OPTIONSXPRESS HOLDINGS, INC.

STOCK PURCHASE AGREEMENT

THIS OPTIONSXPRESS HOLDINGS, INC. STOCK PURCHASE AGREEMENT (the “Agreement”) is
made as of the 13th day of February, 2008, by and among Ned W. Bennett
(“Seller”) and optionsXpress Holdings, Inc., a Delaware corporation (the
“Purchaser”).

WHEREAS, Seller is the owner of/controls (directly or indirectly) 2,192,903
shares of common stock, par value $0.0001 per share (“Common Stock”), of the
Purchaser; and

WHEREAS, from time to time, Seller shall desire to sell to Purchaser and
Purchaser shall desire to purchase shares of Seller’s Common Stock, in amounts
and on dates to be mutually agreed upon by the Seller and Purchaser pursuant to
the terms and conditions set forth in this Agreement.

NOW, THEREFORE, in consideration of the above premises and mutual covenants
hereinafter set forth, the receipt and sufficiency of which are hereby
acknowledged, it is hereby agreed as follows:

1. Purchase and Sale of Common Stock. Pursuant to the terms and conditions of
this Agreement, Seller hereby agrees to sell and assign to Purchaser, and
Purchaser hereby agrees to purchase, such number of shares of Common Stock owned
or controlled by Seller (the “Acquired Common Stock”) as Seller and Purchaser
may, from time to time, mutually elect to sell and purchase, respectively;
provided, however, that the aggregate number of shares of Acquired Common Stock
shall not exceed 200,000 per year unless both parties waive such limitation.
Upon such mutual election, Seller (or such entity as Seller may control) and
Purchaser shall execute the election form attached as Annex A hereto (the “Sale
Election Form”), setting forth the number of shares to be sold/purchased and the
Consideration (as defined below).

2. Consideration. As consideration for the purchase and assignment of the
Acquired Common Stock, Purchaser shall pay to Seller a per share amount equal to
the Fair Market Value of the Acquired Common Stock (the “Consideration”). For
purposes of this Agreement, “Fair Market Value” means the average closing price
of the regular trading session reported on the Nasdaq Global Market for the
prior thirty days from the last date preceding the date on which Seller and
Purchaser execute the Sale Election Form. The Consideration shall be payable by
Purchaser to Seller by wire transfer of immediately available funds to an
account designated in writing by Seller.

3. Warranties and Representations of Seller and Purchaser. Each of Seller and
Purchaser represents and warrants that (i) it has all necessary power and
authority to enter into this Agreement, to carry out and perform his, her or its
obligations hereunder and to consummate the transactions contemplated hereby;
(ii) the execution and delivery by it of this Agreement and the consummation by
it of the transactions contemplated hereby have been duly authorized by all
necessary corporate action on the part of it (if a corporation or other entity);
(iii) this Agreement has been duly executed and delivered by it, and (assuming
due authorization, execution and delivery by each other party hereto) this
Agreement constitutes a legal, valid and binding obligation of it enforceable
against it in accordance with the terms of this Agreement.

4. Further Assurances. In connection with this Agreement and the transactions
contemplated hereby, each party agrees to execute and deliver any additional
documents and instruments and perform any additional acts that may be necessary
or appropriate to effectuate and perform the provisions of this Agreement and
those transactions.

5. Governing Law. This Agreement shall be subject to and governed by the laws of
the State of Delaware, without giving effect to its conflict of laws rules.

6. Binding Nature of Agreement. This Agreement shall be binding upon, and shall
inure to the benefit of, the heirs, successors and assigns of each of the
respective parties hereto.

7. Entire Agreement. This Agreement represents the parties’ entire agreement
with respect to its subject matter and supersedes all prior communications,
understandings and agreements with respect thereof. This Agreement may not be
amended except by written agreement executed by all parties hereto.

8. Severability. If any provisions hereof shall be or become unenforceable for
any reason, the validity and effect of all other provisions shall not be
affected thereby.

• * * *

1 IN WITNESS WHEREOF, the parties have executed this optionsXpress Holdings,
Inc. Stock Purchase Agreement of the date first above written.

PURCHASER:

OPTIONSXPRESS HOLDINGS, INC.

By: /s/ Adam DeWitt
Name: Adam DeWitt
Its: Chief Financial Officer

SELLER:

/s/ Ned W. Bennett

    Ned W. Bennett

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Annex A

SALE ELECTION FORM

Date:      

Consideration: $    per share

By executing this Sale Election Form, [ ] hereby agrees to sell      shares of
Common Stock to Purchaser, and Purchaser hereby agrees to purchase such number
of shares of Common Stock. The terms and conditions of such sale, including the
Consideration for such shares, shall be governed by the optionsXpress Holdings,
Inc. Stock Purchase Agreement, dated as of February 13, 2008 (the “Agreement”),
by and between Ned W. Bennett and Purchaser. Capitalized terms used but not
defined herein shall have the meanings assigned to such terms in the Agreement.

In connection with the sale contemplated by this Sale Election Form, [ ] hereby
warrants and represents to Purchaser, effective as of the date hereof, as
follows:

  (a)   That [ ] is the owner of the Acquired Common Stock free and clear of any
claims, liens, charges or encumbrances.  

  (b)   That [ ] has full right, power and authority to sell the Acquired Common
Stock to Purchaser and to otherwise enter into this Sale Election Form and to
consummate the transactions contemplated herein.  

  (c)   After the purchase contemplated by this Sale Election Form has been
consummated, Purchaser shall be vested with good and marketable title to the
Acquired Common Stock, free and clear of any claims, liens, charges or
encumbrances.  

  (d)   [ ] hereby directs the person charged with maintaining the Purchaser’s
books and records to record this sale on the Purchaser’s books and records as of
the date hereof.  

                 
*
  *   *  
 

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          PURCHASER:  

 
          OPTIONSXPRESS HOLDIN   GS, INC.
 
          By:      
Name:      
Its:              
     
     
 
          SELLER:  

 
          [   ]

By:     

Name:     

Its:     

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