Document:

EX-10.5.1

 Exhibit 10.5.1 

UPLAND SOFTWARE, INC. 

2010 STOCK PLAN 

AMENDMENT TO RESTRICTED STOCK PURCHASE AGREEMENT 

This Amendment to Restricted Stock Purchase Agreement (this “Amendment”) is made effective as of
            , 2014 (the “Amendment Date”) by and between Upland Software, Inc., a Delaware corporation (the “Company”), and
            (the “Participant”). Capitalized terms used but not defined herein shall have the respective meanings assigned to them in the Upland Software, Inc. 2010
Stock Plan, as amended (the “Plan”) or the Restricted Stock Purchase Agreement previously entered into between the Company and the Participant with respect to the Shares (as defined below) (the “Stock
Agreement”). 
 RECITALS 

WHEREAS: The Company sold and issued to the Participant             shares
of Common Stock at a price of $            per share (the “Shares”); 

WHEREAS: On September 2, 2014 the Company’s Board of Directors approved an amendment to the Stock Agreement to revise the
vesting schedule to include certain vesting acceleration provisions; 
 WHEREAS: In connection with the foregoing, and to give effect
to such amendment to the Stock Agreement, the Stock Agreement is amended as set forth herein. 
 AGREEMENT 

NOW, THEREFORE: The parties agree as follows: 

1. Amendment of Stock Agreement. The Stock Agreement is hereby amended as follows: 

a. Amendment of Vesting Schedule. The Vesting Schedule as set forth in Section I (Notice of Grant of Restricted Stock) of the Stock
Agreement is hereby amended and restated in its entirety as follows: 
 Vesting Schedule: 

Twenty-five percent (25%) of the total number of Shares shall be released from the Repurchase Option on the one-year anniversary of the
Vesting Commencement Date, and the remaining seventy-five (75%) of the total number of Shares shall be released from the Repurchase Option in equal monthly installments thereafter over thirty-six (36) months on the corresponding day of
each relevant month (or if there is no corresponding day in any such month, on the last day of such month), subject to Participant continuing to be a Service Provider through each such date. 

 Any of the Shares which have not yet been released from the Company’s Repurchase Option are
referred to herein as “Unreleased Shares.” The Shares which have been released from the Company’s Repurchase Option shall be delivered to Participant at Participant’s request (see Section 11 of Part II of this Agreement).

 Notwithstanding the foregoing, in the event that Participant is terminated without Cause or leaves for Good Reason within twelve months
following a Change in Control (as defined in the Plan), then one hundred percent (100%) of the shares subject to the Repurchase Option shall accelerate as of immediately prior to such termination. For the purposes of this Agreement,
“Cause” means (i) Participant’s willful or grossly negligent failure to substantially perform the duties and obligations of Participant’s position with the Company; (ii) any act of personal dishonesty, fraud or
misrepresentation taken by Participant which was intended to result in substantial gain or personal enrichment of Participant at the expense of the Company; (iii) Participant’s violation of a federal or state law or regulation applicable
to the Company’s business which violation was or is reasonably likely to be injurious to the Company; (iv) Participant’s conviction of, or plea of nolo contendere or guilty to, a felony under the laws of the United States or any
State, excluding felonies for minor traffic violation and vicarious liability (so long as Participant did not know of the felony and did not willfully violate the law); (v) Participant’s material breach of the terms of the Proprietary
Information Agreement with the Company. For the purposes of this Agreement, “Good Reason” means (i) without Participant’s consent, a material reduction of Participant’s duties or responsibilities relative to
Participant’s duties or responsibilities as in effect immediately prior to such reduction; provided, however, any reduction in Participant’s duties or responsibilities resulting solely from the Company being acquired by and
made a part of a larger entity (as, for example, when a chief executive officer becomes an employee of the acquiring corporation following a Change in Control but is not the chief executive officer of the acquiring corporation) shall not constitute
Good Reason; (ii) without Participant’s written consent, a material reduction in Participant’s base salary as in effect immediately prior to such reduction, unless such reduction is part of a reduction in expenses generally affecting
senior executives of the Company; (iii) without Participant’s consent, a material reduction by the Company in the kind or level of employee benefits to which Participant was entitled immediately prior to such reduction, with the result
that Participant’s overall benefits package is materially reduced, unless such reduction is part of a reduction in benefits generally affecting senior executives of the Company; or (iv) without Participant’s consent, a relocation to a
facility or a location more than fifty (50) miles from Participant’s then current present working locations. Good Reason shall not exist unless Participant provides (i) notice to the Company within ninety (90) days of the initial
existence of the condition triggering Good Reason and (ii) the Company the opportunity of at least thirty (30) days to cure such condition. A termination from service shall not be considered for Good Reason if such termination occurs later
than two (2) years following the initial existence of the Good Reason condition. Notwithstanding the foregoing, if Participant terminates employment with the Company for Good Reason, but the Company discovers after such termination that
Participant’s conduct during the employment term would have entitled the Company to terminate Participant for Cause, then Participant’s termination shall be for Cause and not for Good Reason and Participant shall remit all amounts paid to
Participant for termination for Good Reason. 

  
 -2- 

 2. Miscellaneous. Except as set forth herein, the Shares and the Stock Agreement shall
continue in full force and effect. This Amendment may be executed in counterparts, each of which shall be an original and all of which together shall constitute one and the same instrument. Notwithstanding the foregoing, this Amendment shall be
effective upon the execution hereof by the Company. This Amendment is governed by the internal substantive laws but not the choice of law rules of the State of Texas. 

* * * * * 

  
 -3- 

 IN WITNESS WHEREOF, the parties have executed this Amendment as of the date first written
above. 
  

			
	UPLAND SOFTWARE, INC.
		
	By:	 	  

	Name:	 	  

	Title:	 	  

  

	
	Acknowledged and agreed:
	
	PARTICIPANT:
	
	  

	
	Address:
	  

	  

	  

	Facsimile #:
                                         
             
	Email:
                                         
                       

 UPLAND SOFTWARE, INC. 

SIGNATURE PAGE TO AMENDMENT TO STOCK
AGREEMENTEX-10.10

 Exhibit 10.10 

SILVERBACK ACQUISITION CORPORATION 

July 23, 2010 
 Mr. John T.
McDonald 

                          
           

                          
           
 Dear Jack: 

I am pleased to offer you a position with Silverback Acquisition Corporation (the “Company”), as its Chairman, Chief Executive
Officer and Treasurer. 
 If you decide to join us, you will not receive any salary until January 2012, other than such minimum wages as may
be required by law. You also will be given the opportunity to purchase 6,558,750 shares of the Company’s Common Stock at a price of $0.0001 per share (the “Shares”), subject to a right of repurchase by the Company (the
“Repurchase Option”), which Repurchase Option shall lapse with respect to one-fourth (1/4) of the Shares on the first anniversary of your employment, with the remaining three-fourths (3/4) of the Shares being released from
the Repurchase Option in equal monthly installments thereafter over thirty-six (36) months subject to the terms of a Restricted Stock Purchase Agreement with the Company (the “Restricted Stock Purchase Agreement”). In the event
that your employment is terminated by the Company without Cause or you voluntarily resign with Good Reason (e.g., relocation or material change in title, duties or salary) (as both such terms are defined in the Restricted Stock Purchase Agreement),
such Shares that would have been released from the Repurchase Option during the 12-month period immediately following the date of such termination shall be immediately released from the Repurchase Option. In the event that your employment is
terminated without Cause or you voluntarily resign with Good Reason following a Change of Control (as defined in the Restricted Stock Purchase Agreement), 100% of the Shares still subject to the Repurchase Option shall be released and no longer be
subject to such Repurchase Option. As an employee, you will also be eligible to receive certain employee benefits upon implementation of such benefit plans and policies by the Company. 

The Company is excited about your joining and looks forward to a beneficial and productive relationship. Nevertheless, you should be aware
that your employment with the Company is for no specified period and constitutes at-will employment. 

 John T. McDonald 

July 23, 2010 
  Page
 2
 
  

 For purposes of federal immigration law, you will be required to provide to the Company
documentary evidence of your identity and eligibility for employment in the United States. Such documentation must be provided to us within three (3) business days of your date of hire, or our employment relationship with you may be terminated.

 We also ask that, if you have not already done so, you disclose to the Company any and all agreements relating to your prior employment
that may affect your eligibility to be employed by the Company or limit the manner in which you may be employed. It is the Company’s understanding that any such agreements will not prevent you from performing the duties of your position and you
represent that such is the case. Moreover, except as listed Schedule A of your Employee Proprietary Information Agreement, you agree that, during the term of your employment with the Company, you will not engage in any other employment,
occupation, consulting or other business activity directly related to the business in which the Company is now involved or becomes involved during the term of your employment, nor will you engage in any other activities that conflict with your
obligations to the Company. Similarly, you agree not to bring any third party confidential information to the Company, including that of your former employer, and that in performing your duties for the Company you will not in any way utilize any
such information. 
 As a condition of your employment, you are also required to sign and comply with an Employee Proprietary Information
Agreement which requires, among other provisions, the assignment of patent rights to any invention made during your employment at the Company, and non-disclosure of Company proprietary information. The
Employee Proprietary Information Agreement will also contain a restriction on your ability to engage in competitive activities for a period of three (3) years from your last date of employment with the Company. 

To accept the Company’s offer, please sign and date this letter in the space provided below. A duplicate original is enclosed for your
records. If you accept our offer, your first day of employment will be July 23, 2010. This letter, along with any agreements relating to proprietary rights between you and the Company, set forth the terms of your employment with the
Company and supersede any prior representations or agreements including, but not limited to, any representations made during your recruitment, interviews or pre-employment negotiations, whether written or
oral. This letter, including, but not limited to, its at-will employment provision, may not be modified or amended except by a written agreement signed by an officer of the Company and you. 

We look forward to your favorable reply and to working with you at Silverback Acquisition Corporation. 

 John T. McDonald 

July 23, 2010 
  Page
 3
 
  

 
	
	Sincerely,
	
	/s/ BRIAN K. BEARD
	Brian K. Beard,
	Secretary

  

			
	Agreed to and accepted:
		
	Signature:	 	/s/ JOHN T. MCDONALD
	Printed Name:	 	John T. McDonald
	Date:	 	7/23/2010

 Enclosures 
 Duplicate Original
Letter 
 Employee Proprietary Information Agreement

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