if there is no corresponding day in any such
month, on the last day of such month) over the period from the third anniversary
of the Vesting Commencement Date to the fourth anniversary of the Vesting
Commencement Date, and

All of the vesting, as described above, is subject to the Participant continuing
to be a Service Provider through each such date.
In addition, notwithstanding the foregoing Vesting Schedule, in the event of a
Change in Control (as defined in the Plan), the release of the Shares from the
Company’s Repurchase Option Shares shall accelerate as to that number of Shares
that would have been released from the Company’s Repurchase Option had
Participant remained an employee for two (2) additional years, in accordance
with the Vesting Schedule above.
Any of the Shares which have not yet been released from the Company’s Repurchase
Option are referred to herein as “Unreleased Shares.” The Shares which have been
released from the Company’s Repurchase Option shall be delivered to Participant
at Participant’s request (see Section 11 of Part II of this Agreement).
Notwithstanding the foregoing, in the event that Participant is terminated
without Cause or leaves for Good Reason within twelve months following a Change
in Control (as defined in the Plan), then one hundred percent (100%) of the
shares subject to the Repurchase Option shall accelerate as of immediately prior
to such termination. For the purposes of this Agreement, “Cause” means (i)
Participant’s willful or grossly negligent failure to substantially perform the
duties and obligations of Participant’s position with the Company; (ii) any act
of personal dishonesty, fraud or misrepresentation taken by Participant which
was intended to result in substantial gain or personal enrichment of Participant
at the expense of the Company; (iii) Participant’s violation of a federal or
state law or regulation applicable to the Company’s business which violation was
or is reasonably likely to be injurious to the Company; (iv) Participant’s
conviction of, or plea of nolo contendere or guilty to, a felony under the laws
of the United States or any State, excluding felonies for minor traffic
violation and vicarious liability (so long as Participant did not know of the
felony and did not willfully violate the law); (v) Participant’s material breach
of the terms of the Proprietary Information Agreement with the Company. For the
purposes of this Agreement, “Good Reason” means (i) without Participant’s
consent, a material reduction of Participant’s duties or responsibilities
relative to Participant’s duties or responsibilities as in effect immediately
prior to such reduction; provided, however, any reduction in Participant’s
duties or responsibilities resulting solely from the Company being acquired by
and made a part of a larger entity (as, for example, when a chief executive
officer becomes an employee of the acquiring corporation following a Change in
Control but is not the chief executive officer of the acquiring corporation)
shall not constitute Good Reason; (ii) without Participant’s written consent, a
material reduction in Participant’s base salary as in effect immediately prior
to such reduction, unless such reduction is part of a reduction in expenses
generally affecting senior executives of the Company; (iii) without

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Participant’s consent, a material reduction by the Company in the kind or level
of employee benefits to which Participant was entitled immediately prior to such
reduction, with the result that Participant’s overall benefits package is
materially reduced, unless such reduction is part of a reduction in benefits
generally affecting senior executives of the Company; or (iv) without
Participant’s consent, a relocation to a facility or a location more than fifty
(50) miles from Participant’s then current present working locations. Good
Reason shall not exist unless Participant provides (i) notice to the Company
within ninety (90) days of the initial existence of the condition triggering
Good Reason and (ii) the Company the opportunity of at least thirty (30) days to
cure such condition. A termination from service shall not be considered for Good
Reason if such termination occurs later than two (2) years following the initial
existence of the Good Reason condition. Notwithstanding the foregoing, if
Participant terminates employment with the Company for Good Reason, but the
Company discovers after such termination that Participant’s conduct during the
employment term would have entitled the Company to terminate Participant for
Cause, then Participant’s termination shall be for Cause and not for Good Reason
and Participant shall remit all amounts paid to Participant for termination for
Good Reason.
II.    AGREEMENT
1.    Sale of Stock. The Administrator of the Company hereby agrees to sell to
the Participant named in the Notice of Grant of Restricted Stock in Part I of
this Agreement (“Participant”), and Participant hereby agrees to purchase the
number of Shares set forth in the Notice of Grant of Restricted Stock, at the
Purchase Price per Share set forth in the Notice of Grant of Restricted Stock
(the “Purchase Price”), and subject to the terms and conditions of the Plan,
which is incorporated herein by reference. Subject to Section 19 of the Plan, in
the event of a conflict between the terms and conditions of the Plan and this
Agreement, the terms and conditions of the Plan shall prevail.
2.    Payment of Purchase Price. The Company hereby acknowledges that the
purchase price for the Shares has been paid by Participant via services
previously rendered to the Company, such services having a value at least equal
to the Purchase Price.
3.    Participant’s Representations. In the event the Shares have not been
registered under the Securities Act of 1933, as amended, at the time this
Restricted Stock Award is exercised, Participant shall, if required by the
Company, concurrently with the exercise of all or any portion of this Restricted
Stock Award, deliver to the Company his or her Investment Representation
Statement in the form attached hereto as Exhibit A.
4.    Lock-Up Period. Participant hereby agrees that Participant shall not
offer, pledge, sell, contract to sell, sell any option or contract to purchase,
purchase any option or contract to sell, grant any option, right or warrant to
purchase, lend, or otherwise transfer or dispose of, directly or indirectly, any
Common Stock (or other securities) of the Company or enter into any swap,
hedging or other arrangement that transfers to another, in whole or in part, any
of the economic consequences of ownership of any Common Stock (or other
securities) of the Company held by Participant (other than those included in the
registration) for a period specified by the representative of the underwriters
of Common Stock (or other securities) of the Company not to exceed one hundred
and eighty (180) days following the effective date of any registration statement
of the Company filed under the Securities Act (or such other period as may be
requested by the Company or the underwriters to accommodate regulatory
restrictions on (i) the publication or other distribution of research reports
and (ii) analyst recommendations and

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opinions, including, but not limited to, the restrictions contained in NASD
Rule 2711(f)(4) or NYSE Rule 472(f)(4), or any successor provisions or
amendments thereto).
Participant agrees to execute and deliver such other agreements as may be
reasonably requested by the Company or the underwriter which are consistent with
the foregoing or which are necessary to give further effect thereto. In
addition, if requested by the Company or the representative of the underwriters
of Common Stock (or other securities) of the Company, Participant shall provide,
within ten (10) days of such request, such information as may be required by the
Company or such representative in connection with the completion of any public
offering of the Company’s securities pursuant to a registration statement filed
under the Securities Act. The obligations described in this Section 4 shall not
apply to a registration relating solely to employee benefit plans on Form S-1 or
Form S-8 or similar forms that may be promulgated in the future, or a
registration relating solely to a Commission Rule 145 transaction on Form S-4 or
similar forms that may be promulgated in the future. The Company may impose
stop-transfer instructions with respect to the shares of Common Stock (or other
securities) subject to the foregoing restriction until the end of said one
hundred and eighty (180) day (or other) period. Participant agrees that any
transferee of the Restricted Stock Award or shares acquired pursuant to the
Restricted Stock Award shall be bound by this Section 4.
5.    Non-Transferability of Restricted Stock. This Restricted Stock Award may
not be transferred in any manner otherwise than by will or by the laws of
descent or distribution and may be exercised during the lifetime of Participant
only by Participant. The terms of the Plan and this Agreement shall be binding
upon the executors, administrators, heirs, successors and assigns of
Participant.
6.    Tax Consequences. Participant has reviewed with Participant’s own tax
advisors the federal, state, local and foreign tax consequences of this
investment and the transactions contemplated by this Agreement. Participant is
relying solely on such advisors and not on any statements or representations of
the Company or any of its agents. Participant understands that Participant (and
not the Company) shall be responsible for Participant’s own tax liability that
may arise as a result of the transactions contemplated by this Agreement.
Participant understands that Section 83 of the Internal Revenue Code of 1986, as
amended (the “Code”), taxes as ordinary income the difference between the
purchase price for the Shares and the Fair Market Value of the Shares as of the
date any restrictions on the Shares lapse. In this context, “restriction”
includes the right of the Company to buy back the Shares pursuant to the
Repurchase Option. Participant understands that Participant may elect to be
taxed at the time the Shares are purchased rather than when and as the
Repurchase Option expires by filing an election under Section 83(b) of the Code
with the IRS within thirty (30) days from the date of purchase. The form for
making this election is attached as Exhibit B-4 hereto.
THE PARTICIPANT ACKNOWLEDGES THAT IT IS THE PARTICIPANT’S SOLE RESPONSIBILITY
AND NOT THE COMPANY’S TO FILE TIMELY THE ELECTION UNDER SECTION 83(b), EVEN IF
THE PARTICIPANT REQUESTS THE COMPANY OR ITS REPRESENTATIVES TO MAKE THIS FILING
ON THE PARTICIPANT’S BEHALF.
7.    Tax Withholding. Pursuant to such procedures as the Administrator may
specify from time to time, the Company shall withhold the minimum amount
required to be withheld for the payment of income, employment and other taxes
which the Company determines must be withheld (the “Withholding Taxes”) with
respect to Shares released from the Company’s Repurchase Option by, in

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the Administrator’s discretion: (i) withholding otherwise deliverable Shares
upon release from the Company’s Repurchase Option having a Fair Market Value
equal the amount of such Withholding Taxes, (ii) withholding the amount of such
Withholding Taxes from Participant’s paycheck(s), (iii) requiring Participant to
make appropriate arrangements with the Company (or the Parent or Subsidiary
employing or retaining Participant) for the satisfaction of all Withholding
Taxes, or (iv) a combination of the foregoing. The Company shall not retain
fractional Shares to satisfy any portion of the Withholding Taxes. Accordingly,
if any withholding is done through the withholding of Shares, Participant shall
pay to the Company an amount in cash sufficient to satisfy the remaining
Withholding Taxes due and payable as a result of the Company not retaining
fractional Shares. Should the Company be unable to procure such cash amounts
from Participant, Participant agrees and acknowledges that Participant is giving
the Company permission to withhold from Participant’s paycheck(s) an amount
equal to the remaining Withholding Taxes due and payable as a result of the
Company not retaining fractional Shares. Participant acknowledges and agrees
that the Company may refuse to honor the exercise and refuse to deliver the
Shares if such withholding amounts are not delivered at the time of purchase.
8.    No Guarantee of Continued Service. PARTICIPANT ACKNOWLEDGES AND AGREES
THAT THE RELEASE OF SHARES FROM THE REPURCHASE OPTION OF THE COMPANY PURSUANT TO
THE VESTING SCHEDULE HEREOF IS EARNED ONLY BY CONTINUING AS A SERVICE PROVIDER
AT THE WILL OF THE COMPANY (OR THE PARENT OR SUBSIDIARY EMPLOYING OR RETAINING
PARTICIPANT) AND NOT THROUGH THE ACT OF BEING HIRED OR PURCHASING SHARES
HEREUNDER. PARTICIPANT FURTHER ACKNOWLEDGES AND AGREES THAT THIS AGREEMENT, THE
TRANSACTIONS CONTEMPLATED HEREUNDER AND THE VESTING SCHEDULE SET FORTH HEREIN DO
NOT CONSTITUTE AN EXPRESS OR IMPLIED PROMISE OF CONTINUED ENGAGEMENT AS A
SERVICE PROVIDER FOR THE VESTING PERIOD, FOR ANY PERIOD, OR AT ALL, AND SHALL
NOT INTERFERE IN ANY WAY WITH PARTICIPANT’S RIGHT OR THE RIGHT OF THE COMPANY
(OR THE PARENT OR SUBSIDIARY EMPLOYING OR RETAINING PARTICIPANT) TO TERMINATE
PARTICIPANT’S RELATIONSHIP AS A SERVICE PROVIDER AT ANY TIME, WITH OR WITHOUT
CAUSE.
9.    Repurchase Option.
(a)    In the event Participant’s continuous status as a Service Provider
terminates for any or no reason (including death or Disability), the Company
shall, upon the date of such termination (as reasonably fixed and determined by
the Company), have an irrevocable, exclusive option for a period of ninety (90)
days from such date to repurchase up to that number of Shares which constitute
the Unreleased Shares (as defined in Part I of this Agreement) at the Purchase
Price per share (the “Repurchase Price”) (the “Repurchase Option”).
(b)    The Repurchase Option shall be exercised by the Company by delivering
written notice to Participant or Participant’s executor (with a copy to the
Escrow Holder (as defined in Section 11)) AND, at the Company’s option, (i) by
delivering to Participant or Participant’s executor a check in the amount of the
aggregate Repurchase Price, or (ii) by the Company canceling an amount of
Participant’s indebtedness to the Company equal to the aggregate Repurchase
Price, or (iii) by a combination of (i) and (ii) so that the combined payment
and cancellation of indebtedness equals such aggregate

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Repurchase Price. Upon delivery of such notice and the payment of the aggregate
Repurchase Price in any of the ways described above, the Company shall become
the legal and beneficial owner of the Unreleased Shares being repurchased and
all rights and interests therein or relating thereto, and the Company shall have
the right to retain and transfer to its own name the number of Unreleased Shares
being repurchased by the Company.
(c)    Whenever the Company shall have the right to repurchase the Unreleased
Shares hereunder, the Company may designate and assign one or more employees,
officers, directors or shareholders of the Company or other persons or
organizations to exercise all or a part of the Company’s Repurchase Option to
purchase all or a part of the Unreleased Shares. If the Fair Market Value of the
Unreleased Shares to be repurchased on the date of such designation or
assignment (the “Repurchase FMV”) exceeds the aggregate Repurchase Price of the
Unreleased Shares, then each such designee or assignee shall pay the Company
cash equal to the difference between the Repurchase FMV and the aggregate
Repurchase Price of Unreleased Shares to be purchased.
(d)    If the Company or its assignee does not elect to exercise the Repurchase
Option conferred above by giving the requisite notice within ninety (90) days
following Participant’s termination as a Service Provider, the Repurchase Option
shall terminate.
10.    Restriction on Transfer. Except for the escrow described in Section 11 or
transfer of the Shares to the Company or its assignees contemplated by this
Agreement, none of the Shares or any beneficial interest therein shall be
transferred, encumbered or otherwise disposed of in any way until the release of
such Shares from the Company’s Repurchase Option in accordance with the
provisions of this Agreement, other than by will or the laws of descent and
distribution. Any distribution or delivery to be made to Participant under this
Agreement shall, if Participant is then deceased, be made to Participant’s
designated beneficiary, or if no beneficiary survives Participant, to the
administrator or executor of Participant’s estate. Any such transferee must
furnish the Company with (a) written notice of his or her status as transferee,
and (b) evidence satisfactory to the Company to establish the validity of the
transfer and compliance with any laws or regulations pertaining to said
transfer.
11.    Escrow of Shares.
(a)    To ensure the availability for delivery of Participant’s Unreleased
Shares upon exercise of the Repurchase Option by the Company, Participant will,
upon execution of this Agreement, deliver and deposit with an escrow holder
designated by the Company (the “Escrow Holder”) the share certificates
representing the Unreleased Shares, together with the Assignment Separate from
Certificate (the “Stock Assignment”) duly endorsed in blank, attached hereto as
Exhibit B-1. The Unreleased Shares and Stock Assignment shall be held by the
Escrow Holder, pursuant to the Joint Escrow Instructions of the Company and
Participant attached as Exhibit B-2 hereto, until such time as the Company’s
Repurchase Option expires.
(b)    The Escrow Holder shall not be liable for any act it may do or omit to do
with respect to holding the Unreleased Shares in escrow and while acting in good
faith and in the exercise of its judgment.

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(c)    If the Company or any assignee exercises its Repurchase Option hereunder,
the Escrow Holder, upon receipt of written notice of such option exercise from
the proposed transferee, shall take all steps necessary to accomplish such
transfer. Participant hereby appoints the Escrow Holder with full power of
substitution, as Participant’s true and lawful attorney‑in‑fact with irrevocable
power and authority in the name and on behalf of Participant to take any action
and execute all documents and instruments, including, without limitation, stock
powers which may be necessary to transfer the certificate or certificates
evidencing such Unreleased Shares to the Company upon such termination.
(d)    When the Repurchase Option has been exercised or expires unexercised or a
portion of the Shares has been released from such Repurchase Option, upon
Participant’s request the Escrow Holder shall promptly cause a new certificate
to be issued for such released Shares and shall deliver such certificate to the
Company or Participant, as the case may be.
(e)    Subject to the terms hereof, Participant shall have all the rights of a
shareholder with respect to such Shares while they are held in escrow, including
without limitation, the right to vote the Shares and receive any cash dividends
declared thereon.
(f)    In the event of any merger, reorganization, consolidation,
recapitalization, separation, liquidation, stock dividend, split-up, share
combination, or other change in the corporate structure of the Company affecting
the Common Stock, the Shares shall be increased, reduced or otherwise changed,
and by virtue of any such change Participant shall in his or her capacity as
owner of Unreleased Shares that have been awarded to him or her be entitled to
new or additional or different shares of stock, cash or securities (other than
rights or warrants to purchase securities); such new or additional or different
shares, cash or securities shall thereupon be considered to be “Unreleased
Shares” and shall be subject to all of the conditions and restrictions which
were applicable to the Unreleased Shares pursuant to this Agreement. If
Participant receives rights or warrants with respect to any Unreleased Shares,
such rights or warrants may be held or exercised by Participant, provided that
until such exercise any such rights or warrants and after such exercise any
shares or other securities acquired by the exercise of such rights or warrants
shall be considered to be Unreleased Shares and shall be subject to all of the
conditions and restrictions which were applicable to the Unreleased Shares
pursuant to this Agreement. The Administrator in its absolute discretion at any
time may accelerate the vesting of all or any portion of such new or additional
shares of stock, cash or securities, rights or warrants to purchase securities
or shares or other securities acquired by the exercise of such rights or
warrants.
12.    Company’s Right of First Refusal. Subject to Section 10, before any
Shares held by Participant or any transferee (either being sometimes referred to
herein as the “Holder”) may be sold or otherwise transferred (including transfer
by gift or operation of law), the Company or its assignee(s) shall have a right
of first refusal to purchase the Shares on the terms and conditions set forth in
this Section 12 (the “Right of First Refusal”).
(a)    Notice of Proposed Transfer. The Holder of the Shares shall deliver to
the Company a written notice (the “Notice”) stating: (i) the Holder’s bona fide
intention to sell or otherwise transfer such Shares; (ii) the name of each
proposed purchaser or other transferee (“Proposed Transferee”); (iii) the number
of Shares to be transferred to each Proposed Transferee; and (iv) the bona fide
cash price or other consideration for which the Holder proposes to transfer the
Shares (the “Offered Price”), and the Holder shall offer the Shares at the
Offered Price to the Company or its assignee(s).

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(b)    Exercise of Right of First Refusal. At any time within thirty (30) days
after receipt of the Notice, the Company and/or its assignee(s) may, by giving
written notice to the Holder, elect to purchase all, but not less than all, of
the Shares proposed to be transferred to any one or more of the Proposed
Transferees, at the purchase price determined in accordance with subsection (c)
below.
(c)    Purchase Price. The purchase price (“Right of First Refusal Price”) for
the Shares purchased by the Company or its assignee(s) under this Section 12
shall be the Offered Price. If the Offered Price includes consideration other
than cash, the cash equivalent value of the non-cash consideration shall be
determined by the Board in good faith.
(d)    Payment. Payment of the Right of First Refusal Price shall be made, at
the option of the Company or its assignee(s), in cash (by check), by
cancellation of all or a portion of any outstanding indebtedness of the Holder
to the Company (or, in the case of repurchase by an assignee, to the assignee),
or by any combination thereof within thirty (30) days after receipt of the
Notice or in the manner and at the times set forth in the Notice.
(e)    Holder’s Right to Transfer. If all of the Shares proposed in the Notice
to be transferred to a given Proposed Transferee are not purchased by the
Company and/or its assignee(s) as provided in this Section 12, then the Holder
may sell or otherwise transfer such Shares to that Proposed Transferee at the
Offered Price or at a higher price, provided that such sale or other transfer is
consummated within one hundred and twenty (120) days after the date of the
Notice, that any such sale or other transfer is effected in accordance with any
applicable securities laws and that the Proposed Transferee agrees in writing
that the provisions of this Section 12 shall continue to apply to the Shares in
the hands of such Proposed Transferee. If the Shares described in the Notice are
not transferred to the Proposed Transferee within such period, a new Notice
shall be given to the Company, and the Company and/or its assignees shall again
be offered the Right of First Refusal before any Shares held by the Holder may
be sold or otherwise transferred.
(f)    Exception for Certain Family Transfers. Anything to the contrary
contained in this Section 12 notwithstanding, the transfer of any or all of the
Shares during Participant’s lifetime or on Participant’s death by will or
intestacy to Participant’s immediate family or a trust for the benefit of
Participant’s immediate family shall be exempt from the provisions of this
Section 12. “Immediate Family” as used herein shall mean spouse, lineal
descendant or antecedent, father, mother, brother or sister. In such case, the
transferee or other recipient shall receive and hold the Shares so transferred
subject to the provisions of this Agreement, including but not limited to this
Section 12 and Section 9, and there shall be no further transfer of such Shares
except in accordance with the terms of this Section 12.
(g)    Termination of Right of First Refusal. The Right of First Refusal shall
terminate as to any Shares upon the earlier of (i) the first sale of Common
Stock of the Company to the general public, or (ii) a Change in Control in which
the successor corporation has equity securities that are publicly traded.

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13.    Restrictive Legends and Stop-Transfer Orders.
(a)    Legends. Participant understands and agrees that the Company shall cause
the legends set forth below or legends substantially equivalent thereto, to be
placed upon any certificate(s) evidencing ownership of the Shares together with
any other legends that may be required by the Company or by state or federal
securities laws:
THE SECURITIES REPRESENTED HEREBY HAVE NOT BEEN REGISTERED UNDER THE SECURITIES
ACT OF 1933 (THE “ACT”) AND MAY NOT BE OFFERED, SOLD OR OTHERWISE TRANSFERRED,
PLEDGED OR HYPOTHECATED UNLESS AND UNTIL REGISTERED UNDER THE ACT OR, IN THE
OPINION OF COUNSEL SATISFACTORY TO THE ISSUER OF THESE SECURITIES, SUCH OFFER,
SALE OR TRANSFER, PLEDGE OR HYPOTHECATION IS IN COMPLIANCE THEREWITH.
THE SHARES REPRESENTED BY THIS CERTIFICATE ARE SUBJECT TO CERTAIN RESTRICTIONS
ON TRANSFER, A RIGHT OF FIRST REFUSAL, AND A REPURCHASE OPTION HELD BY THE
ISSUER OR ITS ASSIGNEE(S) AS SET FORTH IN THE RESTRICTED STOCK PURCHASE
AGREEMENT BETWEEN THE ISSUER AND THE ORIGINAL HOLDER OF THESE SHARES, A COPY OF
WHICH MAY BE OBTAINED AT THE PRINCIPAL OFFICE OF THE ISSUER. SUCH TRANSFER
RESTRICTIONS, RIGHT OF FIRST REFUSAL AND REPURCHASE OPTION ARE BINDING ON
TRANSFEREES OF THESE SHARES.
THE SHARES REPRESENTED BY THIS CERTIFICATE ARE SUBJECT TO RESTRICTIONS ON
TRANSFER FOR A PERIOD OF TIME FOLLOWING THE EFFECTIVE DATE OF THE UNDERWRITTEN
PUBLIC OFFERING OF THE COMPANY’S SECURITIES SET FORTH IN AN AGREEMENT BETWEEN
THE ISSUER AND THE ORIGINAL HOLDER OF THESE SHARES AND MAY NOT BE SOLD OR
OTHERWISE DISPOSED OF BY THE HOLDER PRIOR TO THE EXPIRATION OF SUCH PERIOD
WITHOUT THE CONSENT OF THE COMPANY OR THE MANAGING UNDERWRITER.
(b)    Stop-Transfer Notices. Participant agrees that, in order to ensure
compliance with the restrictions referred to herein, the Company may issue
appropriate “stop transfer” instructions to its transfer agent, if any, and
that, if the Company transfers its own securities, it may make appropriate
notations to the same effect in its own records.
(c)    Refusal to Transfer. The Company shall not be required (i) to transfer on
its books any Shares that have been sold or otherwise transferred in violation
of any of the provisions of this Agreement or (ii) to treat as owner of such
Shares or to accord the right to vote or pay dividends to any purchaser or other
transferee to whom such Shares shall have been so transferred.
14.    Notices. Any notice, demand or request required or permitted to be given
by either the Company or Participant pursuant to the terms of this Agreement
shall be in writing and shall be deemed given when delivered personally or
deposited in the U.S. mail, First Class with postage prepaid, and

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addressed to the parties at the addresses of the parties set forth at the end of
this Agreement or such other address as a party may request by notifying the
other in writing.
Any notice to the Escrow Holder shall be sent to the Company’s address with a
copy to the other party not sending the notice.
15.    No Waiver. Either party’s failure to enforce any provision or provisions
of this Agreement shall not in any way be construed as a waiver of any such
provision or provisions, nor prevent that party from thereafter enforcing each
and every other provision of this Agreement. The rights granted both parties
herein are cumulative and shall not constitute a waiver of either party’s right
to assert all other legal remedies available to it under the circumstances.
16.    Successors and Assigns. The Company may assign any of its rights under
this Agreement to single or multiple assignees, and this Agreement shall inure
to the benefit of the successors and assigns of the Company. Subject to the
restrictions on transfer herein set forth, this Agreement shall be binding upon
Participant and his or her heirs, executors, administrators, successors and
assigns. The rights and obligations of Participant under this Agreement may only
be assigned with the prior written consent of the Company.
17.    Interpretation. Any dispute regarding the interpretation of this
Agreement shall be submitted by Participant or by the Company forthwith to the
Administrator, which shall review such dispute at its next regular meeting. The
resolution of such a dispute by the Administrator shall be final and binding on
all parties.
18.    Additional Documents. Participant agrees upon request to execute any
further documents or instruments necessary or desirable to carry out the
purposes or intent of this Agreement.
19.    Governing Law; Severability. This Agreement is governed by the internal
substantive laws, but not the choice of law rules, of Texas. In the event that
any provision hereof becomes or is declared by a court of competent jurisdiction
to be illegal, unenforceable or void, this Agreement shall continue in full
force and effect.
20.    Entire Agreement. The Plan is incorporated herein by reference. The Plan
and this Agreement (including the exhibits referenced herein) constitute the
entire agreement of the parties with respect to the subject matter hereof and
supersede in their entirety all prior undertakings and agreements of the Company
and Participant with respect to the subject matter hereof, and may not be
modified adversely to the Participant’s interest except by means of a writing
signed by the Company and Participant.
Participant acknowledges receipt of a copy of the Plan and represents that he or
she is familiar with the terms and provisions thereof, and hereby accepts this
Agreement subject to all of the terms and provisions thereof. Participant has
reviewed the Plan and this Agreement in their entirety, has had an opportunity
to obtain the advice of counsel prior to executing this Agreement and fully
understands all provisions of this Agreement. Participant hereby agrees to
accept as binding, conclusive and final all decisions or interpretations of the
Administrator upon any questions arising under the Plan or this

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Agreement. Participant further agrees to notify the Company upon any change in
the residence address indicated below.
(Signature page(s) to follow.)

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PARTICIPANT                    UPLAND SOFTWARE, INC.

/s/ Timothy Mattox        /s/ John T. McDonald    
Signature        By
Timothy Mattox        John T. McDonald    
Print Name        Print Name
Chief Executive Officer    
            Title

8001 Big View Dr., Austin, Texas 78730    
Residence Address

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EXHIBIT A
INVESTMENT REPRESENTATION STATEMENT

PARTICIPANT     :    TIMOTHY MATTOX
COMPANY    :    UPLAND SOFTWARE, INC.
SECURITY    :    COMMON STOCK
AMOUNT    :    500,000         SHARES
DATE            :    SEPTEMBER 2, 2014    
In connection with the purchase of the above-listed Securities, the undersigned
Participant represents to the Company the following:
(a)Participant is aware of the Company’s business affairs and financial
condition and has acquired sufficient information about the Company to reach an
informed and knowledgeable decision to acquire the Securities. Participant is
acquiring these Securities for investment for Participant’s own account only and
not with a view to, or for resale in connection with, any “distribution” thereof
within the meaning of the Securities Act of 1933, as amended (the “Securities
Act”).
(b)    Participant acknowledges and understands that the Securities constitute
“restricted securities” under the Securities Act and have not been registered
under the Securities Act in reliance upon a specific exemption therefrom, which
exemption depends upon, among other things, the bona fide nature of
Participant’s investment intent as expressed herein. In this connection,
Participant understands that, in the view of the Securities and Exchange
Commission, the statutory basis for such exemption may be unavailable if
Participant’s representation was predicated solely upon a present intention to
hold these Securities for the minimum capital gains period specified under tax
statutes, for a deferred sale, for or until an increase or decrease in the
market price of the Securities, or for a period of one year or any other fixed
period in the future. Participant further understands that the Securities must
be held indefinitely unless they are subsequently registered under the
Securities Act or an exemption from such registration is available. Participant
further acknowledges and understands that the Company is under no obligation to
register the Securities. Participant understands that the certificate evidencing
the Securities shall be imprinted with any legend required under applicable
state securities laws.
(c)    Participant is familiar with the provisions of Rule 701 and Rule 144,
each promulgated under the Securities Act, which, in substance, permit limited
public resale of “restricted securities” acquired, directly or indirectly from
the issuer thereof, in a non-public offering subject to the satisfaction of
certain conditions. Rule 701 provides that if the issuer qualifies under
Rule 701 at the time of the grant of the Restricted Stock Award to Participant,
the exercise shall be exempt from registration under the Securities Act. In the
event the Company becomes subject to the reporting requirements of Section 13 or
15(d) of the Securities Exchange Act of 1934, ninety (90) days thereafter (or
such longer period as any market stand-off agreement may require) the Securities
exempt under

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Rule 701 may be resold, subject to the satisfaction of the applicable conditions
specified by Rule 144, including in the case of affiliates (1) the availability
of certain public information about the Company, (2) the amount of Securities
being sold during any three (3) month period not exceeding specified
limitations, (3) the resale being made in an unsolicited “broker’s transaction”,
transactions directly with a “market maker” or “riskless principal transactions”
(as those terms are defined under the Securities Exchange Act of 1934) and
(4) the timely filing of a Form 144, if applicable.
In the event that the Company does not qualify under Rule 701 at the time of
grant of the Restricted Stock Award, then the Securities may be resold in
certain limited circumstances subject to the provisions of Rule 144, which may
require (i) the availability of current public information about the Company;
(ii) the resale to occur more than a specified period after the purchase and
full payment (within the meaning of Rule 144) for the Securities; and (iii) in
the case of the sale of Securities by an affiliate, the satisfaction of the
conditions set forth in sections (2), (3) and (4) of the paragraph immediately
above.
(d)    Participant further understands that in the event all of the applicable
requirements of Rule 701 or 144 are not satisfied, registration under the
Securities Act, compliance with Regulation A, or some other registration
exemption shall be required; and that, notwithstanding the fact that Rules 144
and 701 are not exclusive, the Staff of the Securities and Exchange Commission
has expressed its opinion that persons proposing to sell private placement
securities other than in a registered offering and otherwise than pursuant to
Rules 144 or 701 shall have a substantial burden of proof in establishing that
an exemption from registration is available for such offers or sales, and that
such persons and their respective brokers who participate in such transactions
do so at their own risk. Participant understands that no assurances can be given
that any such other registration exemption shall be available in such event.
PARTICIPANT
/s/ Timothy Mattox    

Signature
Timothy Mattox    

Print Name
9/2/2014    

Date

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EXHIBIT B-1
ASSIGNMENT SEPARATE FROM CERTIFICATE
FOR VALUE RECEIVED I, __________________________, hereby sell, assign and
transfer unto Upland Software, Inc. _____________ shares of the Common Stock of
Upland Software, Inc. standing in my name on the books of said corporation
represented by Certificate No. _____ herewith and do hereby irrevocably
constitute and appoint __________________________ to transfer the said stock on
the books of the within named corporation with full power of substitution in the
premises.
This Stock Assignment may be used only in accordance with the Restricted Stock
Purchase Agreement between Upland Software, Inc. and the undersigned dated
______________, _____ (the “Agreement”).

Dated: _______________,____        Signature: /s/ Timothy Mattox    

INSTRUCTIONS: Please do not fill in any blanks other than the signature line.
The purpose of this assignment is to enable the Company to exercise its
“repurchase option,” as set forth in the Agreement, without requiring additional
signatures on the part of the Participant.

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EXHIBIT B-2
JOINT ESCROW INSTRUCTIONS
September 2, 2014
Chief Financial Officer
Upland Software, Inc.
401 Congress Ave.
Suite 1850
Austin, TX 78701

Dear Mr. Hill:
As Escrow Agent for both Upland Software, Inc. (the “Company”), and the
undersigned purchaser of stock of the Company (the “Participant”), you are
hereby authorized and directed to hold the documents delivered to you pursuant
to the terms of that certain Restricted Stock Purchase Agreement (the
“Agreement”) between the Company and the undersigned, in accordance with the
following instructions:
1.In the event the Company and/or any assignee of the Company (referred to
collectively for convenience herein as the “Company”) exercises the Company’s
repurchase option set forth in the Agreement, the Company shall give to
Participant and you a written notice specifying the number of shares of stock to
be purchased, the purchase price, and the time for a closing hereunder at the
principal office of the Company. Participant and the Company hereby irrevocably
authorize and direct you to close the transaction contemplated by such notice in
accordance with the terms of said notice.
2.    At the closing, you are directed (a) to date the stock assignments
necessary for the transfer in question, (b) to fill in the number of shares
being transferred, and (c) to deliver the stock assignments, together with the
certificate evidencing the shares of stock to be transferred, to the Company or
its assignee, against the simultaneous delivery to you of the purchase price (by
cash, a check, or some combination thereof) for the number of shares of stock
being purchased pursuant to the exercise of the Company’s repurchase option.
3.    Participant irrevocably authorizes the Company to deposit with you any
certificates evidencing shares of stock to be held by you hereunder and any
additions and substitutions to said shares as defined in the Agreement.
Participant does hereby irrevocably constitute and appoint you as Participant’s
attorney-in-fact and agent for the term of this escrow to execute with respect
to such securities all documents necessary or appropriate to make such
securities negotiable and to complete any transaction herein contemplated,
including but not limited to the filing with any applicable state blue sky
authority of any required applications for consent to, or notice of transfer of,
the securities. Subject to the provisions of this paragraph 3, Participant shall
exercise all rights and privileges of a stockholder of the Company while the
stock is held by you.

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4.    Upon written request of the Participant, but no more than once per
calendar year, unless the Company’s repurchase option has been exercised, you
shall deliver to Participant a certificate or certificates representing so many
shares of stock as are not then subject to the Company’s repurchase option.
Within one hundred and twenty (120) days after cessation of Participant’s
continuous employment by or services to the Company, or any parent or subsidiary
of the Company, you shall deliver to Participant a certificate or certificates
representing the aggregate number of shares held or issued pursuant to the
Agreement and not purchased by the Company or its assignees pursuant to exercise
of the Company’s repurchase option.
5.    If at the time of termination of this escrow you should have in your
possession any documents, securities, or other property belonging to
Participant, you shall deliver all of the same to Participant and shall be
discharged of all further obligations hereunder.
6.    Your duties hereunder may be altered, amended, modified or revoked only by
a writing signed by all of the parties hereto.
7.    You shall be obligated only for the performance of such duties as are
specifically set forth herein and may rely and shall be protected in relying or
refraining from acting on any instrument reasonably believed by you to be
genuine and to have been signed or presented by the proper party or parties. You
shall not be personally liable for any act you may do or omit to do hereunder as
Escrow Agent or as attorney-in-fact for Participant while acting in good faith,
and any act done or omitted by you pursuant to the advice of your own attorneys
shall be conclusive evidence of such good faith.
8.    You are hereby expressly authorized to disregard any and all warnings
given by any of the parties hereto or by any other person or corporation,
excepting only orders or process of courts of law and are hereby expressly
authorized to comply with and obey orders, judgments or decrees of any court. In
case you obey or comply with any such order, judgment or decree, you shall not
be liable to any of the parties hereto or to any other person, firm or
corporation by reason of such compliance, notwithstanding any such order,
judgment or decree being subsequently reversed, modified, annulled, set aside,
vacated or found to have been entered without jurisdiction.
9.    You shall not be liable in any respect on account of the identity,
authorities or rights of the parties executing or delivering or purporting to
execute or deliver the Agreement or any documents or papers deposited or called
for hereunder.
10.    You shall not be liable for the outlawing of any rights under the Statute
of Limitations with respect to these Joint Escrow Instructions or any documents
deposited with you.
11.    You shall be entitled to employ such legal counsel and other experts as
you may deem necessary properly to advise you in connection with your
obligations hereunder, may rely upon the advice of such counsel, and may pay
such counsel reasonable compensation therefor.
12.    Your responsibilities as Escrow Agent hereunder shall terminate if you
shall cease to be an officer or agent of the Company or if you shall resign by
written notice to each party. In the event of any such termination, the Company
shall appoint a successor Escrow Agent.

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13.    If you reasonably require other or further instruments in connection with
these Joint Escrow Instructions or obligations in respect hereto, the necessary
parties hereto shall join in furnishing such instruments.
14.    It is understood and agreed that should any dispute arise with respect to
the delivery and/or ownership or right of possession of the securities held by
you hereunder, you are authorized and directed to retain in your possession
without liability to anyone all or any part of said securities until such
disputes shall have been settled either by mutual written agreement of the
parties concerned or by a final order, decree or judgment of a court of
competent jurisdiction after the time for appeal has expired and no appeal has
been perfected, but you shall be under no duty whatsoever to institute or defend
any such proceedings.
15.    Any notice required or permitted hereunder shall be given in writing and
shall be deemed effectively given upon personal delivery or upon deposit in the
United States Post Office, by registered or certified mail with postage and fees
prepaid, addressed to each of the other parties thereunto entitled at the
following addresses or at such other addresses as a party may designate by ten
(10) days advance written notice to each of the other parties hereto.
16.    By signing these Joint Escrow Instructions, you become a party hereto
only for the purpose of said Joint Escrow Instructions; you do not become a
party to the Agreement.
17.    This instrument shall be binding upon and inure to the benefit of the
parties hereto, and their respective successors and permitted assigns.
18.    These Joint Escrow Instructions shall be governed by the internal
substantive laws, but not the choice of law rules, of Texas.
(Signature page(s) to follow.)

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PARTICIPANT        UPLAND SOFTWARE, INC.

/s/ Timothy Mattox        /s/ John T. McDonald    
Signature        By
Timothy Mattox        John T. McDonald    
Print Name        Print Name
Chief Executive Officer    
            Title

8001 Big View Dr., Austin, Texas 78730    
Residence Address
ESCROW AGENT
/s/ Michael D. Hill    
Chief Financial Officer
Dated: 9/2/2014                

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EXHIBIT B-3

SPOUSAL CONSENT

I, Christine Mattox, spouse of Timothy Mattox, have read and approve of the
foregoing Restricted Stock Purchase Agreement, dated as of September 2, 2014,
together with all exhibits and attachments thereto (collectively, the
“Agreement”), by and between my spouse and Upland Software, Inc., a Delaware
corporation (the “Company”). In consideration of the Company’s granting of the
right to Timothy Mattox to purchase 500,000 shares of Common Stock of the
Company as set forth in the Agreement, I hereby appoint Timothy Mattox as my
attorney-in-fact in respect to the exercise or waiver of any rights under the
Agreement, and agree to be bound by the provisions of the Agreement insofar as I
may have any rights in said Agreement or any shares issued pursuant thereto
under the community property laws of the State of Texas, or under similar laws
relating to marital property in effect in the state of our residence as of the
date of the signing of the foregoing Agreement.
Dated: 11/2/2014_______________________

/s/ Christine Mattox    
(Signature)
Christine Mattox     
(Print Name)

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