EX-10.4.2



 Exhibit 10.4.2 

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. 

Notwithstanding the foregoing, in the event that Participant is terminated without Cause or leaves for Good Reason within nine months
following a Change in Control (as defined in the Plan), the vesting of the Option shall accelerate as to that number of shares of Common Stock of the Company that would have vested had Participant remained an employee for two additional years. 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 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 

  
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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. 

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. 

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


  
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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). 

  
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 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. 
 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. 

  
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 (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. 

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 

  
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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; 
 (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 

  
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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 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


  
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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] 

  
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 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	 		 	


  
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 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. 

  
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 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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