0001628280-15-002099 Sample Contracts

SECURITY AGREEMENT (Upland IX)
Security Agreement • March 31st, 2015 • Upland Software, Inc. • Services-prepackaged software • California

This Security Agreement (this “Agreement”) is made and entered into as of March 23, 2015 (“Closing Date”) by and between the undersigned (“Grantor”), and COMERICA BANK (the “Bank”).

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UPLAND SOFTWARE, INC.
Restricted Stock Purchase Agreement • March 31st, 2015 • 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”).

UNCONDITIONAL GUARANTY (Upland IX)
Upland Software, Inc. • March 31st, 2015 • Services-prepackaged software • California

For and in consideration of the loan by COMERICA BANK (“Bank”) to UPLAND SOFTWARE, INC. and SOLUTION Q INC. (individually and collectively, the “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. 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

UPLAND SOFTWARE, INC. RESTRICTED STOCK AGREEMENT
Restricted Stock Agreement • March 31st, 2015 • Upland Software, Inc. • Services-prepackaged software • Delaware

, 2014, is entered into by and between Upland Software, Inc., a Delaware corporation (“Company”), and Craig MacInnis (the “Executive”), Karen Smiley-MacInnis (“Karen”), and John David MacInnis (“John” and, together with the Executive and Karen, the “Stockholders” and each a “Stockholder”) (the Stockholders together with the Company, collectively the “Parties” and each, individually, a “Party”).

AMENDMENT NO. 5 TO SECURITY AGREEMENT
Security Agreement • March 31st, 2015 • Upland Software, Inc. • Services-prepackaged software

This Amendment No. 5 to Security Agreement (“Amendment”) is executed as of March 23, 2015 by Upland Software III, LLC, a Delaware limited liability company f/k/a LMR Solutions LLC (“Grantor”) and Comerica Bank (“Bank”).

AMENDMENT NO. 6 TO SECURITY AGREEMENT
Security Agreement • March 31st, 2015 • Upland Software, Inc. • Services-prepackaged software

This Amendment No. 6 to Security Agreement (“Amendment”) executed as of March 23, 2015 by Upland Software II, Inc., a Delaware corporation f/k/a Tenrox Inc. (“Grantor”) and Comerica Bank (“Bank”).

AMENDMENT NO. 6 TO PLEDGE AND SECURITY AGREEMENT
Pledge and Security Agreement • March 31st, 2015 • Upland Software, Inc. • Services-prepackaged software

This Amendment No. 6 to Pledge and Security Agreement (“Amendment”) executed as of March 23, 2015 by Upland Software, Inc., a Delaware corporation f/k/a Silverback Enterprise Group, Inc. (“Grantor”) and Comerica Bank (“Bank”).

AMENDMENT NO. 6 TO SECURITY AGREEMENT
Security Agreement • March 31st, 2015 • Upland Software, Inc. • Services-prepackaged software

This Amendment No. 6 to Security Agreement (“Amendment”) is executed as of March 23, 2015 by Upland Software I, Inc., a Delaware corporation f/k/a PowerSteering Software, Inc. (“Grantor”) and Comerica Bank (“Bank”).

AMENDMENT NO. 3 TO SECURITY AGREEMENT
Security Agreement • March 31st, 2015 • Upland Software, Inc. • Services-prepackaged software

This Amendment No. 3 to Security Agreement (“Amendment”) is executed as of March 23, 2015 by Upland Software IV, Inc., a Nebraska corporation f/k/a FileBound Solutions, Inc. (“Grantor”) and Comerica Bank (“Bank”).

EIGHTH AMENDMENT TO LOAN AND SECURITY AGREEMENT, JOINDER AND CONSENT
Loan and Security Agreement • March 31st, 2015 • Upland Software, Inc. • Services-prepackaged software

This Eighth Amendment to Loan and Security Agreement, Joinder and Consent (this “Amendment”) is entered into as of March 23, 2015, between COMERICA BANK (“Bank”) and UPLAND SOFTWARE INC. f/k/a Tenrox Inc. (“Upland Canada”) (“Prior Borrower”) and SOLUTION Q INC., a corporation existing under the laws of Ontario (“Solution” and together with Prior Borrower, the “Borrowers” and each individually, a “Borrower”).

NINTH AMENDMENT TO LOAN AND SECURITY AGREEMENT, JOINDER AND CONSENT
Loan and Security Agreement • March 31st, 2015 • Upland Software, Inc. • Services-prepackaged software

This Ninth Amendment to Loan and Security Agreement, Joinder and Consent (this “Amendment”) is entered into as of March 23, 2015, among COMERICA BANK (“Bank”), UPLAND SOFTWARE, INC., a Delaware corporation f/k/a Silverback Enterprise Group, Inc. (“Upland”), UPLAND SOFTWARE I, INC., a Delaware corporation f/k/a PowerSteering Software, Inc. (“Upland I”), UPLAND SOFTWARE III, LLC, a Delaware limited liability company f/k/a LMR Solutions LLC (“Upland III), UPLAND SOFTWARE IV, INC., a Nebraska corporation f/k/a FileBound Solutions, Inc. (“Upland IV”), UPLAND SOFTWARE V, INC. a Delaware corporation f/k/a ComSci, Inc. (“Upland V”), UPLAND SOFTWARE VI, LLC, a New Jersey limited liability company f/k/a ComSci, LLC (“Upland VI”), and UPLAND SOFTWARE VII, INC., a Delaware corporation f/k/a/ Clickability, Inc. (“Upland VII”, and collectively with Upland, Upland I, Upland III, Upland IV, Upland V and Upland VI, the “Prior Borrower Group”) and UPLAND IX, LLC, a Delaware limited liability company (“U

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