Document:

EX-10.3.1

 Exhibit 10.3.1 

AMENDED AND RESTATED UPLAND SOFTWARE, INC. 

2010 STOCK PLAN 
 (as
amended September 2, 2014) 
 1. Purposes of the Plan. The purposes of this Plan are to attract and retain the
best available personnel for positions of substantial responsibility, to provide additional incentive to Employees, Directors and Consultants and to promote the success of the Company’s business. The Plan permits the grant of Options,
Restricted Stock and Restricted Stock Units as the Administrator may determine. 
 2. Definitions. As used herein, the following
definitions shall apply: 
 (a) “Administrator” means the Board or any of its Committees as shall be administering the Plan
in accordance with Section 4 hereof. 
 (b) “Applicable Laws” means the requirements relating to the administration of
equity compensation plans under U.S. state corporate laws, U.S. federal and state securities laws, the Code, any stock exchange or quotation system on which the Common Stock is listed or quoted and the applicable laws of any other country or
jurisdiction where Awards are granted under the Plan. 
 (c) “Award” means, individually or collectively, a grant under the
Plan of Options, Restricted Stock or Restricted Stock Units. 
 (d) “Award Agreement” means the written or electronic
agreement setting forth the terms and provisions applicable to each Award granted under the Plan. The Award Agreement is subject to the terms and conditions of the Plan. 

(e) “Board” means the Board of Directors of the Company. 

(f) “Change in Control” means the occurrence of any of the following events: 

(i) Change in Ownership of the Company. A change in the ownership of the Company which occurs on the date that any one person, or more
than one person acting as a group (“Person”), acquires ownership of the stock of the Company that, together with the stock held by such Person, constitutes more than 50% of the total voting power of the stock of the Company, except that
any change in the ownership of the stock of the Company as a result of a private financing of the Company that is approved by the Board will not be considered a Change in Control; or 

(ii) Change in Effective Control of the Company. If the Company has a class of securities registered pursuant to Section 12 of the
Exchange Act, a change in the effective control of the Company which occurs on the date that a majority of members of the Board is replaced during any twelve (12) month period by Directors whose appointment or election is not endorsed by a
majority of the members of the Board prior to the date of the appointment or election. For purposes of this clause (ii), if any Person is considered to be in effective control of the Company, the acquisition of additional control of the Company by
the same Person will not be considered a Change in Control; or 

 (iii) Change in Ownership of a Substantial Portion of the Company’s Assets. A change
in the ownership of a substantial portion of the Company’s assets which occurs on the date that any Person acquires (or has acquired during the twelve (12) month period ending on the date of the most recent acquisition by such person or
persons) assets from the Company that have a total gross fair market value equal to or more than 50% of the total gross fair market value of all of the assets of the Company immediately prior to such acquisition or acquisitions. For purposes of this
subsection (iii), gross fair market value means the value of the assets of the Company, or the value of the assets being disposed of, determined without regard to any liabilities associated with such assets. 

For purposes of this Section 2(f), persons will be considered to be acting as a group if they are owners of a corporation that enters
into a merger, consolidation, purchase or acquisition of stock, or similar business transaction with the Company. 
 Notwithstanding the
foregoing, a transaction shall not be deemed a Change in Control unless the transaction qualifies as a change in control event within the meaning of Section 409A of the Code, as it has been and may be amended from time to time, and any proposed
or final Treasury Regulations and Internal Revenue Service guidance that has been promulgated or may be promulgated thereunder from time to time. 

Further and for the avoidance of doubt, a transaction shall not constitute a Change in Control if: (i) its sole purpose is to change the
state of the Company’s incorporation, or (ii) its sole purpose is to create a holding company that shall be owned in substantially the same proportions by the persons who held the Company’s securities immediately before such
transaction. 
 (g) “Code” means the Internal Revenue Code of 1986, as amended. Any reference to a section of the Code
herein shall be a reference to any successor or amended section of the Code. 
 (h) “Committee” means a committee of
Directors or of other individuals satisfying Applicable Laws appointed by the Board, or by the compensation committee of the Board, in accordance with Section 4 hereof. 

(i) “Common Stock” means the Common Stock of the Company. 

(j) “Company” means Upland Software, Inc. (f/k/a Silverback Enterprise Group, Inc.), a Delaware corporation. 

(k) “Consultant” means any person who is engaged by the Company or any Parent or Subsidiary to render consulting or advisory
services to such entity. 
 (l) “Director” means a member of the Board. 

(m) “Disability” means total and permanent disability as defined in Section 22(e)(3) of the Code. 

  
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 (n) “Employee” means any person, including officers and Directors, employed by
the Company or any Parent or Subsidiary of the Company. Neither service as a Director nor payment of a director’s fee by the Company shall be sufficient to constitute “employment” by the Company. 

(o) “Exchange Act” means the Securities Exchange Act of 1934, as amended. 

(p) “Exchange Program” means a program under which (i) outstanding Options are surrendered or cancelled in exchange for
Options of the same type (which may have lower or higher exercise prices and different terms), Options of a different type, and/or cash, and/or (ii) the exercise price of an outstanding Option is reduced. The terms and conditions of any
Exchange Program shall be determined by the Administrator in its sole discretion. 
 (q) “Fair Market Value” means, as of
any date, the value of Common Stock determined as follows: 
 (i) If the Common Stock is listed on any established stock exchange or a
national market system, including without limitation the Nasdaq Global Market, the Nasdaq Global Select Market or the Nasdaq Capital Market, its Fair Market Value shall be the closing sales price for such stock (or, if no closing sales price was
reported on that date, as applicable, on the last trading date such closing sales price was reported) as quoted on such exchange or system on the day of determination, as reported in The Wall Street Journal or such other source as the
Administrator deems reliable; 
 (ii) If the Common Stock is regularly quoted by a recognized securities dealer but selling prices are not
reported, its Fair Market Value shall be the mean between the high bid and low asked prices for the Common Stock on the day of determination (or, if no bids and asks were reported on that date, as applicable, on the last trading date such bids and
asks were reported); or 
 (iii) In the absence of an established market for the Common Stock, the Fair Market Value thereof shall be
determined in good faith by the Administrator. 
 (r) “Incentive Stock Option” means an Option that by its terms qualifies
and is otherwise intended to qualify as an incentive stock option within the meaning of Section 422 of the Code and the regulations promulgated thereunder. 

(s) “Nonstatutory Stock Option” means an Option that by its terms does not qualify or is not intended to qualify as an
Incentive Stock Option. 
 (t) “Option” means a stock option granted pursuant to the Plan. 

(u) “Parent” means a “parent corporation,” whether now or hereafter existing, as defined in Section 424(e) of
the Code. 
 (v) “Participant” means the holder of an outstanding Award. 

(w) “Plan” means this 2010 Stock Plan. 

  
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 (x) “Restricted Stock” means Shares issued pursuant to a Restricted Stock award
under Section 7 of the Plan, or issued pursuant to the early exercise of an Option. 
 (y) “Restricted Stock Purchase
Agreement” means a written or electronic agreement between the Company and the Participant evidencing the terms and restrictions applying to Shares purchased under a Restricted Stock award. The Restricted Stock Purchase Agreement is subject
to the terms and conditions of the Plan and the notice of grant. 
 (z) “Restricted Stock Unit” means a bookkeeping entry
representing an amount equal to the Fair Market Value of one Share, granted pursuant to Section 9. Each Restricted Stock Unit represents an unfunded and unsecured obligation of the Company. 

(aa) “Securities Act” means the Securities Act of 1933, as amended. 

(bb) “Service Provider” means an Employee, Director or Consultant. 

(cc) “Share” means a share of the Common Stock, as adjusted in accordance with Section 12 below. 

(dd) “Subsidiary” means a “subsidiary corporation,” whether now or hereafter existing, as defined in
Section 424(f) of the Code. 
 3. Stock Subject to the Plan. Subject to the provisions of Section 12 of
the Plan, the maximum aggregate number of Shares that may be subject to Awards and sold under the Plan is 7,277,992 Shares. The Shares may be authorized but unissued, or reacquired Common Stock. 

If an Award expires or becomes unexercisable without having been exercised in full, is surrendered pursuant to an Exchange Program, or with
respect to Restricted Stock Units is forfeited due to failure to vest, the unpurchased Shares (or with respect to Restricted Stock Units, the forfeited Shares) that were subject thereto shall become available for future grant or sale under the Plan
(unless the Plan has terminated). However, Shares that have actually been issued under the Plan, upon exercise of an Award, shall not be returned to the Plan and shall not become available for future distribution under the Plan, except that if
unvested Shares of Restricted Stock are repurchased by the Company at their original purchase price, such Shares shall become available for future grant under the Plan. Notwithstanding the foregoing and, subject to adjustment provided in
Section 12, the maximum number of Shares that may be issued upon the exercise of Incentive Stock Options shall equal the aggregate Share number stated in the first paragraph of this Section, plus, to the extent allowable under Section 422
of the Code, any Shares that become available for issuance under the Plan under this second paragraph of this Section. 
 4.
Administration of the Plan. 
 (a) Administrator. The Plan shall be administered by the Board or a Committee
appointed by the Board, which Committee shall be constituted to comply with Applicable Laws. 
 (b)
Powers of the Administrator. Subject to the provisions of the Plan and, in the case of a Committee, the specific duties delegated by the Board to such Committee, and subject to the approval of any relevant authorities, the
Administrator shall have the authority in its discretion: 

  
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 (i) to determine the Fair Market Value; 

(ii) to select the Service Providers to whom Awards may from time to time be granted hereunder; 

(iii) to determine the number of Shares to be covered by each such Award granted hereunder; 

(iv) to approve forms of agreement for use under the Plan; 

(v) to determine the terms and conditions of any Award granted hereunder. Such terms and conditions include, but are not limited to, the
exercise price, the time or times when Awards may be exercised (which may be based on performance criteria), any vesting acceleration or waiver of forfeiture restrictions, and any restriction or limitation regarding any Award or the Common Stock
relating thereto, based in each case on such factors as the Administrator, in its sole discretion, shall determine; 
 (vi) to institute an
Exchange Program; 
 (vii) to prescribe, amend and rescind rules and regulations relating to the Plan, including rules and regulations
relating to sub-plans established for the purpose of satisfying applicable foreign laws; 
 (viii) to modify or amend each Award (subject to
Section 20(c) of the Plan) including but not limited to the discretionary authority to extend the post-termination exercise period of Awards and to extend the maximum term of an Option (subject to Section 6(a) regarding Incentive Stock
Options); 
 (ix) to authorize any person to execute on behalf of the Company any instrument required to effect the grant of an Award
previously granted by the Administrator; and 
 (x) to construe and interpret the terms of the Plan and Awards granted pursuant to the Plan.

 (c) Effect of Administrator’s Decision. All decisions, determinations and interpretations of the Administrator
shall be final and binding on all Participants. 
 5. Eligibility. Nonstatutory Stock Options, Restricted Stock and Restricted Stock
Units may be granted to Service Providers. Incentive Stock Options may be granted only to Employees. 
 6. Stock Options. 

(a) Term of Option. The term of each Option shall be stated in the Award Agreement; provided, however, that the term shall be no more
than ten (10) years from the date of grant thereof. In the case of an Incentive Stock Option granted to a Participant who, at the time the Option is granted, owns stock representing more than ten percent (10%) of the voting power of all
classes of stock of the Company or any Parent or Subsidiary, the term of the Option shall be five (5) years from the date of grant or such shorter term as may be provided in the Award Agreement. 

  
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 (b) Option Exercise Price and Consideration. 

(i) Exercise Price. The per share exercise price for the Shares to be issued upon exercise of an Option shall be such price as is
determined by the Administrator, but shall be subject to the following: 
 (A) In the case of an Incentive Stock Option 

a) granted to an Employee who, at the time of grant of such Option, owns stock representing more than ten percent (10%) of the voting
power of all classes of stock of the Company or any Parent or Subsidiary, the exercise price shall be no less than one hundred and ten percent (110%) of the Fair Market Value per Share on the date of grant. 

b) granted to any other Employee, the per Share exercise price shall be no less than one hundred percent (100%) of the Fair Market Value
per Share on the date of grant. 
 (B) In the case of a Nonstatutory Stock Option, the per Share exercise price shall be no less than one
hundred percent (100%) of the Fair Market Value per Share on the date of grant. 
 (C) Notwithstanding the foregoing, Options may be
granted with a per Share exercise price other than as required above in accordance with and pursuant to a transaction described in Section 424 of the Code. 

(ii) Forms of Consideration. The consideration to be paid for the Shares to be issued upon exercise of an Option, including the method
of payment, shall be determined by the Administrator (and, in the case of an Incentive Stock Option, shall be determined at the time of grant). Such consideration may consist of, without limitation, (1) cash, (2) check, (3) promissory
note, to the extent permitted by Applicable Laws, (4) other Shares, provided that such Shares have a Fair Market Value on the date of surrender equal to the aggregate exercise price of the Shares as to which such Option shall be exercised and
provided that accepting such Shares, in the sole discretion of the Administrator, shall not result in any adverse accounting consequences to the Company, (5) consideration received by the Company under a cashless exercise program implemented by
the Company in connection with the Plan, (6) such other consideration and method of payment for the issuance of Shares to the extent permitted by Applicable Laws, or (7) any combination of the foregoing methods of payment. In making its
determination as to the type of consideration to accept, the Administrator shall consider if acceptance of such consideration may be reasonably expected to benefit the Company. 

(c) Exercise of Option. 

(i) Procedure for Exercise; Rights as a Stockholder. Any Option granted hereunder shall be exercisable according to the terms
hereof at such times and under such conditions as determined by the Administrator and set forth in the Award Agreement. An Option may not be exercised for a fraction of a Share. 

  
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 An Option shall be deemed exercised when the Company receives (i) written or electronic
notice of exercise (in accordance with the Award Agreement) from the person entitled to exercise the Option, and (ii) full payment for the Shares with respect to which the Option is exercised, together with any applicable withholding taxes.
Full payment may consist of any consideration and method of payment authorized by the Administrator and permitted by the Award Agreement and the Plan. Shares issued upon exercise of an Option shall be issued in the name of the Participant or, if
requested by the Participant, in the name of the Participant and his or her spouse. Until the Shares are issued (as evidenced by the appropriate entry on the books of the Company or of a duly authorized transfer agent of the Company), no right to
vote or receive dividends or any other rights as a stockholder shall exist with respect to the Shares, notwithstanding the exercise of the Option. The Company shall issue (or cause to be issued) such Shares promptly after the Option is exercised. No
adjustment shall be made for a dividend or other right for which the record date is prior to the date the Shares are issued, except as provided in Section 12 of the Plan. 

Exercise of an Option in any manner shall result in a decrease in the number of Shares thereafter available, both for purposes of the Plan and
for sale under the Option, by the number of Shares as to which the Option is exercised. 
 (ii) Termination of Relationship as a
Service Provider. If a Participant ceases to be a Service Provider, such Participant may exercise his or her Option within such period of time as is specified in the Award Agreement, to the extent that the Option is vested on the date of
termination (but in no event later than the expiration of the term of the Option as set forth in the Award Agreement). In the absence of a specified time in the Award Agreement, the Option shall remain exercisable for three (3) months following
the Participant’s termination. Unless the Administrator provides otherwise, if on the date of termination the Participant is not vested as to his or her entire Option, the Shares covered by the unvested portion of the Option shall revert to the
Plan. If, after termination, the Participant does not exercise his or her Option within the time specified by the Administrator, the Option shall terminate, and the Shares covered by such Option shall revert to the Plan. 

(iii) Disability of Participant. If a Participant ceases to be a Service Provider as a result of the Participant’s Disability, the
Participant may exercise his or her Option within such longer period of time as is specified in the Award Agreement, to the extent the Option is vested on the date of termination (but in no event later than the expiration of the term of such Option
as set forth in the Award Agreement). In the absence of a specified time in the Award Agreement, the Option shall remain exercisable for twelve (12) months following the Participant’s termination. Unless the Administrator provides
otherwise, if on the date of termination the Participant is not vested as to his or her entire Option, the Shares covered by the unvested portion of the Option shall revert to the Plan. If, after termination, the Participant does not exercise his or
her Option within the time specified herein, the Option shall terminate, and the Shares covered by such Option shall revert to the Plan. 

(iv) Death of Participant. If a Participant dies while a Service Provider, the Option may be exercised within such longer
period of time as is specified in the Award Agreement, to the extent that the Option is vested on the date of death (but in no event later than the expiration of the term of such Option as set forth in the Award Agreement) by the Participant’s
designated beneficiary, provided such beneficiary has been designated prior to the Participant’s death in a form 

  
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acceptable to the Administrator. If no such beneficiary has been designated by the Participant, then such Option may be exercised by the personal representative of the Participant’s estate
or by the person(s) to whom the Option is transferred pursuant to the Participant’s will or in accordance with the laws of descent and distribution. In the absence of a specified time in the Award Agreement, the Option shall remain exercisable
for twelve (12) months following the Participant’s termination. If, at the time of death, the Participant is not vested as to his or her entire Option, the Shares covered by the unvested portion of the Option shall immediately revert to
the Plan. If the Option is not so exercised within the time specified herein, the Option shall terminate, and the Shares covered by such Option shall revert to the Plan. 

(v) Incentive Stock Option Limit. Each Option shall be designated in the Award Agreement as either an Incentive Stock Option or a
Nonstatutory Stock Option. However, notwithstanding such designation, to the extent that the aggregate Fair Market Value of the Shares with respect to which Incentive Stock Options are exercisable for the first time by the Participant during any
calendar year (under all plans of the Company and any Parent or Subsidiary) exceeds one hundred thousand dollars ($100,000), such Options shall be treated as Nonstatutory Stock Options. For purposes of this Section 6(c)(v), Incentive Stock
Options shall be taken into account in the order in which they were granted. The Fair Market Value of the Shares shall be determined as of the time the Option with respect to such Shares is granted. 

7. Restricted Stock. 
 (a)
Rights to Purchase. Restricted Stock may be issued either alone, in addition to, or in tandem with other awards granted under the Plan and/or cash awards made outside of the Plan. After the Administrator determines that it shall offer
Restricted Stock under the Plan, it shall advise the offeree in writing or electronically of the terms, conditions and restrictions related to the offer, including the number of Shares that such person shall be entitled to purchase, the price to be
paid (if any), and the time within which such person must accept such offer. 
 (b) Repurchase Option. Unless the Administrator
determines otherwise, the Restricted Stock Purchase Agreement shall grant the Company a repurchase option exercisable within ninety (90) days of the voluntary or involuntary termination of the purchaser’s service with the Company for any
reason (including death or Disability). Unless the Administrator provides otherwise, the purchase price for Shares repurchased pursuant to the Restricted Stock Purchase Agreement shall be the original price paid by the purchaser and may be paid by
cancellation of any indebtedness of the purchaser to the Company. The repurchase option shall lapse at such rate as the Administrator may determine. 

(c) Other Provisions. The Restricted Stock Purchase Agreement shall contain such other terms, provisions and conditions not inconsistent
with the Plan as may be determined by the Administrator in its sole discretion. 
 (d) Rights as a Stockholder. Once the Restricted
Stock is purchased or otherwise issued, the purchaser shall have rights equivalent to those of a stockholder and shall be a stockholder when his or her purchase is entered upon the records of the duly authorized transfer agent of the Company. No
adjustment shall be made for a dividend or other right for which the record date is prior to the date the Restricted Stock is purchased or otherwise issued, except as provided in Section 12 of the Plan. 

  
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 8. Restricted Stock Units. 

(a) Grant. Restricted Stock Units may be granted at any time and from time to time as determined by the Administrator. After the
Administrator determines that it will grant Restricted Stock Units, it will advise the Participant in an Award Agreement of the terms, conditions, and restrictions related to the grant, including the number of Restricted Stock Units. 

(b) Vesting Criteria and Other Terms. The Administrator will set vesting criteria in its discretion, which, depending on the extent to
which the criteria are met, will determine the number of Restricted Stock Units that will be paid out to the Participant. The Administrator may set vesting criteria based upon the achievement of Company-wide, business unit, or individual goals
(including, but not limited to, continued employment or service), or any other basis determined by the Administrator in its discretion. 

(c) Earning Restricted Stock Units. Upon meeting the applicable vesting criteria, the Participant will be entitled to receive a payout
as determined by the Administrator. Notwithstanding the foregoing, at any time after the grant of Restricted Stock Units, the Administrator, in its sole discretion, may reduce or waive any vesting criteria that must be met to receive a payout. 

(d) Form and Timing of Payment. Payment of earned Restricted Stock Units will be made as soon as practicable after the date(s)
determined by the Administrator and set forth in the Award Agreement. The Administrator, in its sole discretion, may settle earned Restricted Stock Units in cash, Shares, or a combination of both. 

(e) Cancellation. On the date set forth in the Award Agreement, all unearned Restricted Stock Units will be forfeited to the Company.

 9. Tax Withholding. Prior to the delivery of any Shares pursuant to an Award (or exercise thereof), the Company shall have the
power and the right to deduct or withhold, or require a Participant to remit to the Company, an amount sufficient to satisfy federal, state, local, foreign or other taxes (including the Participant’s FICA obligation) required to be withheld
with respect to such Award (or exercise thereof). The Administrator, in its sole discretion and pursuant to such procedures as it may specify from time to time, shall determine in what manner it shall allow a Participant to satisfy such tax
withholding obligation and may permit the Participant to satisfy such tax withholding obligation, in whole or in part by one (1) or more of the following: (a) paying cash (or by check), (b) electing to have the Company withhold
otherwise deliverable Shares having a Fair Market Value equal to the minimum amount statutorily required to be withheld, or (c) selling a sufficient number of such Shares otherwise deliverable to a Participant through such means as the Company
may determine in its sole discretion (whether through a broker or otherwise) equal to the minimum amount statutorily required to be withheld. 

10. Limited Transferability of Awards. Unless determined otherwise by the Administrator, Awards may not be sold, pledged,
assigned, hypothecated, transferred, or disposed of in any manner other than by will or the laws of descent and distribution, and may be exercised during the lifetime of the Participant, only by the Participant. 

  
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 11. Leaves of Absence; Transfers. 

(a) Unless the Administrator provides otherwise, or except as otherwise required by Applicable Laws, vesting of Awards granted hereunder shall
be suspended during any unpaid leave of absence. 
 (b) A Service Provider shall not cease to be a Service Provider in the case of
(i) any leave of absence approved by the Company, or (ii) transfers between locations of the Company or between the Company, its Parent, any Subsidiary, or any successor. 

(c) For purposes of Incentive Stock Options, no such leave may exceed three (3) months, unless reemployment upon expiration of such leave
is guaranteed by statute or contract. If reemployment upon expiration of a leave of absence approved by the Company is not so guaranteed, then six (6) months following the first
(1st) day of such leave, any Incentive Stock Option held by the Participant shall cease to be treated as an Incentive Stock Option and shall be treated for tax purposes as a Nonstatutory
Stock Option. 
 12. Adjustments; Dissolution or Liquidation; Merger or Change in Control. 

(a) Adjustments. In the event that any dividend or other distribution (whether in the form of cash, Shares, other securities, or other
property), recapitalization, stock split, reverse stock split, reorganization, merger, consolidation, split-up, spin-off, combination, repurchase, or exchange of Shares or other securities of the Company, or other change in the corporate structure
of the Company affecting the Shares occurs, the Administrator, in order to prevent diminution or enlargement of the benefits or potential benefits intended to be made available under the Plan, shall adjust the number and class of Shares that may be
delivered under the Plan and/or the number, class, and price of Shares covered by each outstanding Award. 
 (b) Dissolution or
Liquidation. In the event of the proposed dissolution or liquidation of the Company, the Administrator shall notify each Participant as soon as practicable prior to the effective date of such proposed transaction. To the extent it has not been
previously exercised, an Award shall terminate immediately prior to the consummation of such proposed action. 
 (c) Merger or Change in
Control. In the event of a merger or Change in Control, each outstanding Award shall be treated as the Administrator determines, including, without limitation, that each Award be assumed or an equivalent award substituted by the successor
corporation or a Parent or Subsidiary of the successor corporation. The Administrator shall not be required to treat all Awards similarly in the transaction. 

Notwithstanding the foregoing, in the event of a Change in Control in which the successor corporation does not assume or substitute for the
Award, the Participant shall fully vest in and have the right to exercise his or her outstanding Awards, including Shares as to which such Award would not otherwise be vested or exercisable, and restrictions on all of the Participant’s
Restricted Stock and Restricted Stock Units shall lapse. In addition, if an Award is not assumed or substituted in the event of a merger or Change in Control, the Administrator shall notify the 

 
Participant in writing or electronically that the Award shall be fully vested and exercisable for a period of time determined by the Administrator in its sole discretion, and any Award not
assumed or substituted for shall terminate upon the expiration of such period for no consideration, unless otherwise determined by the Administrator. 

For the purposes of this Section 12(c), the Award shall be considered assumed if, following the merger or Change in Control, the option or
right confers the right to purchase or receive, for each Share subject to the Award immediately prior to the merger or Change in Control, the consideration (whether stock, cash, or other securities or property) received in the merger or Change in
Control by holders of Common Stock for each Share held on the effective date of the transaction (and if holders were offered a choice of consideration, the type of consideration chosen by the holders of a majority of the outstanding Shares);
provided, however, that if such consideration received in the merger or Change in Control is not solely common stock of the successor corporation or its Parent, the Administrator may, with the consent of the successor corporation, provide for the
consideration to be received upon the exercise of the Award, for each Share subject to the Award, to be solely common stock of the successor corporation or its Parent equal in fair market value to the per share consideration received by holders of
common stock in the merger or Change in Control. 
 13. Time of Granting Awards. The date of grant of an Award shall,
for all purposes, be the date on which the Administrator makes the determination granting such Award, or such later date as is determined by the Administrator. Notice of the determination shall be given to each Service Provider to whom an Award is
so granted within a reasonable time after the date of such grant. 
 14. No Effect on Employment or Service. Neither the Plan nor any
Award shall confer upon any participant any right with respect to continuing the Participant’s relationship as a Service Provider with the Company, nor shall it interfere in any way with his or her right or the Company’s right to terminate
such relationship at any time, with or without cause, and with or without notice. 
 15.
Conditions Upon Issuance of Shares. 
 (a) Legal Compliance. Shares shall not be issued pursuant to the
exercise of an Award unless the exercise of such Award and the issuance and delivery of such Shares shall comply with Applicable Laws and shall be further subject to the approval of counsel for the Company with respect to such compliance. 

(b) Investment Representations. As a condition to the exercise of an Award, the Administrator may in its discretion require the person
exercising such Award to represent and warrant at the time of any such exercise that the Shares are being purchased only for investment and without any present intention to sell or distribute such Shares. 

16. Inability to Obtain Authority. The inability of the Company to obtain authority from any regulatory body having jurisdiction, which
authority is deemed by the Company’s counsel to be necessary to the lawful issuance and sale of any Shares hereunder, shall relieve the Company of any liability in respect of the failure to issue or sell such Shares as to which such requisite
authority shall not have been obtained. 

  
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 17. Reservation of Shares. The Company, during the term of this Plan, shall at
all times reserve and keep available such number of Shares as shall be sufficient to satisfy the requirements of the Plan. 
 18.
Stockholder Approval. The Plan shall be subject to approval by the stockholders of the Company within twelve (12) months after the date the Plan is adopted. Such stockholder approval shall be obtained in the degree and manner required
under Applicable Laws. 
 19. Term of Plan. Subject to stockholder approval in accordance with Section 18, the Plan
shall become effective upon its adoption by the Board. Unless sooner terminated under Section 20, it shall continue in effect for a term of ten (10) years from the later of (a) the effective date of the Plan, or (b) the earlier
of the most recent Board or stockholder approval of an increase in the number of Shares reserved for issuance under the Plan. 
 20.
Amendment and Termination of the Plan. 
 (a) Amendment and Termination. The Board may at any time
amend, alter, suspend or terminate the Plan. 
 (b) Stockholder Approval. The Board shall obtain stockholder approval of any Plan
amendment to the extent necessary and desirable to comply with Applicable Laws. 
 (c)
Effect of Amendment or Termination. No amendment, alteration, suspension or termination of the Plan shall impair the rights of any Participant, unless mutually agreed otherwise between the Participant and the
Administrator, which agreement must be in writing (which may include e-mail) and signed by the Participant and the Company. Termination of the Plan shall not affect the Administrator’s ability to exercise the powers granted to it hereunder with
respect to Options granted under the Plan prior to the date of such termination. 

  
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 APPENDIX A 

TO 
 UPLAND SOFTWARE, INC.
2010 STOCK PLAN 
 (for California residents only, to the extent required by 25102(o)) 

This Appendix A to the Upland Software, Inc. 2010 Stock Plan shall apply only to the Participants who are residents of the State of California
and who are receiving an Award under the Plan. Capitalized terms contained herein shall have the same meanings given to them in the Plan, unless otherwise provided by this Appendix A. Notwithstanding any provisions contained in the Plan to the
contrary and to the extent required by Applicable Laws, the following terms shall apply to all Awards granted to residents of the State of California, until such time as the Administrator amends this Appendix A or the Administrator otherwise
provides. 
 (a) The term of each Option shall be stated in the Award Agreement, provided, however, that the term shall be no more than
ten (10) years from the date of grant thereof. 
 (b) Unless determined otherwise by the Administrator, Awards may not be sold, pledged,
assigned, hypothecated, or otherwise transferred in any manner other than by will or by the laws of descent and distribution, and may be exercised, during the lifetime of the Participant, only by the Participant. If the Administrator makes an Award
transferable, such Award may only be transferred (i) by will, (ii) by the laws of descent and distribution, or (iii) as permitted by Rule 701 of the Securities Act of 1933, as amended (the “Securities Act”). 

(c) If a Participant ceases to be a Service Provider, such Participant may exercise his or her Option within such period of time as specified
in the Award Agreement, which shall not be less than thirty (30) days following the date of the Participant’s termination, to the extent that the Option is vested on the date of termination (but in no event later than the expiration of the
term of the Option as set forth in the Award Agreement). In the absence of a specified time in the Award Agreement, the Option shall remain exercisable for three (3) months following the Participant’s termination. 

(d) If a Participant ceases to be a Service Provider as a result of the Participant’s Disability, the Participant may exercise his or her
Option within such period of time as specified in the Award Agreement, which shall not be less than six (6) months following the date of the Participant’s termination, to the extent the Option is vested on the date of termination (but in
no event later than the expiration of the term of such Option as set forth in the Award Agreement). In the absence of a specified time in the Award Agreement, the Option shall remain exercisable for twelve (12) months following the
Participant’s termination. 
 (e) If a Participant dies while a Service Provider, the Option may be exercised within such period of time
as specified in the Award Agreement, which shall not be less than six (6) months following the date of the Participant’s death, to the extent the Option is vested on the date of death (but in no event later than the expiration of the term
of such Option as set forth in the Award Agreement) by the Participant’s designated beneficiary, personal representative, or by the person(s) 

 
to whom the Option is transferred pursuant to the Participant’s will or in accordance with the laws of descent and distribution. In the absence of a specified time in the Award Agreement,
the Option shall remain exercisable for twelve (12) months following the Participant’s termination. 
 (f) No Award shall be
granted to a resident of California more than ten (10) years after the earlier of the date of adoption of the Plan or the date the Plan is approved by the stockholders. 

(g) In the event that any dividend or other distribution (whether in the form of cash, Shares, other securities, or other property),
recapitalization, stock split, reverse stock split, reorganization, merger, consolidation, split-up, spin-off, combination, repurchase, or exchange of Shares or other securities of the Company, or other change in the corporate structure of the
Company affecting the Shares occurs, the Administrator, in order to prevent diminution or enlargement of the benefits or potential benefits intended to be made available under the Plan, will adjust the number and class of Shares that may be
delivered under the Plan and/or the number, class, and price of Shares covered by each outstanding Award; provided, however, that the Administrator will make such adjustments to an Award required by Section 25102(o) of the California
Corporations Code to the extent the Company is relying upon the exemption afforded thereby with respect to the Award. 
 (h) This Appendix A
shall be deemed to be part of the Plan and the Administrator shall have the authority to amend this Appendix A in accordance with Section 20 of the Plan. 

  
 -2-EX-10.4

 Exhibit 10.4 

UPLAND SOFTWARE, INC. 

2010 STOCK PLAN 
 STOCK
OPTION AGREEMENT 
 Unless otherwise defined herein, the terms defined in the 2010 Stock Plan (the “Plan”) shall have the same
defined meanings in this Stock Option Agreement (the “Option Agreement”). 
 I. NOTICE OF STOCK OPTION GRANT 

Name:                     

 The undersigned Participant has been granted an Option to purchase Common Stock of the Company, subject to the terms and conditions of
the Plan and this Option Agreement, as follows: 
  

			
	Date of Grant:	  	                    
		
	Vesting Commencement Date:	  	                    
		
	Exercise Price per Share:	  	US$                    
		
	Total Number of Shares Granted:	  	                    
		
	Total Exercise Price :	  	US                    
		
	Type of Option:	  	         Incentive Stock Option
		
		  	         Nonstatutory Stock Option
		
	Term/Expiration Date:	  	Ten Year Anniversary of Date of Grant

 Vesting Schedule: 

This Option shall be exercisable, in whole or in part, according to the following vesting schedule: 

 

	 	•	 	Ten percent (10%) of the shares subject to the Option shall vest on the first anniversary of the Vesting Commencement Date, then 

 

	 	•	 	Twenty percent (20%) of the shares subject to the Option shall vest 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 the Option shall vest 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 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 the Option shall vest 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 forth 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. 

Termination Period: 
 This
Option shall be exercisable for three (3) months after Participant ceases to be a Service Provider, unless such termination is due to Participant’s death or Disability, in which case this Option shall be exercisable for twelve
(12) months after Participant ceases to be a Service Provider. Notwithstanding the foregoing sentence, in no event may this Option be exercised after the Term/Expiration Date as provided above and this Option may be subject to earlier
termination as provided in Section 11(c) of the Plan. 
 Further, notwithstanding any terms or conditions of the Plan or this Agreement
to the contrary, in the event of termination of Participant’s relationship as a Service Provider, Participant’s right to vest in the Option under the Plan, if any, will terminate effective as of the date that Participant is no longer
actively providing service to the Company or a Subsidiary or Parent of the Company and will not be extended by any notice period mandated under local law (e.g., Participant’s active relationship as a Service Provider would not include a period
of “garden leave” or similar period pursuant to local law); furthermore, in the event of termination of Participant’s relationship as a Service Provider (whether or not in breach of local labor laws), Participant’s right to
receive Shares pursuant to the Option after such termination, if any, will be measured by the date of termination of Participant’s active Service Provider relationship and will not be extended by any notice period mandated under local law; the
Administrator shall have the exclusive discretion to determine when Participant is no longer in an active Service Provider relationship for purposes of the Option. 

II. AGREEMENT 
 1. Grant of
Option. The Administrator of the Company hereby grants to the Participant named in the Notice of Stock Option Grant in Part I of this Agreement (“Participant”), an option (the “Option”) to purchase the number of Shares set
forth in the Notice of Stock Option Grant, at the exercise price per Share set forth in the Notice of Stock Option Grant (the “Exercise Price”), and subject to the terms and conditions of the Plan, which is incorporated herein by
reference. Subject to Section 19(c) of the Plan, in the event of a conflict between the terms and conditions of the Plan and this Option Agreement, the terms and conditions of the Plan shall prevail. 

  
 -2- 

 If designated in the Notice of Stock Option Grant as an Incentive Stock Option (“ISO”),
this Option is intended to qualify as an Incentive Stock Option as defined in Section 422 of the Code. Nevertheless, to the extent that it exceeds the $100,000 rule of Code Section 422(d), this Option shall be treated as a Nonstatutory
Stock Option (“NSO”). Further, if for any reason this Option (or portion thereof) shall not qualify as an ISO, then, to the extent of such nonqualification, such Option (or portion thereof) shall be regarded as a NSO granted under the
Plan. In no event shall the Administrator, the Company or any Parent or Subsidiary or any of their respective employees or directors have any liability to Participant (or any other person) due to the failure of the Option to qualify for any reason
as an ISO. 
 2. Exercise of Option. 

(a) Right to Exercise. This Option shall be exercisable during its term in accordance with the Vesting Schedule set out in the Notice of
Stock Option Grant and with the applicable provisions of the Plan and this Option Agreement. 
 (b) Method of Exercise. This Option
shall be exercisable by delivery of an exercise notice in the form attached as Exhibit A (the “Exercise Notice”) or in a manner and pursuant to such procedures as the Administrator may determine, which shall state the election
to exercise the Option, the number of Shares with respect to which the Option is being exercised, and such other representations and agreements as may be required by the Company. The Exercise Notice shall be accompanied by payment of the aggregate
Exercise Price as to all Exercised Shares, together with any applicable tax withholding. This Option shall be deemed to be exercised upon receipt by the Company of such fully executed Exercise Notice accompanied by the aggregate Exercise Price,
together with any applicable tax withholding. 
 No Shares shall be issued pursuant to the exercise of an Option unless such issuance and
such exercise comply with Applicable Laws. Assuming such compliance, for income tax purposes the Shares shall be considered transferred to Participant on the date on which the Option is exercised with respect to such Shares. 

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 Option is exercised, Participant shall, if required by the Company, concurrently with the exercise of all or any portion of this Option, deliver to the Company his or her Investment Representation Statement in the form attached
hereto as Exhibit B. 
 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 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). 

  
 -3- 

 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 Option or shares acquired pursuant to the Option
shall be bound by this Section 4. 
 5. Method of Payment. Payment of the aggregate Exercise Price shall be by any of the
following, or a combination thereof, at the election of the Participant: 
 (a) cash; 

(b) check; 
 (c) consideration
received by the Company under a formal cashless exercise program adopted by the Company in connection with the Plan; or 
 (d) surrender of
other Shares which (i) shall be valued at its Fair Market Value on the date of exercise, and (ii) must be owned free and clear of any liens, claims, encumbrances or security interests, if accepting such Shares, in the sole discretion of
the Administrator, shall not result in any adverse accounting consequences to the Company. 
 6. Restrictions on Exercise. This
Option may not be exercised until such time as the Plan has been approved by the stockholders of the Company, or if the issuance of such Shares upon such exercise or the method of payment of consideration for such shares would constitute a violation
of any Applicable Law. 
 7. Non-Transferability of Option. This Option 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 Option Agreement shall be binding upon the executors, administrators, heirs, successors and assigns
of Participant. 

  
 -4- 

 8. Term of Option. This Option may be exercised only within the term set out in the Notice
of Stock Option Grant, and may be exercised during such term only in accordance with the Plan and the terms of this Option. 
 9. Tax
Obligations. 
 (a) Tax Withholding. Participant agrees to make appropriate arrangements with the Company (or the Parent or
Subsidiary employing or retaining Participant) for the satisfaction of all Federal, state, local and foreign income and employment tax withholding requirements applicable to the Option exercise. 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 exercise. 

(b) Notice of Disqualifying Disposition of ISO Shares. If the Option granted to Participant herein is an ISO, and if Participant sells
or otherwise disposes of any of the Shares acquired pursuant to the ISO on or before the later of (i) the date two (2) years after the Date of Grant, or (ii) the date one (1) year after the date of exercise, Participant shall
immediately notify the Company in writing of such disposition. Participant agrees that Participant may be subject to income tax withholding by the Company on the compensation income recognized by Participant. 

(c) Code Section 409A. To the extent any Participant is subject to U.S. federal income taxation, the following provision applies.
Under Code Section 409A, an Option that vests after December 31, 2004 (or that vested on or prior to such date but which was materially modified after October 3, 2004) that was granted with a per Share exercise price that is
determined by the Internal Revenue Service (the “IRS”) to be less than the Fair Market Value of a Share on the date of grant (a “discount option”) may be considered “deferred compensation.” An Option that is a
“discount option” may result in (i) income recognition by Participant prior to the exercise of the Option, (ii) an additional twenty percent (20%) federal income tax, and (iii) potential penalty and interest charges.
The “discount option” may also result in additional state income, penalty and interest tax to the Participant. Participant acknowledges that the Company cannot and has not guaranteed that the IRS will agree that the per Share exercise
price of this Option equals or exceeds the Fair Market Value of a Share on the date of grant in a later examination. Participant agrees that if the IRS determines that the Option was granted with a per Share exercise price that was less than the
Fair Market Value of a Share on the date of grant, Participant shall be solely responsible for Participant’s costs related to such a determination. 

10. Entire Agreement; Governing Law. The Plan is incorporated herein by reference. The Plan and this Option Agreement 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. This Agreement is governed by the internal substantive laws but not the choice of law rules of Delaware. 

  
 -5- 

 11. No Guarantee of Continued Service. PARTICIPANT ACKNOWLEDGES AND AGREES THAT THE
VESTING OF SHARES 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, BEING
GRANTED THIS OPTION OR ACQUIRING 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. 
 12.
Acknowledgements; Nature of Option. By entering into this Agreement and accepting the grant of an Option evidenced hereby, Participant acknowledges that: 

(a) the grant of the Option is voluntary and occasional and does not create any contractual or other right to receive future grants of Options,
or benefits in lieu of Options, even if Options have been granted repeatedly in the past; 
 (b) all decisions with respect to future Option
grants, if any, will be at the sole discretion of the Administrator; 
 (c) Participant is voluntarily participating in the Plan; 

(d) the Option is an extraordinary item which does not constitute compensation of any kind for services of any kind rendered to the Company or
the Parent or Subsidiary retaining Participant and which is outside the scope of Participant’s employment contract, if any; 
 (e) the
Option is not part of normal or expected compensation or salary for any purpose, including, but not limited to, calculating any severance, resignation, termination, redundancy, end-of-service payments, bonuses, long-service awards, pension or
retirement benefits or similar payments; 
 (f) in the event that the Parent or Subsidiary retaining Participant, is not the Company, the
grant of an Option will not be interpreted to form an employment contract or relationship with the Company; and furthermore, the Option grant will not be interpreted to form an employment contract with the Company or any Parent or Subsidiary of the
Company; 
 (g) the future value of the underlying Shares is unknown and cannot be predicted with certainty; 

(h) if the underlying Shares do not increase in value, the Option will have no value; 

(i) if Participant exercises the Option and obtains Shares, the value of those Shares acquired upon exercise may increase or decrease in value,
even below the Exercise Price; 

  
 -6- 

 (j) in consideration of the grant of the Option, no claim or entitlement to compensation or
damages arises from termination of the Option or diminution in value of the Option or Shares purchased through exercise of the Option resulting from termination of Participant’s Service Provider relationship by the Company or by the Parent or
Subsidiary retaining Participant (for any reason whether or not in breach of applicable labor laws) and Participant irrevocably releases the Company or the Parent or Subsidiary retaining Participant from any such claim that may arise; if,
notwithstanding the foregoing, any such claim is found by a court of competent jurisdiction to have arisen then, by signing this Agreement, Participant shall be deemed irrevocably to have waived his or her entitlement to pursue such a claim; 

(k) it is Participant’s sole responsibility to investigate and comply with any applicable exchange control laws in connection with the
issuance and delivery of Shares pursuant to the exercise of the Option; 
 (l) the Company or the Parent or Subsidiary retaining Participant
are not providing any tax, legal or financial advice, nor are the Company or the Parent or Subsidiary retaining Participant making any recommendations regarding Participant’s participation in the Plan or Participant’s acquisition or sale
of the Shares underlying the Option; and 
 (m) Participant is hereby advised to consult with his or her own personal tax, legal and
financial advisors regarding his or her participation in the Plan before taking any action related to the Plan. 
 13. Data Privacy.
By entering into this Option Agreement, and as a condition of the grant of the Option, Participant hereby explicitly and unambiguously consents to the collection, use and transfer, in electronic or other form, of Participant’s personal data as
described in this document by and among, as applicable, the Company and any Parent or Subsidiary of the Company for the exclusive purpose of implementing, administering and managing Participant’s participation in the Plan. 

Participant understands that the Company and any Parent or Subsidiary of the Company hold certain personal information about Participant,
including, but not limited to, Participant’s name, home address and telephone number, date of birth, social insurance number or other identification number, salary, nationality, job title, any Shares or directorships held in the Company,
details of all Options or any other entitlement to Shares awarded, canceled, exercised, vested, unvested or outstanding in Participant’s favor, as the Parent or Subsidiary retaining Participant and/or the Company deems necessary for the purpose
of implementing, administering and managing the Plan (“Data”). Participant acknowledges and understands that Data may be transferred to any broker as designated by the Company and any third parties assisting in the implementation,
administration and management of the Plan, that these recipients may be located in Participant’s country or applicable area, and that the recipient’s country may have different data privacy laws and protections than Participant’s
country. Participant understands that he or she may request a list with the names and addresses of any potential recipients of the Data by contacting Participant’s local human resources representative. Participant authorizes the recipients to
receive, possess, use, retain and transfer the Data, in electronic or other form, for the purposes of implementing, administering and managing Participant’s participation in the Plan, including any requisite transfer of such Data as may be
required to a broker or other 

  
 -7- 

 
third party with whom Participant may elect to deposit any Shares acquired upon exercise of the Option. Participant understands that Data will be held only as long as is necessary to implement,
administer and manage his or her participation in the Plan. Participant understands that he or she may, at any time, view Data, request additional information about the storage and processing of Data, require any necessary amendments to Data or
refuse or withdraw the consents herein, in any case without cost, by contacting in writing his or her local human resources representative. Participant understands, however, that refusing or withdrawing his or her consent may affect his or her
ability to exercise or realize benefits from the Option or otherwise participate in the Plan. For more information on the consequences of his or her refusal to consent or withdrawal of consent, Participant understands that he or she may contact his
or her local human resources representative. 
 14. Language. If Participant has received this Agreement or any other document
related to the Plan translated into a language other than English and if the translated version is different than the English version, the English version will control unless otherwise prescribed by local law. 

15. Consent to Receive Information in English. The parties acknowledge that it is their express wish that this agreement, as well as
all documents, notices and legal proceeds entered into, given or instituted pursuant hereto or relating directly or indirectly hereto, be drawn up in English. 

Les parties reconnaissent avoir exigé la rédaction en anglais de cette convention, ainsi que de tous documents
exécutés, avis donnés et procédures judiciaries intentées, directement ou indirectement, relativement à ou suite à la présente convention. 

[Remainder of page intentionally left blank] 

  
 -8- 

 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 Option subject to all of the terms and provisions thereof. Participant has reviewed the Plan and this Option in their entirety, has had an opportunity to obtain the advice of counsel
prior to executing this Option and fully understands all provisions of the Option. 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 Option. Participant further agrees to notify the Company upon any change in the residence address indicated below. 
  

					
	PARTICIPANT	 		 	UPLAND SOFTWARE, INC.
			
	 	 		 	  

	Signature	 		 	By
			
	 	 		 	  

	Print Name	 		 	Print Name
			
	 	 		 	  

		 		 	Title
			
	 	 		 	
	Residence Address	 		 	

  
 -9- 

 EXHIBIT A 

2010 STOCK PLAN 

EXERCISE NOTICE 
 Upland Software, Inc.

 401 Congress Ave., Suite 2950 
 Austin, Texas 78701 

Attention: Chief Financial Officer 
 1.
Exercise of Option. Effective as of today,             ,     , the undersigned (“Participant”) hereby elects to exercise
Participant’s option (the “Option”) to purchase              shares of the Common Stock (the “Shares”) of Upland Software, Inc. (the “Company”)
under and pursuant to the 2010 Stock Plan (the “Plan”) and the Stock Option Agreement dated             (the “Option Agreement”). 

2. Delivery of Payment. Participant herewith delivers to the Company the full purchase price of the Shares, as set forth in the Option
Agreement, and any and all withholding taxes due in connection with the exercise of the Option. 
 3. Representations of Participant.
Participant acknowledges that Participant has received, read and understood the Plan and the Option Agreement and agrees to abide by and be bound by their terms and conditions. 

4. Rights as Stockholder. Until the issuance of the Shares (as evidenced by the appropriate entry on the books of the Company or of a
duly authorized transfer agent of the Company), no right to vote or receive dividends or any other rights as a stockholder shall exist with respect to the Common Stock subject to an Award, notwithstanding the exercise of the Option. The Shares shall
be issued to Participant as soon as practicable after the Option is exercised in accordance with the Option Agreement. No adjustment shall be made for a dividend or other right for which the record date is prior to the date of issuance except as
provided in Section 11 of the Plan. 
 5. Company’s Right of First Refusal. 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 5 (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). 

 (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 (“Purchase
Price”) for the Shares purchased by the Company or its assignee(s) under this Section 5 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 of Directors of the Company in good faith. 
 (d) Payment. Payment of the Purchase 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 5, 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 5 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 5 notwithstanding, the transfer of any or all of the Shares during the Participant’s lifetime or on the Participant’s death by will or intestacy to the Participant’s immediate
family or a trust for the benefit of the Participant’s immediate family shall be exempt from the provisions of this Section 5. “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 Section 5, and there shall be no further transfer of such Shares except in accordance with the
terms of this Section 5. 
 (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. 

  
 -2- 

 6. Tax Consultation. Participant understands that Participant may suffer adverse tax
consequences as a result of Participant’s purchase or disposition of the Shares. Participant represents that Participant has consulted with any tax consultants Participant deems advisable in connection with the purchase or disposition of the
Shares and that Participant is not relying on the Company for any tax advice. 
 7. 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 COMPANY 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 AND A RIGHT OF FIRST REFUSAL HELD BY
THE ISSUER OR ITS ASSIGNEE(S) AS SET FORTH IN THE EXERCISE NOTICE 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 AND RIGHT OF FIRST
REFUSAL 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 Exercise Notice 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. 

  
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 8. Successors and Assigns. The Company may assign any of its rights under this Exercise
Notice to single or multiple assignees, and this Exercise Notice shall inure to the benefit of the successors and assigns of the Company. Subject to the restrictions on transfer herein set forth, this Exercise Notice shall be binding upon
Participant and his or her heirs, executors, administrators, successors and assigns. 
 9. Interpretation. Any dispute regarding the
interpretation of this Exercise Notice 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. 
 10. Governing Law; Severability. This Exercise Notice is governed by the internal substantive
laws, but not the choice of law rules, of Delaware. In the event that any provision hereof becomes or is declared by a court of competent jurisdiction to be illegal, unenforceable or void, this Exercise Notice shall continue in full force and
effect. 
 11. Entire Agreement. The Plan and Option Agreement are incorporated herein by reference. This Exercise Notice, the Plan,
the Option Agreement and the Investment Representation Statement 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. 

 

					
	Submitted by:	 		 	Accepted by:
	PARTICIPANT	 		 	UPLAND SOFTWARE, INC.
			
	 	 		 	  

	Signature	 		 	By
			
	 	 		 	  

	Print Name	 		 	Print Name
			
		 		 	  

		 		 	Title
			
	Address:	 		 	Address:
			
	 	 		 	401 Congress Ave., Suite 2950
	 	 		 	Austin, TX 78701
			
		 		 	  

		 		 	Date Received

  
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 EXHIBIT B 

INVESTMENT REPRESENTATION STATEMENT 
  

					
	PARTICIPANT	  	:	  	
			
	COMPANY	  	:	  	UPLAND SOFTWARE, INC.
			
	SECURITY	  	:	  	COMMON STOCK
			
	AMOUNT	  	:	  	                         SHARES
			
	DATE	  	:	  	                        

 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 (1) 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 Option 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 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 Option, 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
		
		 	 
		 	Signature
		
		 	 
		 	Print Name
		
		 	 
		 	Date

  
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