FOURTH AMENDMENT TO CREDIT AGREEMENT

This FOURTH AMENDMENT TO CREDIT AGREEMENT (this “Amendment”) is entered into as of April 21, 2017, by and among WELLS FARGO BANK, NATIONAL ASSOCIATION, a national banking association, as administrative agent and collateral agent for each member of the Lender Group and the Bank Product Providers (in such capacities, together with its successors and assigns in such capacities, “Agent”) and as United States administrative agent for each member of the Lender Group and the Bank Product Providers (in such capacity, together with its successors and assigns in such capacity, “US Agent”), WELLS FARGO CAPITAL FINANCE CORPORATION CANADA, an Ontario corporation, as Canadian administrative agent for each member of the Lender Group and the Bank Product Providers (in such capacity, together with its successors and assigns in such capacity, “Canadian Agent”), the Lenders (as defined in the Credit Agreement as defined below) party hereto, UPLAND SOFTWARE, INC., a Delaware corporation (“Parent”), each subsidiary of Parent identified on the signature pages hereof as a “US Borrower” (collectively, the “US Borrowers”), and UPLAND SOFTWARE INC. / LOGICIELS UPLAND INC., a Canadian federal corporation (“Upland CAD”; collectively with Parent and US Borrowers each, a “Borrower” and collectively, the “Borrowers”).

WHEREAS, the Borrowers, Agent, US Agent, Canadian Agent and the Lenders are parties to that certain Credit Agreement dated as of May 14, 2015 (as amended, restated, modified or supplemented from time to time, the “Credit Agreement”); and

WHEREAS, the Borrowers have requested that Agent and the requisite Lenders pursuant to the Credit Agreement amend the Credit Agreement in certain respects as provided herein, and Agent and Lenders have agreed to the foregoing, in each case subject to the terms and conditions contained herein.

NOW THEREFORE, in consideration of the premises and mutual agreements herein contained, the parties hereto agree as follows:

1.Defined Terms. Unless otherwise defined herein, capitalized terms used herein and not otherwise defined shall have the meanings ascribed to such terms in the Credit Agreement.

2.    Amendments to Credit Agreement. In reliance upon the representations and warranties of each Borrower set forth in Section 6 below and subject to the satisfaction of the conditions to effectiveness set forth in Section 5 below, the Credit Agreement shall be amended as follows:

(a)    Section 2.2(a) of the Credit Agreement is hereby amended and restated in its entirety as follows:

(a)    Subject to the terms and conditions of this Agreement, (i) on the Closing Date, the Lenders with a US Term Loan Commitment (as of the Closing

Date) made a term loan to the US Borrowers in the original principal amount of $19,000,000, (ii) on April 25, 2016, the Lenders with a Delayed Draw Term Loan Commitment (as of April 25, 2016) made a Delayed Draw Term Loan to the US Borrowers in the original principal amount of $10,000,000, (iii) on the Third Amendment Closing Date, the Lenders made additional term loans to the US Borrowers (according to the amounts set forth in footnote 1 on Schedule C-1 (as in effect on the Third Amendment Closing Date) in the original principal amount of $16,687,500, and (iv) on January 10, 2017, the Lenders with a Delayed Draw Term Loan Commitment (as of January 10, 2017) made a Delayed Draw Term Loan to the US Borrowers in the original principal amount of $10,000,000. Immediately prior to the effectiveness of the Fourth Amendment as of the Fourth Amendment Closing Date, the outstanding principal balance of the US Term Loan made under and as defined in this Agreement was $53,140,625 (the “Original US Term Loan”). Subject to the terms and conditions of this Agreement and the Fourth Amendment, the Lenders agree (severally, not jointly or jointly and severally) to make additional term loans in Dollars to the US Borrowers on the Fourth Amendment Closing Date in an aggregate original principal amount of $15,000,000 (together with the Original US Term Loan, the “US Term Loan”). Each Lender’s obligation to fund the portion of the US Term Loan to be funded on the Fourth Amendment Closing Date shall be limited to the amount set forth in footnote 1 on Schedule C-1 as the amount funded by it on the Fourth Amendment Closing Date.

(b)    The table set forth in Section 2.2(b) of the Credit Agreement is hereby amended and restated in its entirety as follows:

(c)    The definition of “Applicable Credit Amount Percentage” set forth on Schedule 1.1 to the Credit Agreement is hereby amended and restated in its entirety as follows:

“Applicable Credit Amount Percentage” means the percentage set forth in the following table for the applicable period set forth opposite thereto:

(d)    The definition of “Delayed Draw Term Loan Commitment Termination Date” is hereby amended to delete the reference therein to “November 15, 2018” and insert in lieu thereof a reference to “Fourth Amendment Closing Date”.

(e)    Clause (b) of the definition of “Permitted Acquisition” set forth on Schedule 1.1 to the Credit Agreement is hereby amended and restated in its entirety as follows:

(b)    no Indebtedness will be incurred, assumed, or would exist with respect to Parent or its Subsidiaries as a result of such Acquisition, other than Indebtedness permitted under clauses (a), (f), (g), (m), (n), or (q) of the definition of Permitted Indebtedness, and no Liens will be incurred, assumed, or would exist with respect to the assets of Parent or its Subsidiaries as a result of such Acquisition other than Permitted Liens,

(f)    Clause (e) of the definition of “Permitted Acquisition” set forth on Schedule 1.1 to the Credit Agreement is hereby amended and restated in its entirety as follows:

(e) (i) Borrowers shall have Availability plus Qualified Cash in an amount equal to or greater than $10,000,000 immediately after giving effect to the consummation of the proposed Acquisition; (ii) US Borrowers shall have US Availability plus US Qualified Cash in an amount equal to a greater than $9,000,000 immediately after giving effect to the consummation of the proposed Acquisition; and (iii) Canadian Borrowers shall have Canadian Availability plus Canadian Qualified Cash in an amount equal to or greater than $1,000,000 immediately after giving effect to the consummation of the proposed Acquisition,

(g)    Clause (k) of the definition of “Permitted Acquisition” set forth on Schedule 1.1 to the Credit Agreement is hereby amended and restated in its entirety as follows:

(k)    the purchase consideration payable in respect of all Permitted Acquisitions occurring on or after the Fourth Amendment Closing Date (excluding the RightAnswers Merger but including the proposed Acquisition and including deferred payment obligations) shall not exceed $75,000,000 in the aggregate; provided, that the purchase consideration payable in respect of any single Acquisition or series of related Acquisitions shall not exceed $20,000,000 in the aggregate.

(h)    Schedule 1.1 to the Credit Agreement is hereby amended by adding the following defined terms in alphabetical order:

“Fourth Amendment” means that certain Fourth Amendment to Credit Agreement, dated as of the Fourth Amendment Closing Date, by and among the Borrowers, Agent and the Lenders party thereto.

“Fourth Amendment Closing Date” means April 21, 2017.

“RA Acquisition” means RA Acquisition Corporation I, a Delaware corporation and wholly-owned Subsidiary of Parent.

“RightAnswers Merger” means the merger of RA Acquisition with and into RightAnswers Target with RightAnswers Target as the surviving corporation, pursuant to and in accordance with the RightAnswers Merger Agreement.

“RightAnswers Merger Agreement” that certain Agreement and Plan of Merger dated as of April 7, 2017 by and among Parent, RA Acquisition, RightAnswers Target, and Shareholder Representative Services LLC, a Colorado limited liability company solely in its capacity as stockholder representative.

“RightAnswers Target” means RightAnswers, Inc., a Delaware corporation.

(i)    Schedule C-1 to the Credit Agreement is hereby amended and restated in its entirety as set forth on Exhibit A attached hereto.

3.    Continuing Effect. Except as expressly set forth in Sections 2 and 3 of this Amendment, nothing in this Amendment shall constitute a waiver or other modification of any other terms or provisions of the Credit Agreement or any other Loan Document, and the Credit Agreement and the other Loan Documents shall remain unchanged and shall continue in full force and effect, in each case as amended hereby. This Amendment is a Loan Document.

4.    Reaffirmation and Confirmation. Each Borrower hereby ratifies, affirms, acknowledges and agrees that the Credit Agreement and the other Loan Documents to which it is a party represent the valid, enforceable and collectible obligations of such Borrower, and further acknowledges that there are no existing claims, defenses, personal or otherwise, or rights of setoff whatsoever with respect to the Credit Agreement or any other Loan Document as of the date hereof. Each Borrower hereby agrees that this Amendment in no way acts as a release or relinquishment of the Liens and rights securing payments of the Obligations. The Liens and rights securing payment of the Obligations are hereby ratified and confirmed by each Borrower in all respects.

5.    Conditions to Effectiveness. This Amendment shall become effective upon the satisfaction of each of the following conditions precedent, in each case satisfactory to Agent in all respects:

(a)    Agent shall have received a copy of this Amendment executed and delivered by the Lenders, and each Borrower, and each agreement, document and instrument set forth on the Closing Checklist attached hereto as Exhibit B;

(b)    after giving effect to the making of the Loans and other extensions of credit to be advanced by the Lenders to the Borrowers, any prepayment of Loans to be made on the date hereof, and the payment of all fees and expenses required to be paid by the Borrowers under this Amendment, the Credit Agreement and the other Loan Documents on the date hereof, Borrowers have Availability, plus Qualified Cash, that exceeds $20,000,000;

(c)    after giving effect to the making of the Loans and other extensions of credit to be advanced by the Lenders to the Borrowers on the date hereof and any prepayment of Loans to be made on the date hereof, the ratio of (x) Obligations outstanding as of the date hereof to (y) EBITDA for the 12 month period ended December 31, 2016, is not greater than 3.50:1.00;

(d)    Agent shall have received payment of all fees, expenses, and other amounts due and payable on the date hereof under each Loan Document, including without limitation, all fees and expenses pertaining to this Amendment and all amounts due and payable pursuant to the Fourth Amendment Fee Letter of even date herewith among Borrowers and Agent;

(e)    no Default or Event of Default shall have occurred and be continuing on the date hereof or as of the date of the effectiveness of this Amendment;

(f)    Agent shall have received evidence in form satisfactory to it that the Acquisition contemplated by the RightAnswers Merger Agreement shall have been consummated on or prior to the date hereof in accordance with the RightAnswers Merger Agreement, all agreements, documents and instruments executed and/or delivered in connection therewith (collectively, with the RightAnswers Merger Agreement, the “RightAnswers Merger Documents”), and all applicable requirements of law, and no terms or conditions of the RightAnswers Merger Documents (other than any immaterial terms or conditions) shall have been waived without the consent of Agent;

6.    Representations and Warranties. In order to induce Agent and Lenders to enter into this Amendment, each Borrower hereby represents and warrants to Agent and Lenders that:

(a)    after giving effect to this Amendment, all representations and warranties contained in the Loan Documents to which such Borrower is a party are true and correct in all material respects (except that such materiality qualifier shall not be applicable to any representations and warranties that already are qualified or modified by materiality in the text thereof) on and as of the date of this Amendment, as though made on and as of such date (except to the extent that such representations and warranties relate solely to an earlier date, in which case such representations

and warranties shall be true and correct in all material respects (except that such materiality qualifier shall not be applicable to any representations and warranties that already are qualified or modified by materiality in the text thereof) on and as of such earlier date);

(b)    no Default or Event of Default has occurred and is continuing;

(c)    this Amendment and the Loan Documents, as amended hereby, constitute legal, valid and binding obligations of such Borrower and are enforceable against such Borrower in accordance with their respective terms, except as enforcement may be limited by equitable principles or by bankruptcy, insolvency, reorganization, moratorium or similar laws relating to or limiting creditors’ rights generally; and

(d)    as of the Fourth Amendment Closing Date, the RightAnswers Merger has been consummated (or is being consummated contemporaneously with the credit extension under the Credit Agreement on the Fourth Amendment Closing Date) in accordance with the RightAnswers Merger Documents and all applicable requirements of law, and no terms or conditions of the RightAnswers Merger Documents (other than any immaterial terms or conditions) have been waived without the consent of Agent.

7.    Post-Closing Covenants.

(a)    Within 10 Business Days of the date hereof (or such later date as permitted by Agent in its reasonable discretion), Borrowers shall deliver to Agent certificates of status with respect to Ultriva, LLC issued by the appropriate officer of each of (i) the State of Illinois, (ii) the State of Virginia, and (iii) the State of North Carolina, and indicating that Ultriva, LLC is in good standing in such jurisdiction and registered to do business in each such jurisdiction under its legal name.

(b)    Within 30 days of the date hereof (or such later date as permitted by Agent in its reasonable discretion), Borrowers shall deliver to Agent evidence of the filing of trademark security interest releases with respect to each of (i) that certain Intellectual Property Security Agreement, dated as of October 2, 2007, by and between RightAnswers, Inc. and Silicon Valley Bank, (ii) that certain Security Agreement dated as of December 10, 1999, by and between Serviceware, Inc. (predecessor in interest to certain Trademarks being acquired in connection with the RightAnswers Merger Agreement) and PNC Bank, National Association and (iii) that certain Security Agreement dated as of November 21, 1997, by and between Serviceware, Inc. (predecessor in interest to certain Trademarks being acquired in connection with the RightAnswers Merger Agreement) and PNC Bank, National Association, in each case, in form and substance satisfactory to Agent.

(c)    Within 30 days of the date hereof (or such later date as permitted by Agent in its sole discretion), Borrowers shall comply with Sections 5.11 and 5.12 of the Credit Agreement with respect to the formation of RA Acquisition Corporation I, a Delaware corporation, and the acquisition of RightAnswers, Inc., a Delaware corporation.

(d)    Within 30 days of the date hereof (or such later date as permitted by Agent in its sole discretion), Borrowers shall deliver to Agent a fully executed Control Agreement from CIT Bank, N.A. with respect to each Deposit Account maintained by any Loan Party at CIT Bank, N.A., except to the extent otherwise excused by Section 7(k)(iv) of the US Guaranty and Security Agreement or the Canadian Guarantee and Security Agreement.

(e)    Within 90 days of the date hereof (or such later date as permitted by Agent in its sole discretion), Borrowers shall either (i) deliver to Agent a fully executed Control Agreement from Bank of America with respect to each Deposit Account maintained by any Loan Party at Bank of America (except to the extent otherwise excused by Section 7(k)(iv) of the US Guaranty and Security Agreement or the Canadian Guarantee and Security Agreement) or (ii) close each Deposit Account maintained by any Loan Party at Bank of America; provided that, from the date hereof until the earlier of (x) the delivery of such Control Agreement and (y) the closure of such Deposit Accounts, the Loan Parties shall not permit the aggregate amount on deposit in such Deposit Accounts to exceed $250,000 at any one time.

Failure to comply with any covenant in this Section 7 shall constitute an immediate Event of Default.

8.    Miscellaneous.

(a)    Choice of Law and Venue; Jury Trial Waiver; Reference Provision. Without limiting the applicability of any other provision of the Credit Agreement or any other Loan Document, the terms and provisions set forth in Section 12 of the Credit Agreement are expressly incorporated herein by reference.

(b)    Counterparts. This Amendment may be executed in any number of counterparts, and by the parties hereto on the same or separate counterparts, and each such counterpart, when executed and delivered, shall be deemed to be an original, but all such counterparts shall together constitute but one and the same Amendment.

(c)    No Novation. The parties hereto acknowledge and agree that: (i) this Amendment and any other document or instrument executed and delivered in connection herewith do not constitute and shall in no event be deemed to be a compromise, satisfaction, reinstatement, accord and satisfaction, novation, release or termination of the Obligations as in effect prior to the Fourth Amendment Closing Date, or of any the Loan Documents or any rights or obligations thereunder, or a waiver by Agent or Lenders of any of their rights under this Amendment or the other the Loan Documents, whether at law or in equity or otherwise; (ii) the Obligations are in all respects continuing with only the terms thereof being modified to the extent expressly provided in this Amendment; and (iii) the guarantees and the Liens and security interests as granted or purported to be granted under or pursuant to the Credit Agreement and the other Loan Documents securing payment of the Obligations are in all such respects continuing in full force and effect and secure the payment of the Obligations as provided therein.

9.    Release.

(a)    In consideration of the agreements of Agent and Lenders contained herein and for other good and valuable consideration, the receipt and sufficiency of which is hereby acknowledged, each Borrower, on behalf of itself and its successors, assigns, and other legal representatives (each Borrower and all such other Persons being hereinafter referred to collectively as the “Releasors” and individually as a “Releasor”), hereby absolutely, unconditionally and irrevocably releases, remises and forever discharges Agent and Lenders, and their successors and assigns, and their present and former shareholders, affiliates, subsidiaries, divisions, predecessors, directors, officers, attorneys, employees, agents and other representatives (Agent, each Lender and all such other Persons being hereinafter referred to collectively as the “Releasees” and individually as a “Releasee”), of and from all demands, actions, causes of action, suits, covenants, contracts, controversies, agreements, promises, sums of money, accounts, bills, reckonings, damages and any and all other claims, counterclaims, defenses, rights of set-off, demands and liabilities whatsoever (individually, a “Claim” and collectively, “Claims”) of every name and nature, known or unknown, suspected or unsuspected, both at law and in equity, which any Releasor may now own, hold, have or claim to have against the Releasees or any of them for, upon, or by reason of any circumstance, action, cause or thing whatsoever which arises at any time on or prior to the day and date of this Amendment, in any way related to or in connection with the Credit Agreement, or any of the other Loan Documents or transactions thereunder or related thereto.

(b)    Each Borrower understands, acknowledges and agrees that the release set forth above may be pleaded as a full and complete defense and may be used as a basis for an injunction against any action, suit or other proceeding which may be instituted, prosecuted or attempted in breach of the provisions of such release.

(c)    Each Borrower agrees that no fact, event, circumstance, evidence or transaction which could now be asserted or which may hereafter be discovered shall affect in any manner the final, absolute and unconditional nature of the release set forth above.

IN WITNESS WHEREOF, the parties hereto have caused this Agreement to be executed and delivered as of the date first above written.

II.    Counsel to Parties:

III.    Closing Documents [each to be executed/completed/delivered in connection with the “Effective Time” of the Agreement and Plan of Merger, except for the Consent under Credit Agreement which is to be executed in connection with the execution of the Agreement and Plan of Merger]: