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Exhibit 10.9

PROS Holdings, Inc.

REDEMPTION AGREEMENT

        This Redemption Agreement ("Agreement") is entered into as of March 26, 2007, by and among PROS Holdings, Inc., a Delaware corporation ("Corporation"), and the holders of the Corporation's shares of redeemable preferred stock, par value $0.001 per share (the "Redeemable Preferred Stock") set forth on Exhibit A hereto (individually, a "Seller", and together, the "Sellers"). Terms used but not defined herein have such meaning as defined in the Corporation's Certificate of Incorporation filed on August 29, 2002 (the "Certificate of Incorporation").


RECITALS

        WHEREAS, each of the Sellers owns the shares of Redeemable Preferred Stock of the Corporation set forth opposite such Seller's name on Exhibit A hereto (the "Shares");

        WHEREAS, each of the Sellers desires to tender, and Corporation desires to redeem, all Shares set forth opposite such Seller's name on Exhibit A (the "Redemption") at a price of $6.6095 per Share (the "Redemption Price");

        WHEREAS, the Redemption Price includes accrued but unpaid dividends due and payable on the Shares upon the Redemption of such Shares;

        WHEREAS, the Corporation desires to increase the size of its board of directors to six (6) members and the Sellers desire to consent to such increase subject to the execution of a mutually acceptable voting agreement among the Corporation, the Sellers and certain holders of the Corporation's capital stock;

        WHEREAS, following the Redemption, the Corporation desires to declare and pay a one-time cash dividend on the shares of the Corporation's common stock, par value $0.001 per share (the "Common Stock") in an aggregate amount of up to $41.6 million (the "Cash Dividend");

        WHEREAS, the Corporation is prohibited from declaring any dividends on the Common Stock without the consent of the Sellers holding a two-thirds of shares of capital stock held by all Sellers;

        WHEREAS, subject to the terms of hereof, the Sellers desire to permit the Corporation, following consummation of the Redemption, to declare and pay the Cash Dividend.

        NOW, THEREFORE, in consideration of the foregoing and the mutual covenants and agreements hereinafter set forth, the parties hereto agree as follows:


AGREEMENT

        1.    Recitals.    The above recitals are hereby incorporated into this Agreement in their entirety.

        2.    Redemption Date.    The Redemption Date shall be March 27, 2007 (the "Redemption Date").

        3.    Purchase of the Shares; Surrender of Certificates.    On the Redemption Date, the Corporation shall pay the respective Redemption Price, by check or wire transfer, to each Seller, and each Seller shall surrender and deliver to the Corporation the stock certificates representing the Shares for cancellation. To the extent such Shares are uncertificated, each Seller hereby authorizes the Corporation to cancel such Seller's Shares on the books of the Corporation on the Redemption Date.

        4.    Stock Power.    For value received, each of the Sellers, severally and not jointly, hereby sells, assigns and transfers unto the Corporation the Shares set forth opposite such Seller's name on

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Exhibit A standing in such Seller's name on the books of the Corporation and does hereby irrevocably constitute and appoint the Secretary of the Corporation attorney to cancel said stock on the books of the Corporation with full power of substitution in the premises and such shares of stock shall not be available for reissuance.

        5.    Representations and Warranties.    

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        6.    Cash Dividend.    Notwithstanding the provisions of Section B.3 of Article IV of the Certificate of Incorporation, the Sellers hereby authorize and approve the one-time payment by the Corporation of the Cash Dividend and all actions of the Corporation related thereto, provided that the declaration and payment of the Cash Dividend shall not occur prior to the Redemption and in any event shall occur within 30 days of the date hereof, and, subject to the foregoing conditions, the Sellers hereby waive all rights with respect to such Cash Dividend, except for such Sellers' right to receive the Cash Dividend on the Common Stock held by the Sellers. Except as expressly provided in this Agreement, nothing contained herein shall constitute a waiver or modification of any other rights, preferences and privileges any of the Sellers may have under the Certificate of Incorporation, the Corporation's By-laws or any agreements, contracts or arrangements to which any of them may be a party.

        7.    Board Increase.    Prior to the Redemption the Corporation desires to increase the size of its board of directors to six (6) members. The Sellers hereby to consent to such increase in the size of the

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board subject to the execution of a mutually acceptable voting agreement among the Corporation, the Sellers and certain holders of the Corporation's capital stock.

        8.    Entire Agreement.    This Agreement constitutes the entire agreement between the parties with respect to its subject matter and may not be modified or amended, except by written agreement of the Corporation and the Sellers holding at least a majority of the Shares as of the date of this Agreement.

        9.    Non-waiver.    No delay or failure by either party to exercise any right under this Agreement, and no partial or single exercise of that right, shall constitute a waiver of that or any other right, unless otherwise expressly provided herein.

        10.    Headings.    Headings in this Agreement are for convenience only and shall not be used to interpret or construe its provisions.

        11.    Governing Law.    This Agreement shall be construed in accordance with and governed by the laws of the State of Delaware.

        12.    Counterparts.    This Agreement may be executed in two or more counterparts, each of which shall be deemed an original but all of which together shall constitute one and the same instrument.

        13.    Binding Effect.    The provisions of this Agreement shall be binding upon and inure to the benefit of each of the parties and their respective successors and assigns.

        14.    Facsimile Signatures.    This Agreement may be executed and transmitted by facsimile, which signature shall be binding upon the parties as if they were original signatures.


Signature page follows.

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

    CORPORATION:

 

 

PROS HOLDINGS, INC.

 

 

/s/ Albert E. Winemiller

Albert E. Winemiller,
President and Chief Executive Officer


Signature page to Redemption Agreement


    SELLERS:

 

 

TA/ADVENT VIII L.P.

 

 

By: TA Associates VIII LLC, its General Partner
By: TA Associates, Inc., its Manager

 

 

By:

*


 

 

ADVENT ATLANTIC AND PACIFIC III L.P.

 

 

By: TA Associates AAP III Partners, its General Partner
By: TA Associates, Inc.

 

 

By:

*

*/s/ Kurt R. Jaggers
Kurt R. Jaggers, Attorney-in-Fact
     

 

 

TA VENTURE INVESTORS L.P.

 

 

By:

*


 

 

TA EXECUTIVES FUND LLC

 

 

By: TA Associates, Inc., its Manager

 

 

By:

*


Signature page to Redemption Agreement


    SELLERS:  

 

 

JMI EQUITY FUND III, L.P.

 

 

By:

JMI Associates III LLC, its General Partner

 

 

By:

/s/  
HARRY S. GRUNER      
      Name: Harry S. Gruner
      Title: Managing Member


Signature page to Redemption Agreement


    SELLERS:

 

 

/s/ Glenys A. Wolf

Glenys A. Wolf

 

 

/s/ William H. Wolf

William H. Wolf

 

 

/s/ Gail W. Orr

Gail W. Orr

 

 

/s/ William H. Wolf, Jr.

William H. Wolf, Jr.

 

 

/s/ Ian Ross Wolf

Ian Ross Wolf

 

 

/s/ William H. Wolf, Jr.

William H. Wolf, Jr., as Custodian under the Texas Uniform Transfers to Minors Act for Austin Everett Wolf

 

 

/s/ William H. Wolf, Jr.

William H. Wolf, Jr., as Custodian under the Texas Uniform Transfers to Minors Act for Elliot Gavin Wolf


Signature page to Redemption Agreement



EXHIBIT A


REDEEMABLE PREFERRED STOCK

 
  Shares
Outstanding

  Redemption
Price

TA/Advent VIII, L.P.   1,615,523   $ 10,677,837
Advent Atlantic and Pacific III, L.P.   303,215     2,004,107
TA Executives Fund LLC   29,711     196,376
TA Investors LLC   32,310     213,554
JMI Equity Fund, III, L.P.   625,503     4,134,277
William H. Wolf   1,051     6,947
Glenys A. Wolf   10,510     69,466
Gail W. Orr   2,102     13,893
Williams H. Wolf, Jr.   2,102     13,893
Ian Ross Wolf   1,051     6,947
William H. Wolf, Jr Custodian for:Austin Everett Wolf   2,102     13,893
William H. Wolf, Jr Custodian for:Elliott Gavin Wolf   2,102     13,893
   
 
Total   2,627,282   $ 17,365,082
   
 

Total redemption per share

 

 

 

$

6.6095
       



QuickLinks

REDEMPTION AGREEMENT
RECITALS
AGREEMENT
Signature page follows.
Signature page to Redemption Agreement
Signature page to Redemption Agreement
Signature page to Redemption Agreement
Signature page to Redemption Agreement
EXHIBIT A
REDEEMABLE PREFERRED STOCK