0001193125-14-332241 Sample Contracts

SECURITY AGREEMENT (TENROX US)
Security Agreement • September 4th, 2014 • Upland Software, Inc. • Services-prepackaged software • California

This Security Agreement (this “Agreement”) is made and entered into as of March 5, 2012 (“Closing Date”) by and between the undersigned (“Grantor”), and COMERICA BANK (the “Bank”).

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SILVERBACK ACQUISITION CORPORATION RESTRICTED STOCK PURCHASE AGREEMENT
Restricted Stock Purchase Agreement • September 4th, 2014 • Upland Software, Inc. • Services-prepackaged software • Texas

This Restricted Stock Purchase Agreement (the “Agreement”) is made as of October 18, 2010 by and between Silverback Acquisition Corporation, a Delaware corporation (the “Company”), and John T. McDonald (the “Purchaser”).

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UPLAND SOFTWARE, INC.
Restricted Stock Purchase Agreement • September 4th, 2014 • Upland Software, Inc. • Services-prepackaged software • Texas

Unless otherwise defined herein, the terms defined in the 2010 Stock Plan, as amended (the “Plan”) shall have the same defined meanings in this Restricted Stock Purchase Agreement (the “Agreement”).

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UNCONDITIONAL GUARANTY (Marex Group)
Upland Software, Inc. • September 4th, 2014 • Services-prepackaged software • California

For and in consideration of the loan by COMERICA BANK (“Bank”) to TENROX INC. (“Borrower”), which loan is made pursuant to a Loan and Security Agreement between Borrower and Bank dated as of May 16, 2013, as amended from time to time (the “Agreement”), and acknowledging that Bank would not enter into the Agreement without the benefit of this Guaranty (this “Guaranty”), the undersigned guarantor (“Guarantor”) hereby unconditionally and irrevocably guarantees the prompt and complete payment of all amounts that Borrower owes to Bank and performance by Borrower of the Agreement and any other agreements between Borrower and Bank, as amended from time to time (collectively referred to as the “Agreements”), in strict accordance with their respective terms. Notwithstanding anything to the contrary in this Guaranty, the obligations of Borrower to the Bank covered by this Guaranty shall not include any obligation of a Borrower to Bank with respect to a “swap,” as defined in Section 1(a)(47) of t

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UPLAND SOFTWARE, INC.
Stock Option Agreement • September 4th, 2014 • Upland Software, Inc. • Services-prepackaged software • Delaware

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”).

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Contract
Upland Software, Inc. • September 4th, 2014 • Services-prepackaged software • California

THIS WARRANT AND THE SHARES ISSUABLE HEREUNDER HAVE NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE “ACT”), OR ANY APPLICABLE STATE SECURITIES LAWS, AND, EXCEPT AND PURSUANT TO THE PROVISIONS OF ARTICLE 5 BELOW, MAY NOT BE OFFERED, SOLD OR OTHERWISE TRANSFERRED WITHOUT AN EFFECTIVE REGISTRATION THEREOF UNDER THE ACT AND ANY APPLICABLE STATE SECURITIES LAWS, OR PURSUANT TO RULE 144 OR AN EXEMPTION FROM THE REGISTRATION REQUIREMENTS OF THE ACT AND ANY APPLICABLE STATE SECURITIES LAWS. THE SHARES ISSUABLE HEREUNDER ARE SUBJECT TO A LOCK-UP PERIOD AFTER THE EFFECTIVE DATE OF THE ISSUER’S REGISTRATION STATEMENT FILED UNDER THE ACT, AS SET FORTH IN AN AGREEMENT BETWEEN THE COMPANY AND THE ORIGINAL HOLDER OF THESE SECURITIES, A COPY OF WHICH MAY BE OBTAINED AT THE ISSUER’S PRINCIPAL OFFICE, SUCH LOCK-UP PERIOD IS BINDING ON TRANSFEREES OF THE SHARES.

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SILVERBACK TWO CANADA MERGER CORPORATION LOAN AND SECURITY AGREEMENT
Loan and Security Agreement • September 4th, 2014 • Upland Software, Inc. • Services-prepackaged software • California

This LOAN AND SECURITY AGREEMENT (this “Agreement”) is entered into as of February 10, 2012, by and between Comerica Bank (“Bank”) and Silverback Two Canada Merger Corporation (“Borrower”).

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UPLAND SOFTWARE, INC. AMENDMENT TO STOCK OPTION AGREEMENT
Stock Option Agreement • September 4th, 2014 • Upland Software, Inc. • Services-prepackaged software • Texas

This Amendment to Stock Option 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 Stock Option Agreement previously entered into between the Company and the Participant with respect to the Option (as defined below) (the “Stock Option Agreement”).

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STOCK PURCHASE AGREEMENT dated as of December 23, 2013 by and among UPLAND SOFTWARE, INC., CLICKABILITY, INC. and LIMELIGHT NETWORKS, INC. relating to the purchase and sale of 100% of the outstanding shares of capital stock of CLICKABILITY, INC.
Stock Purchase Agreement • September 4th, 2014 • Upland Software, Inc. • Services-prepackaged software • Delaware

This STOCK PURCHASE AGREEMENT (this “Agreement”), dated as of December 23, 2013, is entered into by and among Upland Software, Inc., a Delaware corporation (“Buyer”), Clickability, Inc., a Delaware corporation formerly known as Limelight Web Content Management, Inc. (the “Company”), and Limelight Networks, Inc., a Delaware corporation (the “Seller”). The Company, the Seller and Buyer are collectively referred to herein as the “Parties” and each individually as a “Party.”

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MEMBERSHIP INTEREST PURCHASE AGREEMENT BY AND AMONG SILVERBACK ENTERPRISE GROUP, INC., UPLAND SOFTWARE, INC., COMSCI, LLC, AND ROBERT J. SVEC and ALAN C. MALTZ, as SELLING MEMBERS, Dated as of November 7, 2013
Membership Interest Purchase Agreement • September 4th, 2014 • Upland Software, Inc. • Services-prepackaged software • Delaware

THIS MEMBERSHIP INTEREST PURCHASE AGREEMENT (this “Agreement”) is made and entered into as of November 7, 2013 by and among Silverback Enterprise Group, Inc., a Delaware corporation (“Parent”), Upland Software, Inc., a Delaware corporation and wholly owned subsidiary of Parent (“Purchaser”), ComSci, LLC, a New Jersey limited liability company (the “Company”), and Robert J. Svec and Alan C. Maltz, the members of the Company (each a “Selling Member” and collectively, the “Selling Members”). Capitalized terms not otherwise defined herein shall have the meaning set forth on Annex A hereto.

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LEASE AGREEMENT
Lease Agreement • September 4th, 2014 • Upland Software, Inc. • Services-prepackaged software

This Lease Agreement (“Lease”) is entered into as of February 27th, 2014 (the “Effective Date”), by and between TPG- 401 Congress LLC, a Delaware limited liability company (“Landlord”), and Upland Software, Inc., a Delaware corporation (“Tenant”). In consideration of the mutual covenants set forth herein, Landlord and Tenant agree as follows:

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LOAN AND SECURITY AGREEMENT SILVERBACK ENTERPRISE GROUP, INC. VISIONAEL CORPORATION and POWERSTEERING SOFTWARE, INC.
Loan and Security Agreement • September 4th, 2014 • Upland Software, Inc. • Services-prepackaged software • California

This LOAN AND SECURITY AGREEMENT (this “Agreement”) is entered into as of March 5, 2012, among Comerica Bank (“Bank”), Silverback Enterprise Group, Inc., a Delaware corporation (“Silverback”), Visionael Corporation, a Delaware corporation (“Visionael”) and PowerSteering Software, Inc., a Delaware corporation (“PowerSteering” and collectively with Silverback and Visionael, the “Borrowers” and each individually a “Borrower”).

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PLEDGE AND SECURITY AGREEMENT (Silverback Enterprise)
Pledge and Security Agreement • September 4th, 2014 • Upland Software, Inc. • Services-prepackaged software • California

This Pledge and Security Agreement (this “Agreement”) is made and entered into as of February 10, 2012 (“Closing Date”) by and between the undersigned (“Grantor”), and COMERICA BANK (the “Bank”).

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MANAGEMENT RIGHTS AGREEMENT
Management Rights Agreement • September 4th, 2014 • Upland Software, Inc. • Services-prepackaged software

THIS MANAGEMENT RIGHTS AGREEMENT (this “Agreement”) is entered into as of October 28, 2010 by and between Silverback Acquisition Corporation, a Delaware corporation (the “Company”), and Austin Ventures X, L.P., a Delaware limited partnership (the “Fund”) (together, the “Parties”).

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UPLAND SOFTWARE, INC. EXECUTIVE EMPLOYMENT AGREEMENT
Executive Employment Agreement • September 4th, 2014 • Upland Software, Inc. • Services-prepackaged software • Texas

This Executive Employment Agreement (the “Agreement”) is entered into as of July 25, 2014 (the “Effective Date”) by and between Upland Software, Inc., a Delaware corporation (the “Company”), and R. Brian Henley (“Executive”).

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UPLAND SOFTWARE, INC. STOCK PURCHASE AGREEMENT
Stock Purchase Agreement • September 4th, 2014 • Upland Software, Inc. • Services-prepackaged software • Texas

This Stock Purchase Agreement (the “Agreement”) is made as of January 27, 2014, by and between Upland Software, Inc., a Delaware corporation (the “Company”), and DevFactory FZ-LLC (the “Purchaser”).

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UPLAND SOFTWARE, INC. AMENDED AND RESTATED INVESTORS’ RIGHTS AGREEMENT December 20, 2013
Investors’ Rights Agreement • September 4th, 2014 • Upland Software, Inc. • Services-prepackaged software • Delaware

This Amended and Restated Investors’ Rights Agreement (this “Agreement”) is dated as of December 20, 2013, and is between Upland Software, Inc. (f/k/a Silverback Enterprise Group, Inc.), a Delaware corporation (the “Company”), and the persons and entities listed on Exhibit A (each, an “Investor” and collectively, the “Investors”).

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January 1, 2014 DevFactory FZ-LLC Seventh Floor Dubai Media City UNITED ARAB EMIRATES Re: Letter Agreement Regarding Amended and Restated Technology Services Agreement (“Letter Agreement”)
Technology Services Agreement • September 4th, 2014 • Upland Software, Inc. • Services-prepackaged software • Texas

Reference is made to that certain Technology Services Agreement, dated as of January 19, 2012, and amended by that certain Amendment #1 dated as of January 26, 2012 (as amended, the “Original Services Agreement”), by and between Upland Software, Inc. (the “Upland”) and DevFactory FZ- LLC (the “DevFactory”), which was further amended and restated in its entirety by that certain Amended and Restated Technology Services Agreement (the “Restated Services Agreement”), dated as of the date hereof, by and between Upland and DevFactory. Capitalized terms used but not defined herein shall have the meanings ascribed to them in the Restated Services Agreement. Upland and DevFactory agree as follows:

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UNCONDITIONAL GUARANTY (PowerSteering)
Unconditional Guaranty • September 4th, 2014 • Upland Software, Inc. • Services-prepackaged software • California

For and in consideration of the loan by COMERICA BANK (“Bank”) to SILVERBACK TWO CANADA MERGER CORPORATION (“Borrower”), which loan is made pursuant to a Loan and Security Agreement between Borrower and Bank dated as of February 10, 2012, as amended from time to time (the “Agreement”), and acknowledging that Bank would not enter into the Agreement without the benefit of this Guaranty (this “Guaranty”), the undersigned guarantor (“Guarantor”) hereby unconditionally and irrevocably guarantees the prompt and complete payment of all amounts that Borrower owes to Bank and performance by Borrower of the Agreement and any other agreements between Borrower and Bank, as amended from time to time (collectively referred to as the “Agreements”), in strict accordance with their respective terms.

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UPLAND SOFTWARE, INC.
Stock Option Agreement • September 4th, 2014 • Upland Software, Inc. • Services-prepackaged software • Delaware

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”).

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LEASE AGREEMENT
Lease Agreement • September 4th, 2014 • Upland Software, Inc. • Services-prepackaged software • Quebec

THIS LEASE AGREEMENT is made as of this 5th day of November, 2012, between A.R.E. QUEBEC NO. 2, INC., a company incorporated under the Companies Act (Quebec) (“Landlord”), and TENROX INC., a corporation organized under the Canada Business Corporations Act, doing business as Power Steering Software (“Tenant”).

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SUBLEASE AGREEMENT
Sublease Agreement • September 4th, 2014 • Upland Software, Inc. • Services-prepackaged software • Nebraska

THIS SUBLEASE AGREEMENT (this “Sublease”), dated effective as of the 10th day of May, 2013 (the “Effective Date”), is entered into by and between MAREX PROPERTIES, LLC, a Nebraska limited liability company (“Sublessor”), and MAREX GROUP, INC., a Nebraska corporation (“Sublessee”).

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AGREEMENT AND PLAN OF MERGER by and among SILVERBACK ENTERPRISE GROUP, INC., STEERING WHEEL ACQUISITION CORP., POWERSTEERING SOFTWARE, INC. and MICHAEL PEHL, as STOCKHOLDER REPRESENTATIVE February 3, 2012
Agreement and Plan of Merger • September 4th, 2014 • Upland Software, Inc. • Services-prepackaged software • Delaware

THIS AGREEMENT AND PLAN OF MERGER (the “Agreement”) is made and entered into as of February 3, 2012, by and among Silverback Enterprise Group, Inc., a Delaware corporation (“Buyer”), Steering Wheel Acquisition Corp., a Delaware corporation and wholly-owned subsidiary of Buyer (“Acquisition Corp”), PowerSteering Software, Inc., a Delaware corporation (the “Company”), and Michael Pehl (the “Stockholder Representative”).

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STOCK PURCHASE AGREEMENT BY AND AMONG SILVERBACK ENTERPRISE GROUP, INC., MAREX GROUP, INC., FILEBOUND SOLUTIONS, INC., SELLING STOCKHOLDERS, AND REX LAMB, AS THE STOCKHOLDER REPRESENTATIVE, Dated as of May 16, 2013
Stock Purchase Agreement • September 4th, 2014 • Upland Software, Inc. • Services-prepackaged software • Delaware

THIS STOCK PURCHASE AGREEMENT (this “Agreement”) is made and entered into as of May 16, 2013 by and among Silverback Enterprise Group, Inc., a Delaware corporation (“Purchaser”), Marex Group, Inc., a Nebraska corporation, FileBound Solutions, Inc., a Florida corporation (each, a “Company” and collectively the “Companies”), the stockholders of the Companies (each a “Selling Stockholder” and collectively, the “Selling Stockholders”) and Rex Lamb, as the exclusive representative of the Selling Stockholders in connection with the transactions contemplated by this Agreement (the “Stockholder Representative”), solely in his capacity as the Stockholder Representative hereunder for purposes of Sections 1.3, 1.7, 5.5 and 5.17 and Article 7 hereof. Capitalized terms not otherwise defined herein shall have the meaning set forth on Annex A hereto.

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FIRST AMENDMENT
First Amendment • September 4th, 2014 • Upland Software, Inc. • Services-prepackaged software

THIS FIRST AMENDMENT (this “Amendment”) is made and entered into as of , 2014 (the “Effective Date”), by and between PKY-401 CONGRESS, LLC, a Delaware limited liability company (“Landlord”), and UPLAND SOFTWARE, INC., a Delaware corporation (“Tenant”).

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UNCONDITIONAL GUARANTY (TENROX US)
Upland Software, Inc. • September 4th, 2014 • Services-prepackaged software • California

For and in consideration of the loan by COMERICA BANK (“Bank”) to VISIONAEL CORPORATION, a Delaware corporation, SILVERBACK ENTERPRISE GROUP, INC., a Delaware corporation and POWERSTEERING SOFTWARE, INC., a Delaware corporation (each a “Borrower” and collectively, “Borrowers”), which loan is made pursuant to a Loan and Security Agreement among Borrowers and Bank dated as of March 5, 2012, as amended from time to time (the “Agreement”), and acknowledging that Bank would not enter into the Agreement without the benefit of this Guaranty (this “Guaranty”), the undersigned guarantor (“Guarantor”) hereby unconditionally and irrevocably guarantees the prompt and complete payment of all amounts that Borrowers, or any of them, owe to Bank and performance by each Borrower of the Agreement and any other agreements between Borrowers, or any of them, and Bank, as amended from time to time (collectively referred to as the “Agreements”), in strict accordance with their respective terms.

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UPLAND SOFTWARE, INC. AMENDMENT TO RESTRICTED STOCK PURCHASE AGREEMENT
Restricted Stock Purchase Agreement • September 4th, 2014 • Upland Software, Inc. • Services-prepackaged software • Texas

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”).

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