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                                                                   Exhibit 10.14

                                                    January 15, 2004

Mr. Ned W. Bennett
200 Granada Avenue
El Paso, Texas 79912

     Re:    Employment Letter Agreement
            ---------------------------

Dear Ned:

     In keeping with our discussions, this letter agreement memorializes the
terms of your continued employment with optionsXpress, Inc. (the "Company").

     1.     TITLES AND DUTIES. Your title will be Chief Executive Officer, and
you will report directly to the Board of Directors of the Company (the "Board").
As such, you will be responsible for performing such duties and responsibilities
as are customarily assigned to such position, and to perform such other services
as assigned from time to time by the Board, not inconsistent with your position.
You will be expected to devote your full business time and attention to the
business of the Company and the performance of your duties.

     2.     COMPENSATION; TERM. You will receive an annual base salary of
$172,000 (the "Base Salary") paid in accordance with the payroll procedures of
the Company, with annual increases (but not decreases) as may be determined by
the Compensation Committee of the Board in its discretion. The Base Salary
payable hereunder, as may be increased from time to time, and any other amounts
payable to you under this Agreement (including, without limitation, pursuant to
Section 3 and Section 4 below), shall be subject to applicable withholding and
payroll taxes, and such other deductions as may be required under the Company's
employee benefit plans. The term of your employment under this letter agreement
shall begin on the date hereof and shall continue until terminated in accordance
with Section 5 below.

     3.     BONUSES. Unless the Board or the Compensation Committee thereof
determines in good faith that you and/or the Company had significant performance
issues, during the term of your employment you will be eligible to receive
annual bonuses under, and historically consistent with, the Company's bonus
plans for senior level executives, and the grant and payment terms and the
amount of any such bonuses shall be determined by the Compensation Committee of
the Board. Your bonus opportunity shall be at least equal to the opportunities
provided to you under the Company's current and historical bonus plans for
senior level executives.

     4.     EMPLOYEE BENEFITS. During the term of your employment, you will be
entitled to participate in all employee welfare benefit plans of the Company
applicable to senior level executives. In addition, during the term of your
employment, you will be entitled to three (3) weeks paid vacation per year.
Further, you shall be entitled to reimbursement for expenses incurred by you in
the ordinary course of the Company's business (subject to the Company's policies
with respect to reporting and documentation of such expenses).

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     5.     TERMINATION AND SEVERANCE.

            (a)    During the term of employment hereunder, your employment may
     be terminated as follows:

                   (i)     At any time upon prior written notice by the Company
                           for any reason other than Cause (as defined below) or
                           no reason ("Termination Without Cause").

                   (ii)    At any time upon three (3) months prior written
                           notice by you for any reason other than Good Reason
                           (as defined below) or no reason.

                   (iii)   Automatically in the event of (A) your death or (B)
                           your inability to perform the essential duties,
                           responsibilities and functions of your position with
                           the Company as a result of any mental or physical
                           incapacity, even with reasonable accommodations for
                           such disability or incapacity provided by the
                           Company, which inability lasts (or is likely to last,
                           based on competent medical evidence presented to the
                           Board) for a continuous period of six (6) months or
                           longer. The reasoned and good faith judgment of the
                           Board as to your mental or physical inability to
                           perform shall be final so long as such judgment is
                           based on competent medical evidence presented to the
                           Board by you and by any physician or group of
                           physicians engaged by you or the Board to advise the
                           Board on such matters.

                   (iv)    Immediately upon written notice by the Company if
                           such termination is for Cause ("Termination for
                           Cause").

                   (v)     Immediately upon written notice by you if such
                           termination is for Good Reason.

                   (vi)    At any time by mutual written agreement between you
                           and the Company.

            (b)    Upon termination of your employment hereunder for any reason,
     all obligations of the Company shall cease upon such termination, except
     the Company's obligations to (i) pay the compensation set forth in Section
     2 hereof through the date of such termination, (ii) provide the benefits
     set forth in Section 4 hereof through the date of such termination and to
     comply with all state and federal laws and regulations applying to such
     benefits and (iii) pay the severance benefits, if applicable, to you
     pursuant to the terms and conditions set forth in Section 5(c) below. In
     the event that your employment is terminated by you without Good Reason or
     as a result of a Termination for Cause by the Company, you shall not be
     entitled to any bonus compensation in respect of the calendar year of your
     termination.

            (c)    In the event that your employment is terminated for Good
     Reason or as a result of a Termination Without Cause, you shall be entitled
     to receive an amount equal

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     to twelve (12) months severance pay at the monthly rate of your
     then-current base salary, payable in twelve (12) equal monthly installments
     following such termination, unless increased pursuant to the terms of
     Section 5(f) below, if and only if (i) you have executed and delivered to
     the Company a mutual general release of all claims against you, on the one
     hand, and the Company and its directors, officers and affiliates, on the
     other hand, which general release shall be in the form of EXHIBIT A
     attached hereto, and (ii) subsequent to such termination, you shall not
     have (A) revoked or breached the provisions of such general release or
     breached or otherwise failed to comply with the provisions of Sections 6, 7
     or 8 of this letter agreement, or (B) applied for unemployment compensation
     chargeable to the Company during such severance period.

            (d)    For purposes hereof, the term "Cause" means the following:
     (i) the commission of fraud, theft or embezzlement by you in connection
     with your duties to the Company or any of its customers or other material
     business relations; (ii) your conviction of (or entry of a plea of guilty
     or NOLO CONTENDERE to) a felony (other than minor traffic violations) (A)
     in connection with your duties to the Company or any of its customers or
     other material business relations, or (B) that materially and adversely
     effects your ability to continue in your position and fulfill your duties
     to the Company under applicable laws and regulations; (iii) your gross
     mismanagement demonstrably and materially injurious to the Company, which
     is not cured within thirty (30) days after a written demand is delivered to
     you by the Board which identifies the grounds therefor; (iv) any material
     breach by you of the provisions of this letter agreement (including any
     breach by you of the provisions set forth in Sections 6, 7 or 8 hereof) or
     any other material breach of any other agreement between or among you and
     the Company, in either event which breach has not been cured within thirty
     (30) days after a written demand is delivered to you by the Board which
     identifies the grounds therefor. Any disagreement concerning whether there
     has been "Cause" for termination will be resolved by the Board in its sole
     discretion acting in good faith after providing you an opportunity to
     address the Board at a full meeting thereof regarding whether or not there
     has been "Cause" for termination.

            (e)    For purposes hereof, the term "Good Reason" means your
     termination of employment with the Company as a result of the following:
     (i) a material adverse alteration in the nature or status of your position,
     duties or responsibilities with the Company without your prior written
     consent; or (ii) the failure of the Company to comply in any material
     respect with any of its obligations hereunder or under any other agreements
     with you which remains uncured for a period of thirty (30) days following
     your written notice to the Company of such failure.

            (f)    In the event your employment with the Company is terminated
     for any reason, the Company shall have the option to elect in writing
     within sixty (60) days after the date of termination to pay you, in equal
     monthly installments, an additional amount equal to your then-current base
     salary for up to twenty-four (24) additional months following the
     Noncompetition Period, with any such additional period being referred to
     herein as the "Additional Restriction Period" (which amount shall be in
     addition to any other amounts payable to you under Section 5(c) hereof). If
     the Company makes such election then the restrictions contained in Sections
     7(a) and (b) hereof shall commence on the date of such termination and
     extend for the Additional Restriction Period. In the event the Company
     fails to make such election in the manner and during the time period

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     set forth above, then the Company shall be deemed to have waived its rights
     to make an election under this Section 5(f).

     6.     CONFIDENTIALITY.

            (a)    You will not at any time during or after termination of your
     employment with the Company disclose to anyone or make use of, directly or
     indirectly, any Confidential Information (as defined below). All records of
     every nature and description relating to the Company's business during your
     employment, whether or not prepared by you, shall be and remain the
     property of the Company. All records of every nature and description
     relating to the Company's business during your employment shall be left
     with or delivered to the Company upon termination of your employment.

            (b)    For purposes of this letter agreement, "Confidential
     Information" means all information of a confidential or proprietary nature
     (whether or not specifically labeled or identified as "confidential"), in
     any form or medium, that relates to the Company or its subsidiaries or
     their business relations and their respective business activities and
     includes, without limitation, the following: (i) internal business
     information (including historical and projected financial information and
     budgets and information relating to strategic and staffing plans and
     practices, business, training, marketing, promotional and sales plans and
     practices, cost, rate and pricing structures and accounting and business
     methods); (ii) identities and individual requirements of, and specific
     contractual arrangements with, the Company's and its subsidiaries'
     customers, employees, independent contractors, clearing agencies, joint
     venture partners and other business relations and their confidential
     information; (iii) trade secrets, know-how, compilations of data and
     analyses, techniques, systems, formulae, research, records, reports,
     manuals, documentation, models, data and data bases relating thereto; (iv)
     inventions, innovations, improvements, developments, methods, designs,
     analyses, drawings, reports and all similar or related information (whether
     or not patentable); and (v) information related to any and all intellectual
     and proprietary property and rights and rights in Confidential Information
     of every kind and description anywhere in the world, including all (A)
     patents, patent applications, patent disclosures and inventions, (B)
     internet domain names, trademarks, service marks, trade dress, trade names,
     logos and corporate names and registrations and applications for
     registration thereof together with all of the goodwill associated
     therewith, (C) copyrights (registered or unregistered) and copyrightable
     works and registrations and applications for registration thereof, (D) mask
     works and registrations and applications for registration thereof, (E)
     computer software, data, data bases and documentation thereof, (F) trade
     secrets and other Confidential Information (including ideas, formulas,
     compositions, inventions (whether patentable or unpatentable and whether or
     not reduced to practice), know-how, manufacturing and production processes
     and techniques, research and development information, drawings,
     specifications, designs, plans, proposals, technical data, copyrightable
     works, financial and marketing plans and customer and supplier lists and
     information), (G) other intellectual property rights and (H) copies and
     tangible embodiments thereof (in whatever form or medium).

            (c)    Notwithstanding the provisions of this Section 6, information
     shall not be deemed "Confidential Information" for purposes hereof if such
     information is (i) in the

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     public domain (other than as a result of a breach of this Agreement by
     you), (ii) approved for release by the Company or (iii) lawfully obtained
     by you after termination of your employment with the Company from third
     parties (other than the Company or any of its affiliates or any of their
     respective employees, directors or representatives) on a nonconfidential
     basis who, to your knowledge, are not prohibited from disclosing such
     information to you by a legal, contractual or fiduciary obligation to the
     Company or any of its affiliates.

     7.     NONCOMPETITION; NONSOLICITATION.

            (a)    You acknowledge that (i) you are one of the Company's
     founders and that you are familiar with the Company's trade secrets and
     with other confidential information concerning the Company, including the
     Company's (A) inventions, technology and research and development, (B)
     customers and vendors and customer and vendor lists, (C) products and
     services (including those under development) and related costs and pricing
     structures, (D) accounting and business methods and practices, and (E)
     similar and related confidential information and trade secrets; (ii) your
     services have been and shall continue to be of special, unique and
     extraordinary value to the Company and that you have been substantially
     responsible for the growth and development of the Company and the creation
     and preservation of the Company's goodwill; and (iii) the Company would be
     irreparably damaged (including a significant loss of goodwill) if you were
     to provide similar services to any person or entity competing with the
     Company or engaged in a similar business. You further acknowledge that the
     execution and delivery of this Agreement was a material inducement to the
     Purchasers (as defined therein) and the Company to enter into the Stock
     Purchase and Recapitalization Agreement dated as of December 17, 2003 (the
     "Recapitalization Agreement") and part of the consideration for the
     Repurchase Price paid to you thereunder. Due to your access to the
     confidential proprietary information, customer information and customer
     relationships and uniqueness of your services to the Company and the
     consideration you received under the Recapitalization Agreement as
     described and acknowledged in the preceding sentences, and in consideration
     of the Company's agreements herein, you agree that for the longer of (x)
     three (3) years from the date of the closing under the Recapitalization
     Agreement and (y) the term of your employment with the Company and a period
     of one (1) year after termination of your employment as provided hereunder
     (the "Noncompetition Period"), unless such one (1) year period is extended
     pursuant to the provisions of Section 5(f) above, you shall not directly or
     indirectly, either for yourself or for any other individual, corporation,
     partnership, joint venture or other entity, own any interest in, manage,
     control, participate in (whether as an officer, director, employee,
     partner, agent, representative or otherwise), consult with or render
     services for any entity that (in whole or in part) engages or proposes to
     engage in, or in any other manner engage, anywhere in the world, in the
     on-line securities industry for the retail, consumer customer base
     (including, for the avoidance of doubt and without limitation, the service
     of retail brokerage accounts through independent representatives) or any
     other business conducted by the Company or any of its subsidiaries during
     your employment term or proposed to be conducted by the Company or any of
     its subsidiaries within the six (6) month period prior to the termination
     of your employment; PROVIDED, HOWEVER, that nothing herein shall prohibit
     you from being a passive owner of not more than ten percent (10%) of the

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     outstanding stock of any class of a corporation which is publicly traded so
     long as you do not have any active participation in the business of such
     corporation.

            (b)    During the Noncompetition Period, you shall not directly or
     indirectly (through any other individual, corporation, partnership, joint
     venture or other entity or otherwise) (i) induce or attempt to induce any
     employee of the Company or any of its subsidiaries to leave the employ of
     the Company or any of its subsidiaries, or in any way interfere with the
     relationship between the Company or any of its subsidiaries and any
     employee thereof, (ii) hire any person who was an employee of the Company
     or any of its subsidiaries at any time during the six (6) month period
     immediately prior to the date on which such hiring would take place, or
     (iii) call on, solicit or service any customer, supplier, licensee,
     licensor or other business relation of the Company or any of its
     subsidiaries in order to induce or attempt to induce such person to cease
     doing business with the Company or any of its subsidiaries, or in any way
     interfere with the relationship between any such customer, supplier,
     licensee or business relation and the Company or any of its subsidiaries.
     Each of you and the Company (on behalf of itself and its subsidiaries)
     mutually agree not to make any negative statements or communications about
     the other and, in the case of the Company, about any of its subsidiaries.

            (c)    If, at the time of enforcement of the covenants contained in
     this Section 7 (the "Restrictive Covenants"), a court shall hold that the
     duration, scope or area restrictions stated herein are unreasonable under
     circumstances then existing, you agree that the maximum duration, scope or
     area reasonable under such circumstances shall be substituted for the
     stated duration, scope or area and that the court shall be allowed and
     directed to revise the restrictions contained herein to cover the maximum
     period, scope and area permitted by law. You acknowledge that you have
     consulted with legal counsel regarding the Restrictive Covenants and, based
     on such consultation, have determined and hereby acknowledge that the
     Restrictive Covenants are reasonable in terms of duration, scope and area
     restrictions and are necessary to protect the goodwill of the Company's
     business and the on-line nature of the Company's business is such that it
     is not conducted with respect to geographical boundaries.

            (d)    If you breach, or threaten to commit a breach of, any of the
     Restrictive Covenants, the Company shall have the right and remedy to have
     the Restrictive Covenants specifically enforced by any court of competent
     jurisdiction, it being agreed that any breach or threatened breach of the
     Restrictive Covenants would cause irreparable injury to the Company and
     that money damages would not provide an adequate remedy to the Company.

            (e)    In the event of any breach or violation by you of any of the
     Restrictive Covenants, the time period of such covenant shall be tolled
     until such breach or violation is resolved.

     8.     THE COMPANY'S OWNERSHIP OF INTELLECTUAL PROPERTY.

            (a)    In the event that you, as part of your activities on behalf
     of the Company or any of its subsidiaries generate, author or contribute to
     (whether before or after the date of this letter agreement) any invention,
     design, new product or service development,

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     device, product, method or process (whether or not patentable or reduced to
     practice or comprising Confidential Information), any copyrightable work
     (whether or not comprising Confidential Information) or any other form of
     Confidential Information relating directly or indirectly to the Company's
     or any of its subsidiaries' business as now or hereinafter conducted (the
     "Intellectual Property"), you acknowledge that such Intellectual Property
     is the exclusive property of the Company and hereby assign all right, title
     and interest in and to such Intellectual Property to the Company. Any
     copyrightable work prepared in whole or in part by you will be deemed "a
     work made for hire" under Section 201(b) of the 1976 Copyright Act, and the
     Company shall own all of the rights comprised in the copyright therein. You
     shall promptly and fully disclose to the Company all Intellectual Property
     not generally known to the Company through the ordinary course of operation
     of the business, and you shall cooperate with the Company to protect the
     Company's interests in and rights to such Intellectual Property (including,
     without limitation, providing reasonable assistance in securing patent
     protection and copyright registrations and executing all documents as
     reasonably requested by the Company, whether such requests occur prior to
     or after termination of your employment with the Company). The Company
     agrees to pay you for any reasonable costs, fees and expenses incurred by
     you for providing your assistance pursuant to this Section 8, including,
     but not limited to, any of your costs, expenses and your hourly fees if
     such assistance is provided after your termination for any reason.

            (b)    In accordance with Section 2872 of the Illinois Employee
     Patent Act, III. Rev. Stat. Chap. 140, Section 301 et seq. (1983), you are
     hereby advised that Section 8 of this Agreement regarding the Company's
     ownership of Intellectual Property does not apply to any invention for
     which no equipment, supplies, facilities or trade secret information of the
     Company was used and which was developed entirely on your own time, unless
     (i) the invention relates to the business of the Company or any of its
     subsidiaries or to the Company's or any of its subsidiaries actual or
     demonstrably anticipated research or development or (ii) the invention
     results from any work performed by you for or on behalf of the Company or
     any of its subsidiaries.

     9.     BINDING EFFECT. The terms hereof shall be binding upon and shall
inure to the benefit of you and the Company, the successors and assigns of the
Company, and the heirs, executors, administrators, legal representatives and
assigns of you, PROVIDED THAT your rights and obligations hereunder may not be
delegated or assigned.

     10.    ENTIRE AGREEMENT. This letter agreement shall supersede any former
oral agreement and any former written agreement heretofore executed relating
generally to your employment with the Company, and this letter agreement can
only be amended, altered or terminated and its provisions can only be waived by
an agreement in writing signed by you and the Company; PROVIDED, HOWEVER, that,
except for the definition of "Cause" in Section 5(d) hereof, this letter
agreement shall not be deemed to supersede any restricted stock, equity award or
other agreement between the Company and you.

     11.    REPRESENTATIONS. You hereby represent and warrant to the Company
that (a) the execution, delivery and performance of this Agreement by you does
not and shall not conflict with, breach, violate or cause a default under any
contract, agreement, instrument, order, judgment or decree to which your are a
party or by which your are bound, (b) you are not a party

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to or bound by any employment agreement, noncompete agreement or confidentiality
agreement with any person or entity other than the Company and/or its
subsidiaries and (c) upon the execution and delivery of this Agreement by the
Company, this Agreement shall be the valid and binding obligation of you,
enforceable in accordance with its terms. You hereby acknowledge and represent
that you have consulted with independent legal counsel regarding your rights and
obligations under this Agreement and that you fully understand the terms and
conditions contained herein.

     12.    COOPERATION. During the term of your employment and for a period of
two (2) years after termination of your employment for any reason, you shall
reasonably cooperate with the Company in (a) any internal investigation or any
administrative, regulatory or judicial proceeding (so long as such investigation
or proceeding is not adversarial in nature between you and the Company) or (b)
any dispute with a third party, as reasonably requested by the Company
(including, without limitation, being available to the Company upon reasonable
advance notice for interviews and factual investigations, appearing at the
Company's request to give testimony without requiring service of a subpoena or
other legal process, volunteering to the Company all pertinent information and
turning over to the Company all relevant documents which are or may come into
your possession, all at times and on schedules that are reasonably consistent
with your other activities and commitments). In the event the Company requires
your cooperation in accordance with this Section, the Company shall reimburse
you for all reasonable travel and other out-of-pocket expenses (including
lodging and meals) incurred by you in connection therewith promptly upon
submission of receipts therefor.

     13.    REMEDIES. In the event that you violate any of the provisions
hereof, you hereby acknowledge that the Company will suffer irreparable damages
and will be entitled to full injunctive relief or such other relief against you
as may be provided by law or in equity.

     14.    ENFORCEABILITY. This letter agreement shall be construed and
enforced under the laws of the State of Illinois without giving effect to the
principles of conflicts of laws thereof. If any provision of this letter
agreement is held invalid or unenforceable by operation of law or otherwise,
such circumstances shall not have the effect of rendering any of the other
provisions of this letter agreement invalid or unenforceable.

                            [SIGNATURE PAGE FOLLOWS]

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                 [SIGNATURE PAGE TO EMPLOYMENT LETTER AGREEMENT]

     By signing below, the Company agrees to all of the terms and conditions of
this letter agreement. Please indicate your acceptance of these terms and
conditions by signing each enclosed copy of this letter agreement where
indicated below, and return an originally-executed copy of this letter agreement
to the undersigned.

                                       Sincerely yours,

                                       optionsXpress, Inc.

                                       By: /s/ David Kalt
                                           -------------------------------------
                                             David Kalt, President

ACCEPTED AND AGREED as of
this 15th day of January, 2004.

/s/ Ned W. Bennett
-------------------------------
Ned W. Bennett<Page>

                                                                   Exhibit 10.15

                                              July 15, 2004
Mr. David Fisher
c/o optionsXpress Holdings, Inc.
39 S. LaSalle St., Suite 220
Chicago, Illinois 60603

     Re:  Employment Letter Agreement
          ---------------------------

Dear David:

     In keeping with our discussions, this letter agreement memorializes the
terms of your employment with optionsXpress Holdings, Inc. (the "Company").

     1.   TITLES AND DUTIES. Your title will be Chief Financial Officer, and you
will report to the Chairman and the Chief Executive Officer of the Company. As
such, you will be responsible for performing such duties and responsibilities as
are customarily assigned to such position, and to perform such other services as
assigned from time to time by the Chairman and/or the Chief Executive Officer,
not inconsistent with your position. You will be expected to devote your full
business time and attention to the business of the Company and the performance
of your duties.

     2.   COMPENSATION; TERM. You will receive an annual base salary of $300,000
(the "Base Salary") paid in accordance with the payroll procedures of the
Company, with annual increases (but not decreases) as may be determined by the
Compensation Committee of the Board of Directors of the Company (the
"Compensation Committee") in its discretion. The Base Salary payable hereunder,
as may be increased from time to time, and any other amounts payable to you
under this Agreement (including, without limitation, pursuant to Sections 3, 4
and 5 below), shall be subject to applicable withholding and payroll taxes, and
such other deductions as may be required under the Company's employee benefit
plans. The term of your employment under this letter agreement shall be deemed
to have commenced on July 26, 2004 and shall continue until terminated in
accordance with Section 6 below.

     3.   BONUSES.

          (a)  Unless the Board of Directors of the Company (the "Board") or the
     Compensation Committee thereof determines in good faith that you and/or the
     Company had significant performance issues, during the term of your
     employment you will be eligible to receive annual bonuses of up to 100% of
     your Base Salary under, and historically consistent with, the Company's
     bonus plans for senior level executives, and the grant and payment terms
     and the amount of any such bonuses shall be determined by the Compensation
     Committee.

          (b)  If you are then employed by the Company on a full-time basis, on
     or about January 1, 2005, the Company will make a lump sum payment to you
     in the amount of $200,000.

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     4.   EQUITY COMPENSATION.

          (a)  On July 15, 2004, the Company granted to you an option to
     purchase 15,625 shares of the common stock of the Company upon the terms
     and conditions set forth in the Company's 2001 Equity Incentive Plan (the
     "Plan") and that certain Employee Option Grant Agreement entered into
     between the Company and you as of July 15, 2004 (the "Option Agreement").
     The Option Agreement will be amended on or after the date hereof to provide
     that (i) in the event of a Change in Control of the Company (as defined in
     the Plan but EXCLUDING an initial public offering of the Company's common
     stock (the "IPO")), on the date of, and immediately prior to, the
     consummation of such Change in Control, one-half (1/2) of the unvested
     portion of such option shall vest and become exercisable, and the balance
     of the unvested shares subject to such option shall continue to vest
     ratably as provided in the Option Agreement, and (ii) if your employment is
     terminated by the Company without Cause (as defined below) and such
     termination is in connection with, and within 18 months after, a Change in
     Control, all of the unvested shares subject to such option shall fully vest
     on the later of (A) your termination of employment with the Company, and
     (B) the consummation of such Change in Control.

          (b)  Effectively promptly after the closing of the IPO, the Company
     will further grant to you an option to purchase 4,000 shares of the
     Company's common stock upon the terms and conditions of the Plan and its
     then-current form of Employee Option Grant Agreement. The exercise price
     for such grant shall be equal to the per-share IPO price. The option will
     vest subject to the terms and conditions set forth in the Plan and the
     then-current form of Employee Option Grant Agreement; PROVIDED, that in the
     event of a Change in Control of the Company (as defined in the Plan but
     EXCLUDING the IPO), on the date of, and immediately prior to, the
     consummation of such Change in Control, one-half (1/2) of the unvested
     portion of such option shall vest and become exercisable, and the balance
     of the unvested shares subject to such option shall continue to vest
     ratably as provided in the then-current form of the Employee Option Grant
     Agreement; PROVIDED, HOWEVER, that if your employment is terminated by the
     Company without Cause and such termination is in connection with, and
     within 18 months after, a Change in Control, all of the unvested shares
     subject to such option shall fully vest on the later of (i) your
     termination of employment with the Company, and (ii) the consummation of
     such Change in Control.

          (c)  Pursuant to a Restricted Stock Agreement substantially in the
     form attached hereto as EXHIBIT A, the Company will grant to you 8,125
     shares of common stock of the Company which are subject to certain
     contractual restrictions as set forth therein.

     5.   EMPLOYEE BENEFITS. During the term of your employment, you will be
entitled to participate in all employee welfare benefit plans of the Company
applicable to senior level executives (including, without limitation,
participation in any medical insurance and 401(k) plans generally maintained by
the Company from time to time). In addition, during the term of your employment,
you will be entitled to three (3) weeks' paid vacation per year. Further, you
shall be entitled to reimbursement for expenses incurred by you in the ordinary
course of the

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Company's business (subject to the Company's policies with respect to reporting
and documentation of such expenses).

     6.   TERMINATION AND SEVERANCE.

          (a)  During the term of employment hereunder, your employment may be
     terminated as follows:

               (i)    At any time upon prior written notice by the Company for
                      any reason other than Cause (as defined below) or for no
                      reason ("Termination Without Cause").

               (ii)   At any time upon three (3) months' prior written notice by
                      you for any reason other than Good Reason (as defined
                      below) or for no reason.

               (iii)  Automatically in the event of (A) your death or (B) your
                      inability to perform the essential duties,
                      responsibilities and functions of your position with the
                      Company as a result of any mental or physical incapacity,
                      even with reasonable accommodations for such disability or
                      incapacity provided by the Company, which inability lasts
                      (or is likely to last, based on competent medical evidence
                      presented to the Board) for a continuous period of six (6)
                      months or longer. The reasoned and good faith judgment of
                      the Board as to your mental or physical inability to
                      perform shall be final so long as such judgment is based
                      on competent medical evidence presented to the Board by
                      you and by any physician or group of physicians engaged by
                      you or the Board to advise the Board on such matters.

               (iv)   Immediately upon written notice by the Company if such
                      termination is for Cause ("Termination for Cause").

               (v)    Immediately upon written notice by you if such termination
                      is for Good Reason.

               (vi)   At any time by mutual written agreement between you and
                      the Company.

          (b)  Upon termination of your employment hereunder for any reason, all
     obligations of the Company shall cease upon such termination, except the
     Company's obligations to (i) pay the compensation set forth in Section 2
     hereof through the date of such termination, (ii) provide the benefits set
     forth in Section 5 hereof through the date of such termination and to
     comply with all state and federal laws and regulations applying to such
     benefits and (iii) pay the severance benefits, if applicable, to you
     pursuant to the terms and conditions set forth in Section 6(c) below. In
     the event that your employment is terminated by you without Good Reason or
     as a result of a Termination for Cause by

                                        3
<Page>

     the Company, you shall not be entitled to any bonus compensation in respect
     of the calendar year of your termination.

          (c)  In the event that your employment is terminated for Good Reason
     or as a result of a Termination Without Cause, you shall be entitled to
     receive an amount equal to twelve (12) months' severance pay at the monthly
     rate of your then-current Base Salary, payable in twelve (12) equal monthly
     installments following such termination, unless increased pursuant to the
     terms of Section 6(f) below, if and only if (i) you have executed and
     delivered to the Company a mutual general release of all claims against
     you, on the one hand, and the Company and its directors, officers and
     affiliates, on the other hand, which general release shall be in the form
     of EXHIBIT B attached hereto (with such modifications as may be necessary
     to comply with then-existing legal requirements), and (ii) subsequent to
     such termination, you shall not have (A) revoked or breached the provisions
     of such general release or breached or otherwise failed to comply with the
     provisions of Sections 7, 8 or 9 of this letter agreement, or (B) applied
     for unemployment compensation chargeable to the Company during such
     severance period.

          (d)  For purposes hereof, the term "Cause" means the following: (i)
     the commission of fraud, theft or embezzlement by you in connection with
     your duties to the Company or any of its customers or other material
     business relations; (ii) your conviction of (or entry of a plea of guilty
     or NOLO CONTENDERE to) a felony (other than minor traffic violations) (A)
     in connection with your duties to the Company or any of its customers or
     other material business relations, or (B) that materially and adversely
     effects your ability to continue in your position and fulfill your duties
     to the Company under applicable laws and regulations; (iii) your
     mismanagement demonstrably injurious to the Company, which is not cured
     within thirty (30) days after a written demand is delivered to you by the
     Board which identifies the grounds therefor; or (iv) any breach by you of
     the provisions of this letter agreement (including any breach by you of the
     provisions set forth in Sections 7, 8 or 9 hereof) or any other breach of
     any other agreement between or among you and the Company, in either event
     which breach has not been cured within thirty (30) days after a written
     demand is delivered to you by the Board which identifies the grounds
     therefor. Any disagreement concerning whether there has been "Cause" for
     termination will be resolved by the Board in its sole discretion acting in
     good faith after providing you an opportunity to address the Board at a
     full meeting thereof regarding whether or not there has been "Cause" for
     termination.

          (e)  For purposes hereof, the term "Good Reason" means your
     termination of employment with the Company as a result of the failure of
     the Company to comply in any material respect with any of its obligations
     hereunder or under any other agreements with you which remains uncured for
     a period of thirty (30) days following your written notice to the Company
     of such failure.

          (f)  In the event your employment with the Company is terminated for
     any reason, the Company shall have the option to elect in writing within
     sixty (60) days after the date of termination to pay you, in equal monthly
     installments, an additional amount equal to your then-current Base Salary
     for up to twenty-four (24) additional months following the Noncompetition
     Period, with any such additional period being referred to

                                        4
<Page>

     herein as the "Additional Restriction Period" (which amount shall be in
     addition to any other amounts payable to you under Section 6(c) hereof). If
     the Company makes such election then the restrictions contained in Sections
     8(a) and (b) hereof shall commence on the date of such termination and
     extend for the Additional Restriction Period. In the event the Company
     fails to make such election in the manner and during the time period set
     forth above, then the Company shall be deemed to have waived its rights to
     make an election under this Section 6(f).

     7.   CONFIDENTIALITY.

          (a)  You will not at any time during, or after termination of, your
     employment with the Company disclose to anyone or make use of, directly or
     indirectly, any Confidential Information (as defined below). All records of
     every nature and description relating to the Company's business during your
     employment, whether or not prepared by you, shall be and remain the
     property of the Company. All records of every nature and description
     relating to the Company's business during your employment shall be left
     with or delivered to the Company upon termination of your employment.

          (b)  For purposes of this letter agreement, "Confidential Information"
     means all information of a confidential or proprietary nature (whether or
     not specifically labeled or identified as "confidential"), in any form or
     medium, that relates to the Company or its subsidiaries or their business
     relations and their respective business activities and includes, without
     limitation, the following: (i) internal business information (including
     historical and projected financial information and budgets and information
     relating to strategic and staffing plans and practices, business, training,
     marketing, promotional and sales plans and practices, cost, rate and
     pricing structures and accounting and business methods); (ii) identities
     and individual requirements of, and specific contractual arrangements with,
     the Company's and its subsidiaries' customers, employees, independent
     contractors, clearing agencies, joint venture partners and other business
     relations and their confidential information; (iii) trade secrets,
     know-how, compilations of data and analyses, techniques, systems, formulae,
     research, records, reports, manuals, documentation, models, data and data
     bases relating thereto; (iv) inventions, innovations, improvements,
     developments, methods, designs, analyses, drawings, reports and all similar
     or related information (whether or not patentable); and (v) information
     related to any and all intellectual and proprietary property and rights and
     rights in Confidential Information of every kind and description anywhere
     in the world, including all (A) patents, patent applications, patent
     disclosures and inventions, (B) internet domain names, trademarks, service
     marks, trade dress, trade names, logos and corporate names and
     registrations and applications for registration thereof together with all
     of the goodwill associated therewith, (C) copyrights (registered or
     unregistered) and copyrightable works and registrations and applications
     for registration thereof, (D) mask works and registrations and applications
     for registration thereof, (E) computer software, data, data bases and
     documentation thereof, (F) trade secrets and other Confidential Information
     (including ideas, formulas, compositions, inventions (whether patentable or
     unpatentable and whether or not reduced to practice), know-how,
     manufacturing and production processes and techniques, research and
     development information, drawings, specifications, designs, plans,
     proposals, technical data, copyrightable works, financial

                                        5
<Page>

     and marketing plans and customer and supplier lists and information), (G)
     other intellectual property rights and (H) copies and tangible embodiments
     thereof (in whatever form or medium).

          (c)  Notwithstanding the provisions of this Section 7, information
     shall not be deemed "Confidential Information" for purposes hereof if such
     information is (i) in the public domain (other than as a result of a breach
     of this Agreement by you), (ii) approved for release by the Company, (iii)
     lawfully obtained by you after termination of your employment with the
     Company from third parties (other than the Company or any of its affiliates
     or any of their respective employees, directors or representatives) on a
     nonconfidential basis who, to your knowledge, are not prohibited from
     disclosing such information to you by a legal, contractual or fiduciary
     obligation to the Company or any of its affiliates, or (iv) actually known
     by you prior to the commencement of the discussions between the Company and
     you which resulted in your employment with the Company as evidenced by
     written records maintained by you.

     8.   NONCOMPETITION; NONSOLICITATION.

          (a)  You acknowledge that (i) you are one of the Company's key
     employees and that you are and will become familiar with the Company's
     trade secrets and with other confidential information concerning the
     Company, including the Company's (A) inventions, technology and research
     and development, (B) customers and vendors and customer and vendor lists,
     (C) products and services (including those under development) and related
     costs and pricing structures, (D) accounting and business methods and
     practices, and (E) similar and related confidential information and trade
     secrets; (ii) your services have been and shall continue to be of special,
     unique and extraordinary value to the Company and that you have been and
     will be substantially responsible for the growth and development of the
     Company and the creation and preservation of the Company's goodwill; and
     (iii) the Company would be irreparably damaged (including a significant
     loss of goodwill) if you were to provide similar services to any person or
     entity competing with the Company or engaged in a similar business. Due to
     your access to the confidential proprietary information, customer
     information and customer relationships and uniqueness of your services to
     the Company and in consideration of the Company's agreements herein, you
     agree that for the term of your employment with the Company and a period of
     one (1) year after termination of your employment as provided hereunder
     (the "Noncompetition Period"), unless such one (1) year period is extended
     pursuant to the provisions of Section 6(f) above, you shall not directly or
     indirectly, either for yourself or for any other individual, corporation,
     partnership, joint venture or other entity, own any interest in, manage,
     control, participate in (whether as an officer, director, employee,
     partner, agent, representative or otherwise), consult with or render
     services for any entity that (in whole or in part) engages or proposes to
     engage in, or in any other manner engage, anywhere in the world, in the
     on-line securities industry for the retail, consumer customer base
     (including, for the avoidance of doubt and without limitation, the service
     of retail brokerage accounts through independent representatives) or any
     other business conducted by the Company or any of its subsidiaries during
     your employment term or proposed to be conducted by the Company or any of
     its subsidiaries within the six (6) month period prior to the

                                        6
<Page>

     termination of your employment; PROVIDED, HOWEVER, that nothing herein
     shall prohibit you from being a passive owner of not more than ten percent
     (10%) of the outstanding stock of any class of a corporation which is
     publicly traded so long as you do not have any active participation in the
     business of such corporation.

          (b)  During the Noncompetition Period, you shall not directly or
     indirectly (through any other individual, corporation, partnership, joint
     venture or other entity or otherwise) (i) induce or attempt to induce any
     employee of the Company or any of its subsidiaries to leave the employ of
     the Company or any of its subsidiaries, or in any way interfere with the
     relationship between the Company or any of its subsidiaries and any
     employee thereof, (ii) hire any person who was an employee of the Company
     or any of its subsidiaries at any time during the six (6) month period
     immediately prior to the date on which such hiring would take place, or
     (iii) call on, solicit or service any customer, supplier, licensee,
     licensor or other business relation of the Company or any of its
     subsidiaries in order to induce or attempt to induce such person to cease
     doing business with the Company or any of its subsidiaries, or in any way
     interfere with the relationship between any such customer, supplier,
     licensee or business relation and the Company or any of its subsidiaries.
     Each of you and the Company (on behalf of itself and its subsidiaries)
     mutually agree not to make any negative statements or communications about
     the other and, in the case of the Company, about any of its subsidiaries.

          (c)  If, at the time of enforcement of the covenants contained in this
     Section 8 (the "Restrictive Covenants"), a court shall hold that the
     duration, scope or area restrictions stated herein are unreasonable under
     circumstances then existing, you agree that the maximum duration, scope or
     area reasonable under such circumstances shall be substituted for the
     stated duration, scope or area and that the court shall be allowed and
     directed to revise the restrictions contained herein to cover the maximum
     period, scope and area permitted by law. You acknowledge that you have
     consulted with legal counsel regarding the Restrictive Covenants and, based
     on such consultation, have determined and hereby acknowledge that the
     Restrictive Covenants are reasonable in terms of duration, scope and area
     restrictions and are necessary to protect the goodwill of the Company's
     business and the on-line nature of the Company's business is such that it
     is not conducted with respect to geographical boundaries.

          (d)  If you breach, or threaten to commit a breach of, any of the
     Restrictive Covenants, the Company shall have the right and remedy to have
     the Restrictive Covenants specifically enforced by any court of competent
     jurisdiction, it being agreed that any breach or threatened breach of the
     Restrictive Covenants would cause irreparable injury to the Company and
     that money damages would not provide an adequate remedy to the Company.

          (e)  In the event of any breach or violation by you of any of the
     Restrictive Covenants, the time period of such covenant shall be tolled
     until such breach or violation is resolved.

     9.   THE COMPANY'S OWNERSHIP OF INTELLECTUAL PROPERTY.

                                        7
<Page>

          (a)  In the event that you, as part of your activities on behalf of
     the Company or any of its subsidiaries generate, author or contribute to
     (whether before or after the date of this letter agreement) any invention,
     design, new product or service development, device, product, method or
     process (whether or not patentable or reduced to practice or comprising
     Confidential Information), any copyrightable work (whether or not
     comprising Confidential Information) or any other form of Confidential
     Information relating directly or indirectly to the Company's or any of its
     subsidiaries' business as now or hereinafter conducted (the "Intellectual
     Property"), you acknowledge that such Intellectual Property is the
     exclusive property of the Company and hereby assign all right, title and
     interest in and to such Intellectual Property to the Company. Any
     copyrightable work prepared in whole or in part by you will be deemed "a
     work made for hire" under Section 201(b) of the 1976 Copyright Act, and the
     Company shall own all of the rights comprised in the copyright therein. You
     shall promptly and fully disclose to the Company all Intellectual Property
     not generally known to the Company through the ordinary course of operation
     of the business, and you shall cooperate with the Company to protect the
     Company's interests in and rights to such Intellectual Property (including,
     without limitation, providing reasonable assistance in securing patent
     protection and copyright registrations and executing all documents as
     reasonably requested by the Company, whether such requests occur prior to
     or after termination of your employment with the Company). The Company
     agrees to pay you for any reasonable costs, fees and expenses incurred by
     you for providing your assistance pursuant to this Section 9, including,
     but not limited to, any of your costs, expenses and your hourly fees if
     such assistance is provided after your termination for any reason.

          (b)  In accordance with Section 2872 of the Illinois Employee Patent
     Act, Ill. Rev. Stat. Chap. 140, Section 301 et seq. (1983), you are hereby
     advised that Section 9 of this Agreement regarding the Company's ownership
     of Intellectual Property does not apply to any invention for which no
     equipment, supplies, facilities or trade secret information of the Company
     was used and which was developed entirely on your own time, unless (i) the
     invention relates to the business of the Company or any of its subsidiaries
     or to the Company's or any of its subsidiaries actual or demonstrably
     anticipated research or development or (ii) the invention results from any
     work performed by you for or on behalf of the Company or any of its
     subsidiaries.

     10.  BINDING EFFECT. The terms hereof shall be binding upon and shall inure
to the benefit of you and the Company, the successors and assigns of the
Company, and the heirs, executors, administrators, legal representatives and
assigns of you, PROVIDED THAT your rights and obligations hereunder may not be
delegated or assigned.

     11.  ENTIRE AGREEMENT. This letter agreement shall supersede any former
oral agreement and any former written agreement heretofore executed relating
generally to your employment with the Company, and this letter agreement can
only be amended, altered or terminated and its provisions can only be waived by
an agreement in writing signed by you and the Company; PROVIDED, HOWEVER, that
this letter agreement shall not be deemed to supersede any restricted stock,
equity award or other agreement between the Company and you.

                                        8
<Page>

     12.  REPRESENTATIONS. You hereby represent and warrant to the Company that
(a) the execution, delivery and performance of this Agreement by you does not
and shall not conflict with, breach, violate or cause a default under any
contract, agreement, instrument, order, judgment or decree to which your are a
party or by which your are bound, (b) you are not a party to or bound by any
employment agreement, noncompete agreement or confidentiality agreement with any
person or entity other than the Company and/or its subsidiaries and (c) upon the
execution and delivery of this Agreement by the Company, this Agreement shall be
the valid and binding obligation of you, enforceable in accordance with its
terms. You hereby acknowledge and represent that you have consulted with
independent legal counsel (or that you have decided to forego the engagement of
such legal counsel) regarding your rights and obligations under this Agreement
and that you fully understand the terms and conditions contained herein.

     13.  COOPERATION. During the term of your employment and for a period of
two (2) years after termination of your employment for any reason, you shall
reasonably cooperate with the Company in (a) any internal investigation or any
administrative, regulatory or judicial proceeding (so long as such investigation
or proceeding is not adversarial in nature between you and the Company) or (b)
any dispute with a third party, as reasonably requested by the Company
(including, without limitation, being available to the Company upon reasonable
advance notice for interviews and factual investigations, appearing at the
Company's request to give testimony without requiring service of a subpoena or
other legal process, volunteering to the Company all pertinent information and
turning over to the Company all relevant documents which are or may come into
your possession, all at times and on schedules that are reasonably consistent
with your other activities and commitments). In the event the Company requires
your cooperation in accordance with this Section, the Company shall reimburse
you for all reasonable travel and other out-of-pocket expenses (including
lodging and meals) incurred by you in connection therewith promptly upon
submission of receipts therefor.

     14.  REMEDIES. In the event that you violate any of the provisions hereof,
you hereby acknowledge that the Company will suffer irreparable damages and will
be entitled to full injunctive relief or such other relief against you as may be
provided by law or in equity.

     15.  ENFORCEABILITY. This letter agreement shall be construed and enforced
under the laws of the State of Illinois without giving effect to the principles
of conflicts of laws thereof. If any provision of this letter agreement is held
invalid or unenforceable by operation of law or otherwise, such circumstances
shall not have the effect of rendering any of the other provisions of this
letter agreement invalid or unenforceable.

                            [SIGNATURE PAGE FOLLOWS]

                                        9
<Page>

                 [SIGNATURE PAGE TO EMPLOYMENT LETTER AGREEMENT]

     By signing below, the Company agrees to all of the terms and conditions of
this letter agreement. Please indicate your acceptance of these terms and
conditions by signing each enclosed copy of this letter agreement where
indicated below, and return an originally-executed copy of this letter agreement
to the undersigned.

                                      Sincerely yours,

                                      optionsXpress Holdings, Inc.

                                      By:   /s/ DAVID KALT
                                         ---------------------------------------
                                            David Kalt, Chief Executive Officer

ACCEPTED AND AGREED as of
this 15th day of July, 2004.

 /s/ DAVID FISHER
------------------------------
David Fisher

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