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                                                                    Exhibit 10.2

                               OPTIONSXPRESS, INC.
                             STOCKHOLDERS AGREEMENT

          THIS STOCKHOLDERS AGREEMENT (this "AGREEMENT") is made and entered
into as of January 15, 2004 by and among optionsXpress, Inc., a Delaware
corporation (the "COMPANY"), each of the Persons listed on the SCHEDULE OF
INVESTORS attached hereto (each, an "INVESTOR" and collectively, the
"INVESTORS") and each of the Persons listed on the SCHEDULE OF OTHER
STOCKHOLDERS attached hereto (each, an "OTHER STOCKHOLDER" and collectively, the
"OTHER STOCKHOLDERS"). The Investors and the Other Stockholders are collectively
referred to herein as the "STOCKHOLDERS" and individually as a "STOCKHOLDER."
Except as otherwise provided herein, capitalized terms used herein are defined
in paragraph 8 hereof.

          WHEREAS, the Investors shall purchase shares of the Company's Series A
Convertible Preferred Stock, par value $.0001 per share (the "SERIES A
PREFERRED"), pursuant to that certain Stock Purchase and Recapitalization
Agreement, dated as of December 17, 2003, by and among the Company and the
Investors and the other Persons named therein (as the same may be amended or
modified from time to time in accordance with its terms, the "PURCHASE
AGREEMENT");

          WHEREAS, the Other Stockholders own shares of the Company's
outstanding Common Stock, par value $.0001 per share (the "COMMON STOCK");

          WHEREAS, certain of the Other Stockholders and the Company are parties
to an Amended and Restated Investor Rights Agreement dated December 19, 2001
(the "INVESTOR RIGHTS AGREEMENT");

          WHEREAS, certain of the Other Stockholders and the Company are parties
to separate Amended and Restated Restricted Stock Agreements dated as of the
date hereof (the "RESTRICTED STOCK AGREEMENTS");

          WHEREAS, certain of the Other Stockholders and the Company are parties
to separate Option Grant Agreements dated as of various dates (the "OPTION GRANT
AGREEMENTS");

          WHEREAS, the Company and the Stockholders desire to enter into this
Agreement for the purposes, among others, of (i) establishing the composition of
the Company's board of directors (the "BOARD"), (ii) assuring continuity in the
management and ownership of the Company and (iii) limiting the manner and terms
by which the Company's capital stock may be transferred; and

          WHEREAS, the execution and delivery of this Agreement is a condition
to the Closing (as defined in the Purchase Agreement) under the Purchase
Agreement.

          NOW, THEREFORE, in consideration of the mutual covenants contained
herein and other good and valuable consideration, the receipt and sufficiency of
which are hereby acknowledged, the parties to this Agreement hereby agree as
follows:

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          1.   BOARD OF DIRECTORS.

          (a)  From and after the Closing and until the provisions of this
paragraph 1 cease to be effective, each holder of Stockholder Shares shall vote
all of his, her or its Stockholder Shares which are voting shares and any other
voting securities of the Company over which such holder has voting control and
shall take all other necessary or desirable actions within his, her or its
control (whether in his, her or its capacity as a stockholder, director, member
of a board committee or officer of the Company or otherwise, and including
attendance at meetings in person or by proxy for purposes of obtaining a quorum
and execution of written consents in lieu of meetings), and the Company shall
take all necessary or desirable actions within its control (including calling
special board and stockholder meetings), so that:

               (i)    the authorized number of directors on the Board shall be
     established and maintained at five (5) directors;

               (ii)   the following persons shall be elected to the Board:

               (A)    so long as the Investors who are original signatories
          hereto and/or their affiliated investment funds hold in the aggregate
          at least 25% of the Series A Preferred issued to the Investors as of
          the date hereof, one (1) representative designated by the Investors
          that hold a majority of the Stockholder Shares held by all of the
          Investors (the "INVESTOR DIRECTOR"), with Christopher J. Dean serving
          as the Investor Director immediately following the Closing (and with
          it being understood that such Investor Director shall be elected by
          the holders of a majority of the outstanding Series A Preferred
          pursuant to Section 5A of Part D of Article IV of the Company's
          Certificate of Incorporation for so long as any Series A Preferred
          remains outstanding);

               (B)    three (3) representatives elected by the holders of the
          Company's outstanding Common Stock (voting together as a single class
          with any of the Existing Preferred that remains outstanding following
          the Closing on an as-if converted basis) in accordance with applicable
          corporate law and the Company's Certificate of Incorporation and
          Bylaws (the "OTHER STOCKHOLDER DIRECTORS"), with James Gray, Ned
          Bennett and David Kalt serving as the Other Stockholder Directors
          immediately following the Closing; PROVIDED THAT, in the event that,
          and only for so long as, either (1) the Company's Equity Value is less
          than $180,000,000 or (2) the Designated Other Stockholder Group owns,
          in the aggregate, less than 51% of the Company's outstanding Common
          Stock (including any Common Stock issuable upon conversion of any of
          the Existing Preferred that remains outstanding following the
          Closing), then the Other Stockholder Directors shall be elected by
          (and shall be subject to removal by) the holders of the Company's
          outstanding Common Stock and Existing Preferred (to the extent that
          any Existing Preferred remains outstanding following the Closing) and
          Series A Preferred (voting together with the Company's outstanding
          Common Stock as a single class on an as-if-converted basis) in
          accordance with applicable corporate law and the Company's Certificate
          of Incorporation and Bylaws; and

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               (C)    so long as the Investors who are original signatories
          hereto and/or their affiliated investment funds hold in the aggregate
          at least 25% of the Series A Preferred issued to the Investors as of
          the date hereof, one (1) representative elected by the holders of the
          Company's outstanding Common Stock, any of the Existing Preferred that
          remains outstanding following the Closing and Series A Preferred
          (voting together with the Company's outstanding Common Stock as a
          single class on an as-if-converted basis) in accordance with
          applicable corporate law and the Company's Certificate of
          Incorporation and Bylaws, so long as such representative is approved
          by the Investors that hold a majority of the Stockholder Shares held
          by all of the Investors (which approval shall not be unreasonably
          withheld or delayed so long as such representative satisfies the
          requirements set forth below); PROVIDED THAT such representative shall
          be qualified (including by virtue of relevant business and industry
          experience) and independent and shall not be a member of the Company's
          management or an employee or officer of the Company or any of its
          Subsidiaries and shall not be a member of or otherwise affiliated with
          (from a business perspective or otherwise) the Designated Other
          Stockholder Group or the Gray Family Group (the "OUTSIDE DIRECTOR"),
          and with such Outside Director being so designated and approved as
          provided herein and elected to the Board as soon as practicable after
          the Closing;

               (iii)  the composition of the board of directors or equivalent
     body of each of the Company's Subsidiaries (a "SUB BOARD") shall be
     proportionately equivalent to that of the Board;

               (iv)   subject to subparagraph (ii)(B) above and
     paragraph 1(a)(v) below, any director of the Company may be removed from
     the Board or a Sub Board in the manner allowed by law and the Company's or
     such Subsidiary's Certificate of Incorporation and Bylaws or similar
     governing documents; PROVIDED THAT, (A) with respect to the Investor
     Director, such removal (with or without cause) shall only be upon the
     written request of the Investors that hold a majority of the Stockholder
     Shares held by all of the Investors and for no other reason and (B) with
     respect to any Outside Director, such removal (with or without cause) shall
     also require the written approval of the Investors that hold a majority of
     the Stockholder Shares held by all of the Investors; and

               (v)    in the event that any representative designated hereunder
     for any reason ceases to serve as a member of the Board or any Sub Board
     during his or her term of office, the resulting vacancy on the Board or Sub
     Board shall be filled by (A) with respect to the representative designated
     pursuant to subparagraph (ii)(A) above, a representative designated by the
     Investors that hold a majority of the Stockholder Shares held by all of the
     Investors, (B) with respect to a representative elected pursuant to
     subparagraph (ii)(B) above, a representative elected as provided in
     subparagraph (ii)(B) above, and (C) with respect to a representative
     elected pursuant to subparagraph (ii)(C) above, a representative elected
     and approved as provided in subparagraph (ii)(C) above, who satisfies the
     other requirements set forth in subparagraph (ii)(C) above.

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          (b)  Subject to subparagraphs (i) and (ii) below, any committees
established by the Board or a Sub Board shall include the Investor Director, the
Outside Director and at least one Other Stockholder Director.

               (i)    A Compensation Committee of the Board comprised of three
     (3) members shall be established promptly following the Closing and shall
     include the Investor Director, one Other Stockholder Director and the
     Outside Director. The Compensation Committee's authority and duties shall
     include (1) determining the compensation (including salary, bonuses and
     other forms of compensation) to be paid to each of the Company's executives
     and key employees and, subject to approval by the Board, directors and (2)
     the administration of (and exercise of any rights or powers under) the
     Company's Equity Incentive Plans.

               (ii)   An Audit Committee of the Board comprised of three (3)
     members shall be established promptly following the Closing and shall
     include the Investor Director, one Other Stockholder Director and the
     Outside Director. The Audit Committee's authority and duties shall be as
     set forth in the Board's enabling resolutions adopted in connection with
     the establishment of such committee.

          (c)  The Company shall pay the reasonable out-of-pocket expenses
(including travel expenses) incurred by each director in connection with
attending the meetings of the Board, any Sub Board and any committee thereof and
each non-management director (including the Investor Director) shall receive the
same remuneration (of whatever type) for serving as a director (if any);
PROVIDED THAT compensation received by James Gray pursuant to that certain
Employment Letter Agreement with the Company, dated as of the date hereof, or
otherwise payable to Mr. Gray with the approval of the Compensation Committee,
shall not be deemed to constitute remuneration received by a non-management
director for purposes hereof. The Company shall use its reasonable efforts to
maintain reasonable directors and officers indemnity insurance coverage in
effect at all times (subject to appropriate cost considerations) and the
Company's Certificate of Incorporation and Bylaws shall at all times provide for
indemnification and exculpation of directors to the fullest extent permitted
under applicable law.

          (d)  The Board shall have regularly scheduled meetings no less than
one (1) time in each fiscal quarter of each calendar year.

          (e)  The provisions of this paragraph 1 shall terminate automatically
and shall be of no further force and effect upon the consummation of a Qualified
Public Offering or a Sale of the Company.

          2.   REPRESENTATIONS AND WARRANTIES; AGREEMENTS. Each Stockholder
represents and warrants as of the date hereof that (i) this Agreement has been
duly authorized, executed and delivered by such Stockholder and constitutes the
valid and binding obligation of such Stockholder, enforceable in accordance with
its terms, and (ii) such Stockholder has not granted and is not a party to any
proxy, voting trust or other agreement which is inconsistent with, conflicts
with or violates any provision of this Agreement. No holder of Stockholder
Shares shall grant any proxy or become party to any voting trust or other
agreement which is inconsistent with, conflicts with or violates any provision
of this Agreement.

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          3.   CERTAIN TRANSFER RESTRICTIONS.

          (a)  No Other Stockholder shall sell, transfer, assign, pledge or
otherwise dispose of (whether with or without consideration and whether
voluntarily or involuntarily or by operation of law or otherwise) any interest
in any Stockholder Shares, (a "TRANSFER"), except pursuant to a Public Sale or a
Sale of the Company (an "EXEMPT TRANSFER"), or a sale of Stockholder Shares to
the Company pursuant to the terms of the Restricted Stock Agreement (but subject
to the provisions of paragraph 3(f) below), or the provisions of this paragraph
3. Prior to making any Transfer (which for purposes of this paragraph 3 shall
include any Transfer by any Other Stockholder pursuant to and otherwise
permitted by any of the Restricted Stock Agreements, the Investor Rights
Agreement and/or any Option Grant Agreement to which such Other Stockholder is a
party) other than an Exempt Transfer, the Other Stockholder transferring any
Stockholder Shares (a "TRANSFERRING STOCKHOLDER") shall deliver a written notice
(a "SALE NOTICE") to the Company, the Investors and the Designated Other
Stockholders. The Sale Notice shall disclose in reasonable detail the identity
of the prospective transferee(s), the number of Stockholder Shares to be
transferred and the terms and conditions of the proposed Transfer. In no event
shall any Transfer (other than an Exempt Transfer) of Stockholder Shares
pursuant to this paragraph 3 be made by any Other Stockholder for any
consideration other than cash payable upon consummation of such Transfer or in
installments over time. No Other Stockholder shall consummate any Transfer until
30 days after the Sale Notice has been given to the Company and the Investors
and the Designated Other Stockholders (the "ELECTION PERIOD"), unless the
parties to the Transfer have been finally determined pursuant to this paragraph
3 prior to the expiration of such 30-day period. The date of the first to occur
of such events is referred to herein as the "AUTHORIZATION DATE."

          (b)  The Company may elect to purchase all or any portion of the
Transferring Stockholder's Stockholder Shares to be transferred upon the same
terms and conditions as those set forth in the Sale Notice by delivering a
written notice of such election to such Transferring Stockholder, the Investors
and the Designated Other Stockholders within 15 days after the Sale Notice has
been delivered to the Company. If the Company has not elected to purchase all of
such Transferring Stockholder's Stockholder Shares to be transferred, each of
the Investors and the Designated Other Stockholders may elect to purchase all or
any portion of the remaining Stockholder Shares to be transferred upon the same
terms and conditions as those set forth in the Sale Notice by delivering written
notice of such election to the Transferring Stockholder within 20 days after the
Sale Notice has been given to the Investors and the Designated Other
Stockholders. If more than one Investor or Designated Other Stockholder elects
to purchase such Stockholder Shares, the Stockholder Shares to be sold to such
Investors and/or Designated Other Stockholders shall be allocated (i) among the
Investors pro rata according to the number of Stockholder Shares owned by each
such Investor in an aggregate amount equal to the lesser of (A) one-third of the
aggregate Stockholder Shares to be transferred, and (B) the collective
percentage ownership of outstanding Common Stock (including shares of Common
Stock issuable upon conversion of the Series A Preferred) of all Investors, and
(ii) among the Designated Other Stockholders pro rata according to the number of
Stockholder Shares owned by each such Designated Other Stockholder in an amount
equal to all of the Stockholder Shares to be transferred other than those
allocated to the Investors pursuant to clause (i) immediately above. If the
Company, the Investors and the Designated Other Stockholders have not elected to
purchase all of such Transferring Stockholder's Stockholder Shares specified in
the Sale Notice,

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such Transferring Stockholder may Transfer the Stockholder Shares specified in
the Sale Notice for which no purchase election has been made at a price and on
terms no more favorable to the transferee(s) thereof than specified in the Sale
Notice (subject to the provisions of paragraph 3(c) below) during the 60-day
period immediately following the Authorization Date. Any Transferring
Stockholder's Stockholder Shares not transferred within such 60-day period shall
be subject to the provisions of this paragraph 3(b) upon subsequent Transfer. If
any of the Company, the Investors or the Designated Other Stockholders have
elected to purchase any Stockholder Shares hereunder, the Transfer of such
Stockholder Shares shall be consummated as soon as practical after the delivery
of the election notice(s) to the Transferring Stockholder, but in any event
within 15 days after the expiration of the Election Period. The Investors may
assign all or any portion of their repurchase rights under this paragraph 3(b)
to one or more of their affiliated investment funds.

          (c)  Notwithstanding anything to the contrary herein, the Investors
may elect to participate in any contemplated Transfer by delivering written
notice to such Transferring Stockholder and the Company within 30 days after
receipt by such Investor of the Sale Notice. If any Investors have elected to
participate in such sale, the Transferring Stockholder and the electing
Investors shall be entitled to sell in the contemplated sale (including any sale
to the Company or any other Stockholders pursuant to paragraph 3(b) above) at
the same price and on the same terms, a number of Stockholder Shares equal to
the product of (i) the quotient determined by dividing the percentage of
Stockholder Shares owned by such Person by the aggregate percentage of
Stockholder Shares owned by the Transferring Stockholder and all electing
Investors and (ii) the number of Stockholder Shares to be sold in the
contemplated sale.

     For example, if the Sale Notice contemplated a sale of 100
     Stockholder Shares, and if the Transferring Stockholder was at
     such time the owner of 30% of all Stockholder Shares and if one
     Investor elected to participate and such Investor owned 20% of
     all Stockholder Shares, the Transferring Stockholder would be
     entitled to sell 60 Stockholder Shares (30% DIVIDED BY 50% x 100
     Stockholder Shares) and the Investor would be entitled to sell 40
     Stockholder Shares (20% DIVIDED BY 50% x 100 Stockholder Shares).

The Transferring Stockholder shall use his, her or its best efforts to obtain
the agreement of the prospective transferee(s) to the participation of the
Investors in the contemplated Transfer and shall not Transfer any Stockholder
Shares to the prospective transferee(s) if such transferee(s) refuses to allow
the participation of the Investors.

          (d)  The restrictions contained in this paragraph 3 shall not apply
with respect to (i) any pledge by any Other Stockholder of up to 30% of the
value of such Other Stockholder's Stockholder Shares (as determined by the Board
at the time of such loan transaction) in support of a bona fide loan transaction
for such Other Stockholder's benefit (E.G., an Other Stockholder with
Stockholder Shares valued at $10,000,000 at the time of such loan transaction
may pledge all of such shares as collateral security for a loan of up to
$3,000,000) so long as, as a condition to any such pledge, the third party
lender agrees to grant the Company, the Investors and the Designated Other
Stockholders the right (in accordance with the provisions of paragraph 3(b)
above) to repurchase any such Stockholder Shares upon any default or foreclosure
in respect thereof by the applicable lender on terms and conditions satisfactory
to the

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Board (including the Investor Director), (ii) any Transfer (by way of in-kind
distribution) of Stockholder Shares by any Other Stockholder that is any entity
to the equity holder(s) of such Other Stockholder pro rata in accordance with
such other equity holders(s)' ownership interest in such Other Stockholder, or
(iii) any Transfer of Stockholder Shares by any Other Stockholder that is an
individual or trust (A) pursuant to applicable laws of descent and distribution
or (B) among such Other Stockholder's Family Group (collectively referred to
herein, for purposes of clauses (i), (ii) and (iii), as "PERMITTED
TRANSFEREES"); PROVIDED THAT such restrictions shall continue to be applicable
to the Stockholder Shares after any such Transfer and the transferees of such
Stockholder Shares shall agree in writing to be bound by the provisions of this
Agreement affecting the Stockholder Shares so transferred as a condition
precedent to any such Transfer. For purposes of this Agreement, "FAMILY GROUP"
means an individual's spouse, ancestors and descendants (whether natural or
adopted), the beneficiaries of any trust which is a Stockholder as of the date
hereof, or any partnership, limited liability company or trust established
principally for the benefit of such individual and/or such individual's spouse,
ancestors and/or descendants or any not-for-profit charitable entity.
Notwithstanding the foregoing, no party hereto shall avoid the provisions of
this Agreement by making one or more transfers to one or more Permitted
Transferees and then disposing of all or any portion of such party's interest in
any such Permitted Transferee, other than to a Permitted Transferee as provided
above or as a consequence of the death of the transferor.

          (e)  The restrictions set forth in this paragraph 3 shall continue
with respect to each Stockholder Share following any Transfer thereof (other
than an Exempt Transfer or a Transfer to an Investor (or any of its affiliated
investment funds) pursuant to subparagraph 3(b) above; PROVIDED THAT all such
restrictions shall terminate upon the consummation of a Qualified Public
Offering or a Sale of the Company.

          (f)  Notwithstanding any provision to the contrary herein, (i) the
restrictions on Transfer of Common Stock contained in the Investor Rights
Agreement, the Restricted Stock Agreements and the Option Grant Agreements, and
the terms of payment for such Common Stock or other securities upon exercise of
any repurchase rights therefor contained in such agreements, shall continue in
full force and effect, and (ii) the Company shall not approve or consent to any
Transfer of any Stockholder Shares by any Other Stockholder pursuant to the
terms of the Investor Rights Agreement, the Restricted Stock Agreements or the
Option Grant Agreements unless such Transfer shall thereafter be subject to the
provisions of this paragraph 3. In addition, if and to the extent that the
Company shall not exercise in full any of its repurchase (or buy-back) rights in
the Investor Rights Agreement, the Restricted Stock Agreements or the Option
Grant Agreements, the Company and the other party(ies) thereto shall permit the
Investors and the Designated Other Stockholders (in accordance with the
provisions of paragraph 3(b) above) to repurchase any Common Stock (or other
securities) not so purchased by the Company.

          4.   HOLDBACK AGREEMENT. No Other Stockholder shall effect any public
sale or distribution (including sales pursuant to Rule 144 under the Securities
Act) of any Stockholder Shares or of any other capital stock or equity
securities of the Company, or any securities convertible into or exchangeable or
exercisable for such stock or securities, during the seven (7) days prior to and
the 180-day period beginning on the effective date of the Company's initial
Public Offering or during the seven (7) days prior to and the 90-day period
beginning on the

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effective date of any underwritten Demand Registration or Piggyback Registration
(each as defined in the Registration Agreement), except as part of such
underwritten registration if otherwise permitted in the Registration Agreement,
unless the underwriters managing the registration otherwise agree in writing.

          5.   TRANSFERS; FUTURE SALES. Prior to any Stockholder Transferring
any Stockholder Shares (other than pursuant to an Exempt Transfer) to any Person
and prior to the Company issuing any Common Stock (other than pursuant to an
initial Public Offering) or any options or other rights to acquire Common Stock
or any securities convertible into or exchangeable for such Common Stock to any
Person, such Stockholder or the Company, as the case may be, shall cause the
prospective transferee to be bound by this Agreement and to execute and deliver
to the Company and the other Stockholders a counterpart of this Agreement.
Transferees of Stockholder Shares held by Investors (other than the Other
Stockholders or their Permitted Transferees, all of whom shall be deemed to be
Other Stockholders hereunder) shall be deemed to be Investors hereunder.
Transferees of Stockholder Shares held by Other Stockholders (other than the
Investors or their affiliates, all of whom shall be deemed to be Investors
hereunder) and transferees of Common Stock (or options or other rights to
acquire Common Stock or securities convertible into or exchangeable for such
Common Stock) issued by the Company (other than the Investors and/or their
designees, all of whom shall be deemed to be Investors hereunder) shall be
deemed to be Other Stockholders hereunder.

          6.   LEGEND. Each certificate evidencing Stockholder Shares and each
certificate issued in exchange for or upon the Transfer of any Stockholder
Shares shall be stamped or otherwise imprinted with a legend in substantially
the following form:

          "The transfer of the securities represented by this
          certificate is subject to a Stockholders Agreement dated as
          of [________], among the issuer of such securities (the
          "Company") and certain of the Company's stockholders, as the
          same may be amended or modified from time to time. A copy of
          such Stockholders Agreement shall be furnished without
          charge by the Company to the holder hereof upon written
          request."

The Company shall imprint such legend on certificates evidencing Stockholder
Shares outstanding as of the date hereof.

          7.   FIRST REFUSAL RIGHTS.

          (a)  Except for issuances of Common Stock (i) pursuant to an Equity
Incentive Plan, (ii) upon the conversion of the Series A Preferred, (iii)
pursuant to the exercise or conversion of any warrants or convertible securities
issued after the date hereof in compliance with the provisions of this paragraph
7 so long as the issuance of Common Stock upon the exercise or conversion
thereof is in accordance with the original terms of such warrants or convertible
securities, (iv) as consideration in connection with the acquisition of another
company or business, (v) pursuant to a Public Offering, or (vi) pursuant to an
Option Adjustment Dividend, if the Company authorizes the issuance or sale of
any shares of

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Common Stock or any securities (including debt securities) containing options or
rights to acquire any shares of Common Stock (other than as a dividend on the
outstanding shares of Common Stock) or any securities exchangeable for or
convertible into Common Stock (collectively, "SECURITIES"), the Company shall
first offer to sell to each Investor, pro rata based upon such Investor's
ownership of Common Stock (including shares of Common Stock issuable upon
conversion of the Series A Preferred), a portion of such Securities equal to the
lesser of (A) one-third of the aggregate Securities to be issued, and (B) the
collective percentage ownership of outstanding Common Stock (including shares of
Common Stock issuable upon conversion of the Series A Preferred) of all
Investors, and shall offer to sell to each Designated Other Stockholder, so long
as such Designated Other Stockholder holds at least 50% of the Stockholder
Shares held by such Designated Other Stockholder as of the date hereof, pro rata
based upon such Designated Other Stockholder's ownership of Common Stock
(including shares of Common Stock issuable upon conversion of the Existing
Preferred), all of the Securities to be issued other than those to be offered to
the Investors pursuant to clause (A) immediately above. Each Investor and
Designated Other Stockholder shall be entitled to purchase all or any portion of
its allotment of such Securities at the most favorable price and on the most
favorable terms as such Securities are to be offered to any other Persons;
PROVIDED THAT if all Persons entitled to purchase or receive such Securities are
required to also purchase other securities of the Company, the Investors and/or
Designated Other Stockholders exercising their rights pursuant to this paragraph
shall also be required to purchase the same strip of securities (on the same
terms and conditions) that such other Persons are required to purchase. The
purchase price for all Securities offered to the Investors and the Designated
Other Stockholders shall be payable in cash or, to the extent otherwise
consistent with the terms offered to any other Persons, installments over time.

          (b)  In order to exercise its purchase rights hereunder, an Investor
or Designated Other Stockholder, as the case may be, must within 20 days after
receipt of written notice from the Company describing in reasonable detail the
Securities being offered, the purchase price thereof, the payment terms and such
Investor's or Designated Other Stockholder's percentage allotment deliver a
written notice to the Company describing its election hereunder. If all of the
Securities offered to the Investors and the Designated Other Stockholders are
not fully subscribed by such Stockholders, the remaining Securities shall be
reoffered by the Company to the Investors and the Designated Other Stockholders
purchasing their full allotment upon the terms set forth in this paragraph,
except that such holders must exercise their purchase rights within five (5)
days after receipt of such reoffer.

          (c)  Upon the expiration of the offering periods described above, the
Company shall be entitled to sell such Securities which the Investors and the
Designated Other Stockholders have not elected to purchase during the 60 days
following such expiration on terms and conditions no more favorable to the
purchasers thereof than those offered to such holders. Any Securities offered or
sold by the Company after such 60-day period must be reoffered to the Investors
and the Designated Other Stockholders pursuant to the terms of this paragraph.

          (d)  The provisions of this paragraph 7 shall terminate upon the
consummation of a Qualified Public Offering or a Sale of the Company.

          8.   DEFINITIONS

          "BOARD" has the meaning set forth in the recitals hereto.

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          "CLOSING" has the meaning set forth in the recitals hereto.

          "COMMON STOCK" has the meaning set forth in the recitals hereto.

          "COMPANY" has the meaning set forth in the preamble hereto.

          "DESIGNATED OTHER STOCKHOLDER" means each of G-Bar Limited
Partnership, Avrum Gray Delta Trust, David Kalt and Ned Bennett, so long as, in
each such case, such Designated Other Stockholder holds at least fifty percent
(50%) of the Common Stock held by such Designated Other Stockholder on the date
hereof.

          "DESIGNATED OTHER STOCKHOLDER GROUP" means the following Other
Stockholders: G-Bar Limited Partnership ("G-BAR"); Avrum Gray Delta Trust; David
Kalt; Ned Bennett; Delaware Charter F/B/O Ned Bennett; John R. Anderson
Revocable Trust; Gregory DeFalco; Lee Silver; Steven R. Kalt, Trustee; Allan S.
Kalt Revocable Trust; Scott and Emily Kalt; Philip Danley Revocable Trust; Sean
Sulivan Living Trust; Rodrigo Levy; Matt Gray; Harold Kalt Revocable Trust; Jeff
Kalt; Mark A. Kalt Revocable Trust; and Ian and Diane Galleher. For purposes of
the foregoing, (i) G-Bar shall cease to be a member of the Designated Other
Stockholder Group if and when either (a) G-Bar is sold to a third party or (b)
the members of the Gray Family Group cease to directly own or control a majority
of the partnership interests therein (i.e., cease to be allocated a majority of
the partnership gains and losses) or cease to control G-Bar's general partner
and (ii) no Person who receives Stockholder Shares from G-Bar following a
permitted distribution thereof by G-Bar shall be deemed to be a member of the
Designated Other Stockholder Group unless such Person is either listed above or
is a member of the Gray Family Group.

          "EQUITY INCENTIVE PLAN" means the optionsXpress, Inc. 2001 Equity
Incentive Plan and any employee option or stock incentive plan that may be
adopted by the Board from time to time, pursuant to which the Company may grant
Common Stock and/or options to purchase Common Stock to officers, directors,
employees and consultants of the Company.

          "EQUITY VALUE" has the meaning given to such term in that certain
Investor Rights Agreement, dated as of the date hereof, by and among the Company
and the Investors (as the same may be amended or modified from time to time in
accordance with its terms).

          "EXISTING PREFERRED" has the meaning set forth in the Purchase
Agreement (as the same may be amended or modified from time to time in
accordance with its terms)

          "GRAY FAMILY GROUP" means, collectively, each of James Gray and Avrum
Gray and each of their respective spouses, descendants (whether natural or
adopted) and/or ancestors, and any partnership, limited liability company or
trust established principally for the benefit of any of the foregoing
individuals.

          "INVESTOR DIRECTOR" has the meaning set forth in paragraph 1 above.

          "INVESTORS" means those Persons identified on the SCHEDULE OF
INVESTORS attached hereto and such other Persons as may become "Investors"
hereunder from time to time under the circumstances described in paragraph 5
above.

                                      -10-
<Page>

          "INVESTOR RIGHTS AGREEMENT" has the meaning set forth in the preamble
hereto.

          "OPTION ADJUSTMENT DIVIDEND" has the meaning set forth in the
Company's Certificate of Incorporation.

          "OTHER STOCKHOLDERS" means those Persons identified on the SCHEDULE OF
OTHER STOCKHOLDERS attached hereto and such other Persons as may become "Other
Stockholders" hereunder from time to time under the circumstances described in
paragraph 5 above.

          "OTHER STOCKHOLDER DIRECTORS" has the meaning set forth in paragraph 1
above.

          "OUTSIDE DIRECTOR" has the meaning set forth in paragraph 1 above.

          "PERSON" means an individual, a partnership, a corporation, a limited
liability company, an association, a joint stock company, a trust, a joint
venture, an unincorporated organization and a governmental entity or any
department, agency or political subdivision thereof.

          "PUBLIC SALE" means any sale of Stockholder Shares to the public
pursuant to an offering registered under the Securities Act or to the public
through a broker, dealer or market maker pursuant to the provisions of Rule 144
adopted under the Securities Act (or any similar provision then in force).

          "PUBLIC OFFERING" means any offering by the Company of its Common
Stock to the public pursuant to an effective registration statement under the
Securities Act or any comparable statement under any similar federal statute
then in force.

          "PURCHASE AGREEMENT" has the meaning set forth in the recitals hereto.

          "QUALIFIED PUBLIC OFFERING" has the meaning set forth in the Company's
Certificate of Incorporation.

          "QUALIFIED SALE" has the meaning set forth in the Company's
Certificate of Incorporation.

          "REGISTRATION AGREEMENT" has the meaning set forth in the Purchase
Agreement (as the same may be amended or modified from time to time in
accordance with its terms).

          "SALE OF THE COMPANY" means a sale of the Company pursuant to which
one or more Persons acquire (i) all or substantially all of the capital stock of
the Company (whether by merger, consolidation, sale or transfer of the Company's
capital stock or otherwise) or (ii) all or substantially all of the Company's
assets determined on a consolidated basis.

          "SECURITIES" has the meaning set forth in paragraph 7.

          "SECURITIES ACT" means the Securities Act of 1933, as amended from
time to time.

          "SERIES A PREFERRED" has the meaning set forth in the recitals hereto.

                                      -11-
<Page>

          "STOCKHOLDER" has the meaning set forth in the preamble hereto.

          "STOCKHOLDER SHARES" means (i) any Common Stock purchased or otherwise
acquired or held by any Stockholder, (ii) any Common Stock issued or issuable
directly or indirectly upon the conversion, exercise or exchange of any
securities purchased or otherwise acquired by any Stockholder which are
convertible into or exercisable or exchangeable directly or indirectly for
Common Stock (including the Series A Preferred and the Existing Preferred but
excluding options to purchase Common Stock granted by the Company unless and
until such options are exercised) and (iii) any other capital stock or equity
securities issued or issuable directly or indirectly with respect to the
securities referred to in clauses (i) or (ii) above by way of a stock dividend
or stock split or in connection with a combination of shares, recapitalization,
merger, consolidation or other reorganization. As to any particular securities
constituting Stockholder Shares hereunder, such Stockholder Shares shall cease
to be Stockholder Shares hereunder when they have been (x) effectively
registered under the Securities Act and disposed of in accordance with the
registration statement covering them or (y) sold to the public through a broker,
dealer or market maker pursuant to Rule 144 (or any similar provision then in
force) under the Securities Act.

          "SUBSIDIARY" means, with respect to any Person, any corporation,
limited liability company, partnership, association or other business entity of
which (i) if a corporation, a majority of the total voting power of shares of
stock entitled (without regard to the occurrence of any contingency) to vote in
the election of directors or trustees thereof is at the time owned or
controlled, directly or indirectly, by that Person or one or more Subsidiaries
of that Person or a combination thereof, or (ii) if a limited liability company,
partnership, association or other business entity, a majority of the limited
liability company, partnership or other similar ownership interest thereof is at
the time owned or controlled, directly or indirectly, by that Person or one or
more Subsidiaries of that Person or a combination thereof. For purposes hereof,
a Person or Persons shall be deemed to have a majority ownership interest in a
limited liability company, partnership, association or other business entity if
such Person or Persons shall be allocated a majority of the limited liability
company, partnership, association or other business entity gains or losses or
shall be or control the managing member, general partner or managing director of
such limited liability company, partnership, association or other business
entity.

          9.   TRANSFERS IN VIOLATION OF AGREEMENT. Any Transfer or attempted
Transfer of any Stockholder Shares in violation of any provision of this
Agreement shall be void, and the Company shall not record such Transfer on its
books or treat any purported transferee of such Stockholder Shares as the owner
of such Stockholder Shares for any purpose.

          10.  AMENDMENTS AND WAIVERS. Except as otherwise provided herein, no
modification, amendment or waiver of any provision of this Agreement shall be
effective against the Company or the Stockholders unless such modification,
amendment or waiver is approved in writing by the Company, the Investors that
held a majority of the Stockholder Shares then held by the Investors and the
Other Stockholders that held a majority of the Stockholder Shares then held by
the Other Stockholders. The failure of any party to enforce any of the
provisions of this Agreement shall in no way be construed as a waiver of such
provisions and shall not affect the

                                      -12-
<Page>

right of such party thereafter to enforce each and every provision of this
Agreement in accordance with its terms.

          11.  SEVERABILITY. Whenever possible, each provision of this Agreement
shall be interpreted in such manner as to be effective and valid under
applicable law, but if any provision of this Agreement is held to be invalid,
illegal or unenforceable in any respect under any applicable law or rule in any
jurisdiction, such invalidity, illegality or unenforceability shall not affect
the validity, legality or enforceability of any other provision of this
Agreement in such jurisdiction or affect the validity, legality or
enforceability of any provision in any other jurisdiction, but this Agreement
shall be reformed, construed and enforced in such jurisdiction as if such
invalid, illegal or unenforceable provision had never been contained herein.

          12.  ENTIRE AGREEMENT. Except for the Investor Rights Agreement and
the Restricted Stock Agreements and as otherwise expressly set forth herein,
this Agreement embodies the complete agreement and understanding among the
parties hereto with respect to the subject matter hereof and supersedes and
preempts any prior understandings, agreements or representations by or among the
parties, written or oral, which may have related to the subject matter hereof in
any way.

          13.  SUCCESSORS AND ASSIGNS. Except as otherwise expressly provided
herein, this Agreement shall bind and inure to the benefit of and be enforceable
by the Company and its successors and assigns and the Stockholders and any
subsequent holders of Stockholder Shares and the respective successors and
assigns of each of them, so long as they hold Stockholder Shares (except that
the rights of the Other Stockholders under paragraph 3(b) above shall not be
assignable by the Other Stockholders (whether in connection with the transfer of
Stockholder Shares or otherwise)).

          14.  COUNTERPARTS. This Agreement may be executed in multiple
counterparts (including by means of telecopied signature pages), each of which
shall be an original and all of which taken together shall constitute one and
the same agreement.

          15.  REMEDIES. The parties hereto shall be entitled to enforce their
rights under this Agreement specifically, to recover damages by reason of any
breach of any provision of this Agreement and to exercise all other rights
existing in their favor. The parties hereto agree and acknowledge that money
damages would not be an adequate remedy for any breach of the provisions of this
Agreement and that the Company and any Stockholder may in its sole discretion
apply to any court of law or equity of competent jurisdiction for specific
performance and/or injunctive relief (without posting a bond or other security)
in order to enforce or prevent any violation of the provisions of this
Agreement.

          16.  EXCESS CONSIDERATION. If and to the extent that any Other
Stockholder receives any consideration in connection with a Qualified Sale in
excess of arm's length compensation (as determined by the Compensation Committee
of the Board pursuant to clause (3) of subparagraph (v) of paragraph 1C of that
certain Investor Rights Agreement, dated as of the date hereof, by and among the
Company and the Investors (as the same may be amended or modified from time to
time in accordance with its terms)), such Other Stockholder agrees to allocate
such excess consideration to each of the Investors and the Company's other
stockholders

                                      -13-
<Page>

pro rata based upon the aggregate consideration otherwise payable to the
Investors and the Company's other stockholders in connection with such Qualified
Sale.

          17.  NOTICES. Any notice provided for in this Agreement shall be in
writing and shall be either personally delivered, mailed first class mail
(postage prepaid), sent by reputable overnight courier service (charges prepaid)
or sent by facsimile to the Company at the address set forth below and to any
other recipient at the address indicated on the Schedules hereto and to any
subsequent Stockholder subject to this Agreement at such address as indicated by
the Company's records, or at such address or to the attention of such other
Person as the recipient party has specified by prior written notice to the
sending party. Notices shall be deemed to have been given hereunder when
delivered personally, five (5) days after deposit in the U.S. mail, one day
after deposit with a reputable overnight courier service (charges prepaid) or
upon machine-generated acknowledgment of receipt after being transmitted by
facsimile. The Company's address is:

               optionsXpress, Inc.
               39 South LaSalle Street
               Suite 220
               Chicago, Illinois 60603
               Attention:  President
               Telephone:  (888) 280-8020
               Telecopy:   (312) 629-5256

               WITH A COPY TO:
               (which shall not constitute notice to the Company)

               KMZ Rosenman
               525 West Monroe Street
               Suite 1600
               Chicago, Illinois 60661-7693
               Attention:  Mathew Brown, Esq.
               Telephone:  (312) 902-5200
               Telecopy:   (312) 902-1061

          18.  GOVERNING LAW. The corporate law of the State of Delaware shall
govern all issues concerning the relative rights of the Company and its
Stockholders. All other issues and questions concerning the construction,
validity, enforcement and interpretation of this Agreement and the schedules
hereto shall be governed by, and construed in accordance with, the laws of the
State of Delaware without giving effect to any choice of law or conflict of law
rules or provisions (whether of the State of Delaware or any other jurisdiction)
that would cause the application of the laws of any jurisdiction other than the
State of Delaware.

          19.  WAIVER OF PREEMPTIVE RIGHTS. Each of the Other Stockholders
hereby waives any existing preemptive rights with respect to the issuance and
sale of the Series A Preferred under the Purchase Agreement and the issuance of
any Common Stock upon conversion thereof. In addition, each Other Stockholder
that is a party to the Investor Rights Agreement hereby waives any and all
preemptive rights that such Other Stockholder has or may

                                      -14-
<Page>

have with respect to issuances of securities by the Company following the date
hereof pursuant to the Investor Rights Agreement, and hereby acknowledges that
the provisions of Section 2 of the Investor Rights Agreement are null and void
and of no further force or effect with respect to such Other Stockholder. Each
Designated Other Stockholder hereby agrees that the provisions of paragraph 7
hereof supersede and replace in their entirety the provisions of Section 2 of
the Investor Rights Agreement.

          20.  BUSINESS DAYS. If any time period for giving notice or taking
action hereunder expires on a day which is a Saturday, Sunday or legal holiday
in the state in which the Company's chief executive office is then located, the
time period shall automatically be extended to the business day immediately
following such Saturday, Sunday or legal holiday.

          21.  DESCRIPTIVE HEADINGS, ETC. The descriptive headings of this
Agreement are inserted for convenience only and do not constitute a part of this
Agreement. The use of the term "including" herein shall mean "including without
limitation."

          22.  NO STRICT CONSTRUCTION. The parties hereto have participated
jointly in the negotiation and drafting of this Agreement. In the event an
ambiguity or question or intent or interpretation arises, this Agreement shall
be construed as it was drafted jointly by the parties hereto, and no presumption
or burden of proof shall arise favoring or disfavoring any party hereto by
virtue of the authorship of any of the provisions of this Agreement. The parties
hereto intend that each covenant contained herein shall have independent
significance. If any party has breached any covenant contained herein in any
respect, the fact that there exists another covenant relating to the same or
similar subject matter (regardless of the relative levels of speciality) which
the party has not breached shall not detract from or mitigate the fact that the
party is in breach of the first covenant.

                                    * * * * *

                                      -15-
<Page>

          IN WITNESS WHEREOF, the parties hereto have executed this Stockholders
Agreement on the day and year first above written.

                                         OPTIONSXPRESS, INC.

                                         By:  /s/ DAVID KALT
                                              ----------------------------------
                                         Its: President
                                              ----------------------------------

                                         G-BAR LIMITED PARTNERSHIP

                                         By:  /s/ JAMES GRAY
                                              ----------------------------------
                                         Its: General Partner

                                         AVRUM GRAY DELTA TRUST FOR JIM
                                         U/A/D JUNE 7, 2002

                                         By:  /s/ JAMES GRAY
                                              ----------------------------------
                                         Its: Trustee

                                              /s/ DAVID KALT
                                              ----------------------------------
                                              David Kalt

                                              /s/ NED BENNETT
                                              ----------------------------------
                                              Ned Bennett

                                         DELAWARE CHARTER GUARANTEE &
                                         TRUST COMPANY F/B/O NED BENNETT
                                         IRA

                                         By:  /s/ NED BENNETT
                                              ----------------------------------
                                         Its: Trustee

<Page>

                                         SUMMIT VENTURES VI-A, L.P.

                                         By:  Summit Partners VI (GP), L.P.
                                         Its: General Partner

                                         By:  Summit Partners VI (GP), LLC
                                         Its: General Partner

                                         By:  /s/ BRUCE EVANS
                                              ----------------------------------
                                         Its: Member

                                         SUMMIT VENTURES VI-B, L.P.

                                         By:  Summit Partners VI (GP), L.P.
                                         Its: General Partner

                                         By:  Summit Partners VI (GP), LLC
                                         Its: General Partner

                                         By:  /s/ BRUCE EVANS
                                              ----------------------------------
                                         Its: Member

                                         SUMMIT VI ADVISORS FUND, L.P.

                                         By:  Summit Partners VI (GP), L.P.
                                         Its: General Partner

                                         By:  Summit Partners VI (GP), LLC
                                         Its: General Partner

                                         By:  /s/ BRUCE EVANS
                                              ----------------------------------
                                         Its: Member

<Page>

                                         SUMMIT VI ENTREPRENEURS FUND, L.P.

                                         By:  Summit Partners VI (GP), L.P.
                                         Its: General Partner

                                         By:  Summit Partners VI (GP), LLC
                                         Its: General Partner

                                         By:  /s/ BRUCE EVANS
                                              ----------------------------------
                                         Its: Member

                                         SUMMIT INVESTORS VI, L.P.

                                         By:  Summit Partners VI (GP), L.P.
                                         Its: General Partner

                                         By:  Summit Partners VI (GP), LLC
                                         Its: General Partner

                                         By:  /s/ BRUCE EVANS
                                              ----------------------------------
                                         Its: Member

<Page>

                              SCHEDULE OF INVESTORS

Summit Ventures VI-A, L.P.
Summit Ventures VI-B, L.P.
Summit VI Advisors Fund, L.P.
Summit VI Entrepreneurs Fund, L.P.
Summit Investors VI, L.P.

c/o Summit Partners, L.P.
222 Berkeley Street
18th Floor
Boston, Massachusetts 02116
Telephone:    (617) 824-1000
Telecopy:     (617) 824-1100
Attention:    Mr. Bruce R. Evans

WITH A COPY TO:
(which shall not constitute notice to the Investors)

Kirkland & Ellis LLP
200 East Randolph Drive
Chicago, Illinois 60601
Attn:  Ted H. Zook, P.C.

<Page>

                         SCHEDULE OF OTHER STOCKHOLDERS

                               NAMES AND ADDRESSES

G-Bar Limited Partnership
440 S. LaSalle Street, Suite 650
Chicago, IL 60605

Avrum Gray Delta Trust for Jim U/A/D June 7, 2002
440 S. LaSalle Street, Suite 650
Chicago, IL 60605

David Kalt
39 S. LaSalle Street, Suite 220
Chicago, IL 60603

Ned Bennett
200 Granada Street
El Paso, TX 79912

Delaware Charter Guarantee & Trust Company F/B/O Ned Bennett IRA
200 Granada Street
El Paso, TX 79912

[Other Post-Signing Other Stockholders]<Page>

                                                                    Exhibit 10.3

                               OPTIONSXPRESS, INC.
                            INVESTOR RIGHTS AGREEMENT

          THIS AGREEMENT is made as of January 15, 2004 by and among
optionsXpress, Inc., a Delaware corporation (the "COMPANY"), and the Persons
listed on the SCHEDULE OF INVESTORS attached hereto (each, an "INVESTOR" and
collectively, the "INVESTORS").

          WHEREAS, the parties to this Agreement are parties to a Stock Purchase
and Recapitalization Agreement, dated as of December 17, 2003 (the
"RECAPITALIZATION AGREEMENT"), pursuant to which the Investors shall purchase
shares of the Company's Series A Convertible Preferred Stock, par value $.0001
per share (the "SERIES A PREFERRED");

          WHEREAS, in order to induce the Investors to enter into the
Recapitalization Agreement and consummate the transactions contemplated thereby,
the Company has agreed to enter into this Agreement for the benefit of the
Investors;

          WHEREAS, the execution and delivery of this Agreement is a condition
to the Closing under the Recapitalization Agreement; and

          WHEREAS, unless otherwise provided in this Agreement, capitalized
terms used herein shall have the meanings set forth in Section 2 hereof.

          NOW, THEREFORE, in consideration of the mutual covenants contained
herein and other good and valuable consideration, the receipt and sufficiency of
which are hereby acknowledged, the parties to this Agreement hereby agree as
follows:

          Section 1.   COVENANTS.

          1A.  FINANCIAL STATEMENTS AND OTHER INFORMATION. The Company shall
deliver to (or, in the case of subparagraph (vi) below, shall make available for
inspection by) the Designated Investor (so long as the Investors who are
original signatories hereto and/or their affiliated investment funds
collectively hold at least 10% of the Series A Preferred or at least 10% of the
Underlying Common Stock originally issued to the Investors as of the date
hereof) and to each holder of at least 10% of the outstanding Series A Preferred
and each holder of at least 10% of the Underlying Common Stock:

               (i)      as soon as available but in any event within 30 days
     after the end of each monthly accounting period in each fiscal year,
     unaudited consolidating and consolidated statements of income and cash
     flows of the Company and its Subsidiaries for such monthly period and for
     the period from the beginning of the fiscal year to the end of such month,
     and unaudited consolidating and consolidated balance sheets of the Company
     and its Subsidiaries as of the end of such monthly period, setting forth
     for each monthly period in each fiscal year comparisons to the Company's
     budget and to the corresponding period in the preceding fiscal year, and
     all such statements setting forth the results of a fiscal quarter of the
     Company shall be prepared in accordance with GAAP,

<Page>

consistently applied as applicable to interim period financial statements
(except for the absence of footnote disclosures with respect thereto and subject
to changes resulting from normal year-end adjustments for recurring accruals,
and, except that in the case of monthly unaudited financial statements, such
statements shall consist of the regular reports prepared for management, which
may or may not be in accordance with GAAP);

               (ii)     within 90 days after the end of each fiscal year,
     consolidating and consolidated statements of income and cash flows of the
     Company and its Subsidiaries for such fiscal year, and consolidating and
     consolidated balance sheets of the Company and its Subsidiaries as of the
     end of such fiscal year, all prepared in accordance with GAAP, consistently
     applied, and accompanied by (a) with respect to the consolidated portions
     of such statements, an opinion of a "Big Four" accounting firm selected by
     the Company's board of directors containing no exceptions or qualifications
     regarding compliance with GAAP or otherwise, (b) a copy of such firm's
     annual management letter to the Company's board of directors, if any, and
     (c) in each case, comparisons to the Company's annual budget and to the
     preceding fiscal year;

               (iii)    promptly upon receipt thereof, any additional reports,
     management letters or other detailed information concerning significant
     aspects of the Company's operations or financial affairs given to the
     Company by its independent accountants (and not otherwise contained in
     other materials provided hereunder);

               (iv)     at least 30 days but no more than 60 days prior to the
     beginning of each fiscal year, an annual budget and operating plan prepared
     on a monthly basis for the Company and its Subsidiaries for such fiscal
     year (displaying anticipated statements of income and cash flows and
     balance sheets), and promptly upon preparation thereof any other
     significant budgets or operating plans prepared by the Company and any
     revisions of such annual or other budgets or operating plans (the annual
     budget ("projections") and operating plan for 2004 having been delivered
     prior to the date hereof);

               (v)      promptly (but in any event within five business days)
     after the discovery or receipt of notice of any Event of Noncompliance, any
     default under any material agreement to which the Company or any of its
     Subsidiaries is a party which could reasonably be anticipated to have a
     material adverse effect upon the business, financial condition, operating
     results, value, assets, operations or business prospects of the Company and
     its Subsidiaries taken as a whole, or any other material adverse change,
     event or circumstance affecting the Company and its Subsidiaries taken as a
     whole (including, without limitation, the filing of any material litigation
     against the Company or any Subsidiary or the existence of any dispute with
     any Person which the Company believes is reasonably likely to lead to such
     litigation being commenced), a notice letter from the Company specifying
     the same; and

               (vi)     with reasonable promptness, make available for
     inspection such other information and financial data concerning the Company
     and its Subsidiaries as the holders of a majority of the outstanding Series
     A Preferred may reasonably request.

                                     - 2 -
<Page>

Each of the financial statements referred to in subparagraphs (i) and (ii) above
shall be true and correct in all material respects as of the dates and for the
periods set forth therein, subject in the case of the unaudited financial
statements to the absence of footnote disclosures with respect thereto and
changes resulting from normal year-end adjustments for recurring accruals, and
except that, in the case of the monthly unaudited financial statements, such
statements shall consist of the regular reports prepared for management, which
may or may not be in accordance with GAAP. Notwithstanding the foregoing, the
provisions of this paragraph 1A and paragraph 1B below shall cease to be
effective so long as the Company is subject to the periodic reporting
requirements of the Securities Exchange Act and continues to comply with such
requirements. Except as otherwise required by law or judicial order or decree or
by any governmental agency or authority, each Person entitled to receive
information regarding the Company and its Subsidiaries under this paragraph 1A
or paragraph 1B below shall use the same standards and controls which such
Person uses to maintain the confidentiality of its own confidential information
(but in no event less than reasonable care) to maintain the confidentiality of
all nonpublic information of the Company or any of its Subsidiaries obtained by
it pursuant to this paragraph 1A or paragraph 1B below; PROVIDED THAT,
notwithstanding the foregoing or the provisions of any confidentiality agreement
in favor of the Company, each such Person may disclose such information in
connection with the sale or transfer of any Series A Preferred or Underlying
Common Stock if such Person's transferee agrees in writing to be bound by the
provisions hereof. For purposes of this Agreement and the Registration
Agreement, all holdings of Series A Preferred and Underlying Common Stock by
Persons who are Affiliates of each other shall be aggregated for purposes of
meeting any threshold tests under this Agreement and the Registration Agreement.

          1B.  INSPECTION OF PROPERTY. The Company shall permit any
representatives designated by any Investor (so long as the Investors who are the
original signatories hereto and/or their affiliated investment funds
collectively hold at least 25% of the Series A Preferred and/or at least 25% of
the Underlying Common Stock originally issued to the Investors as of the date
hereof) or any holder of at least 25% of the outstanding Series A Preferred or
at least 25% of the Underlying Common Stock, upon reasonable notice and during
normal business hours and at such other times as any such holder may reasonably
request, to (i) visit and inspect any of the properties of the Company and its
Subsidiaries, (ii) examine the corporate and financial records of the Company
and its Subsidiaries and make copies thereof and (iii) consult with the
directors, officers, key employees and independent accountants of the Company
and its Subsidiaries concerning the affairs, finances and accounts of the
Company and its Subsidiaries. The presentation of an executed copy of this
Agreement by any Investor or any such holder of Series A Preferred or Underlying
Common Stock, along with reasonable evidence of compliance with the Series A
Preferred or Underlying Common Stock ownership thresholds set forth immediately
above, to the Company's independent accountants shall constitute the Company's
permission to its independent accountants to participate in discussions with
such Persons.

          1C.  CERTAIN NEGATIVE COVENANTS. So long as the Investors who are
the original signatories hereto and/or their affiliated investment funds
collectively hold at least 25% of the Series A Preferred originally issued as of
the date hereof, the Company shall not (without the prior written consent of the
holders of a majority of the outstanding Series A Preferred):

                                     - 3 -
<Page>

               (i)      directly or indirectly declare or pay, or permit any
     Subsidiary to declare or pay, any dividends or make any distributions upon
     any of its capital stock or other equity securities, except that (a) the
     Company may declare and pay dividends payable in shares of its Common Stock
     issued upon the outstanding shares of its Common Stock (including but not
     limited to an Option Adjustment Dividend) and any Subsidiary may declare
     and pay dividends or make distributions to the Company or any Wholly-Owned
     Subsidiary, (b) the Company may declare and pay cash dividends upon its
     outstanding Common Stock and the Series A Preferred (on an as-if-converted
     basis) pursuant to Section 1 of Part D of Article IV of the Company's
     Certificate of Incorporation so long as (1) the Company's Tangible Net
     Worth (as determined immediately after giving effect to the declaration and
     payment of any such dividends) is not less than $20,000,000, (2) the
     aggregate dividends declared and paid in any calendar year do not exceed
     80% of the Company's after-tax net income for such calendar year (as
     determined on a consolidated basis in accordance with GAAP) AND (3) the
     Company's Equity Value (as determined immediately after giving effect to
     the declaration and payment of such dividends) is not less than
     $180,000,000, (c) the Company may declare and pay the Net Book Value
     Dividend (as defined in the Recapitalization Agreement) pursuant to the
     terms of Paragraph 1F of the Recapitalization Agreement, and (d) the
     Company may declare and pay Stock Option Proceeds Dividends (as defined in
     the Company's Certificate of Incorporation);

               (ii)     directly or indirectly redeem, purchase or otherwise
     acquire, or permit any Subsidiary to redeem, purchase or otherwise acquire,
     any of the Company's or any Subsidiary's capital stock or other equity
     securities (including, without limitation, warrants, options and other
     rights to acquire such capital stock or other equity securities), other
     than (a) the Series A Preferred pursuant to the terms of the Certificate of
     Incorporation, (b) repurchases of Common Stock from former employees of the
     Company and its Subsidiaries upon termination of employment for an
     aggregate purchase price of no more than $250,000 in any twelve-month
     period pursuant to arrangements approved by the Company's board of
     directors; or directly or indirectly redeem, purchase or make any payments
     with respect to any stock appreciation rights, phantom stock plans or
     similar rights or plans or (c) pursuant to a Put Request (as defined in the
     Restricted Stock Agreements);

               (iii)    authorize, issue or enter into any agreement providing
     for the issuance (contingent or otherwise) of (a) any notes or debt
     securities containing equity features (including, without limitation, any
     notes or debt securities convertible into or exchangeable for capital stock
     or other equity securities, issued in connection with the issuance of
     capital stock or other equity securities or containing profit participation
     features), (b) any capital stock or other equity securities (or any
     securities convertible into or exchangeable for any capital stock or other
     equity securities) which are senior to or on a parity with the Series A
     Preferred with respect to the payment of dividends, redemptions,
     distributions upon liquidation or otherwise, or (c) any additional shares
     of Series A Preferred;

               (iv)     make, or permit any Subsidiary to make, any loans or
     advances to, guarantees for the benefit of, or Investments in, any Person
     (other than a Wholly-Owned

                                     - 4 -
<Page>

     Subsidiary established under the laws of a jurisdiction of the United
     States or any of its territorial possessions and, subject to compliance
     with subparagraph (xiv) below, any other Wholly-Owned Subsidiary), except
     for (a) reasonable advances to employees in the ordinary course of business
     (but expressly prohibiting any loans or the arranging of any loans to or
     for the benefit of any employees for any purpose), (b) acquisitions as
     described in and as otherwise permitted pursuant to subparagraph (viii)
     below, (c) Investments otherwise permitted pursuant to clause (xvii) below
     that do not involve the purchase or acquisition of a majority or
     controlling interest in any company or business and (d) Investments having
     a stated maturity no greater than one year from the date the Company or any
     Subsidiary makes such Investment in (1) obligations of the United States
     government or any agency thereof or obligations guaranteed by the United
     States government, (2) certificates of deposit of commercial banks having
     combined capital and surplus of at least $50 million or (3) commercial
     paper with a rating of at least "Prime-1" by Moody's Investors Service,
     Inc.;

               (v)      merge or consolidate with any Person or, except as
     permitted by subparagraph (viii) below, permit any Subsidiary to merge or
     consolidate with any Person (other than (a) a merger of a Wholly-Owned
     Subsidiary with another Wholly-Owned Subsidiary or (b) a transaction
     structured as a merger with an Independent Third Party (whether or not the
     Company is the surviving corporation) on reasonable market terms in which
     (1) the consideration to be received or thereafter held by the Company's
     stockholders as a result thereof in respect of all of the Company's
     outstanding capital stock held by such stockholders immediately prior to
     such merger transaction consists solely of cash and/or freely and
     immediately tradeable public company securities resulting from a
     combination with a company with an aggregate "public float" of not less
     than $400,000,000 and an aggregate market equity capitalization of not less
     than $1,000,000,000, in each case as determined immediately prior to such
     merger transaction, (2) all holders of Common Stock (including the holders
     of Series A Preferred on an as-if-converted-basis) receive the same form
     and amount of consideration per share of Common Stock, or, if any holders
     of Common Stock are given an option as to the form and consideration to be
     received, all holders are given the same option, (3) the Investors and the
     Company's other stockholders receive their pro rata share of all
     consideration (however described or allocated) that is paid to any of the
     Company's other stockholders in connection with such transaction that is
     not for the sale of capital stock (including, without limitation, for
     purposes hereof any compensation or other amounts payable in respect of any
     management, consulting or similar agreements, noncompete or other
     restrictive covenants or change-in-control or retention or other payments
     however described which is in excess of arm's length compensation for the
     consideration or services to be provided therefor as determined by the
     members of the compensation committee of the Company's board of directors
     (but with any member of the compensation committee abstaining from
     participation in any such determination with regard to any such
     consideration to be received by such member)) and (4) the Investors who are
     original signatories hereto receive at the closing of such transaction
     aggregate consideration in respect of the Series A Preferred and Underlying
     Common Stock held by them immediately prior to such closing equal to not
     less than two (2) times the allocable portion of the original investment
     amount with respect to such shares) (with any

                                     - 5 -
<Page>

     transaction described in clause (b) immediately above being referred to
     herein as a "QUALIFIED SALE"));

               (vi)     sell, lease or (other than pursuant to a Qualified Sale)
     otherwise dispose of, or permit any Subsidiary to sell, lease or (other
     than pursuant to a Qualified Sale) otherwise dispose of, more than 15% of
     the consolidated assets (including, without limitation, the capital stock
     of any Subsidiaries) of the Company and its Subsidiaries (computed on the
     basis of book value, determined in accordance with GAAP consistently
     applied, contribution to the Company's revenues or earnings, or fair market
     value, determined by the Company's board of directors in its reasonable
     good faith judgment) in any transaction or series of related transactions;
     or, except in the ordinary course of business to an Independent Third Party
     with the prior approval of the Company's board of directors, sell or
     permanently dispose of any of its or any Subsidiary's material Intellectual
     Property Rights;

               (vii)    liquidate, dissolve or effect a recapitalization or
     reorganization in any form of transaction (including, without limitation,
     any reorganization into a limited liability company, a partnership or any
     other non-corporate entity which is treated as a partnership for federal
     income tax purposes, or the formation of a parent holding company for the
     Company);

               (viii)   acquire, or permit any Subsidiary to acquire, any
     majority or controlling interest in any company or business (whether by a
     purchase of assets, purchase of stock, merger or otherwise), or enter into
     any joint venture, if the aggregate consideration related to such
     transaction and any other transactions consummated during the prior
     twelve-month period (including, without limitation, the assumption of
     Indebtedness whether direct or indirect) exceeds 10% of the Company's
     Equity Value determined as of the date of the most recent of such
     transactions;

               (ix)     enter into, or permit any Subsidiary to enter into, the
     ownership, active management or operation of any business that is not
     related to the financial services industry;

               (x)      become subject to, or permit any of its Subsidiaries to
     become subject to, (including, without limitation, by way of amendment to
     or modification, extension or renewal of) any agreement or instrument which
     by its terms would (under any circumstances) restrict (a) the right of any
     Subsidiary to make loans or advances or pay dividends or distributions to,
     transfer property to, or repay any Indebtedness owed to, the Company or
     another Subsidiary or (b) the Company's right to perform the provisions of
     this Agreement, the Registration Agreement, the Stockholders Agreement, the
     Certificate of Incorporation or the Company's Bylaws (including, without
     limitation, provisions relating to the declaration and payment of dividends
     on and the making of redemptions of the Series A Preferred Stock and
     conversions of the Series A Preferred);

               (xi)     make any amendment to the Certificate of Incorporation
     or the Company's Bylaws, or file any resolution of the Company's board of
     directors with the Delaware Secretary of State containing any provisions
     which would increase the number

                                     - 6 -
<Page>

     of authorized shares of Series A Preferred, amend or otherwise change the
     terms of the Series A Preferred or adversely affect or otherwise impair the
     rights or the relative preferences and priorities of the holders of the
     Series A Preferred or the Underlying Common Stock under this Agreement, the
     Certificate of Incorporation, the Company's Bylaws or the Registration
     Agreement or the Stockholders Agreement;

               (xii)    enter into, amend, modify or supplement, or permit any
     Subsidiary to enter into, amend, modify or supplement, any agreement,
     transaction, commitment or arrangement with any of its or any Subsidiary's
     officers, directors, stockholders who hold greater than 3% of the Company's
     outstanding Common Stock, or, with any individual or entity known by any of
     the Company's chairman, president or chief executive officer to be an
     Affiliate of any of the foregoing, or to be related by blood, marriage or
     adoption to any such individual, or with any entity in which (to the
     knowledge of the Company's chairman, president or chief executive officer)
     any such Person or individual owns a beneficial interest, except (without
     duplication) for (a) customary employment arrangements (but not employment
     agreements) and benefit programs on reasonable terms as approved by the
     compensation committee established by the Company's board of directors
     pursuant to the Stockholders Agreement, (b) ordinary course transactions on
     arm's length terms (as determined by the Company's board of directors)
     which do not involve annual payments in excess of $250,000, or (c) as
     otherwise expressly contemplated by this Agreement;

               (xiii)   increase, or permit any Subsidiary to increase, any
     compensation (including salary, bonuses, benefits and other forms of
     current and deferred compensation) payable to any executive officer or
     director of the Company or any Subsidiary, except for increases approved by
     the compensation committee established by the Company's board of directors
     pursuant to the Stockholders Agreement;

               (xiv)    except as permitted by subparagraph (viii) above,
     establish or acquire or permit (a) any Subsidiaries other than Wholly-Owned
     Subsidiaries or (b) any Subsidiaries organized outside of the United States
     and its territorial possessions (other than, in the case of this clause
     (b), in the ordinary course of business so long as the existence of such
     foreign Subsidiaries would not reasonably be expected to restrict the
     Company's ability to perform the provisions of this Agreement, the
     Stockholders Agreement or the Certificate of Incorporation (including,
     without limitation, provisions relating to the declaration and payment of
     dividends on and the making of redemptions of the Series A Preferred
     Stock));

               (xv)     create, incur, assume or suffer to exist, or permit any
     Subsidiary to create, incur, assume or suffer to exist, any Indebtedness
     if, immediately after giving effect thereto, the Company's total
     Indebtedness exceeds three (3) times the Company's Net Worth; or create,
     incur, assume or suffer to exist, or permit any Subsidiary to create,
     incur, assume or suffer to exist, any Liens other than Permitted Liens;

               (xvi)    make, or permit any Subsidiary to make, any capital
     expenditures (including, for purposes of this subparagraph (xvi) and
     without limitation, payments with respect to capitalized leases, as
     determined in accordance with GAAP consistently

                                     - 7 -
<Page>

     applied), exceeding on a consolidated basis during any twelve-month period
     the greater of (a) $2,000,000 in the aggregate or (b) 10% of the Company's
     EBTDA for the trailing twelve (12) months ended immediately prior to the
     date of such determination;

               (xvii)   make, or permit any Subsidiary to make, any Investments
     that do not involve the purchase or acquisition of a majority or
     controlling interest in any company or business exceeding on an aggregate
     basis during any twelve-month period the greater of (a) $2,000,000 in the
     aggregate or (b) 10% of the Company's EBTDA for the trailing twelve (12)
     months ended immediately prior to the date of such determination;

               (xviii)  increase the authorized size of its board of directors
     above five (5) members;

               (xix)    amend or modify the Company's Stock Option Plan as in
     existence as of the date hereof, adopt any new stock option plan or
     employee stock ownership plan or issue any shares of Common Stock or
     options or other rights to acquire shares of Common Stock to its or its
     Subsidiaries' employees, directors, independent contractors or consultants
     other than pursuant to the Company's Stock Option Plan or in an aggregate
     amount greater than 398,216 shares (as such number of shares is equitably
     adjusted for any stock splits, stock dividends and stock combinations
     subsequent to the date hereof and as such number includes all outstanding
     stock options outstanding as of the date of the Recapitalization
     Agreement), issue any shares of Common Stock or options or other rights to
     acquire shares of Common Stock pursuant to the Company's Stock Option Plan
     to any Persons other than the Company's or its Subsidiaries' employees,
     directors, independent contractors or consultants, or grant any options
     having an exercise price less than the fair market value of the Common
     Stock at the time of such grant or that provide for vesting on a basis more
     favorable than four-years (straight line) or that provide for accelerated
     vesting upon an initial public offering;

               (xx)     issue, sell or otherwise transfer (by dividend or
     distribution or otherwise), or permit any Subsidiary to issue, sell or
     otherwise transfer (by dividend or distribution or otherwise), any shares
     of the capital stock, or rights to acquire shares of the capital stock, of
     any Subsidiary to any Person other than the Company or a Wholly-Owned
     Subsidiary (other than in connection with foreign qualifying shares or
     similar local law requirements of a foreign jurisdiction);

               (xxi)    consummate an initial public offering that does not
     constitute a Qualified Public Offering; or

               (xxii)   use, or permit any Subsidiary to use, the proceeds from
     the sale of the Series A Preferred other than to repurchase shares of
     Common Stock pursuant to the Recapitalization Agreement and for working
     capital purposes.

          1D.  CERTAIN AFFIRMATIVE COVENANTS. So long as the Investors who are
original signatories hereto and/or their affiliated investment funds
collectively hold at least 25% of the Series A Preferred originally issued as of
the date hereof, the Company shall, and shall cause

                                     - 8 -
<Page>

each Subsidiary to (unless it has received the prior written consent of the
holders of a majority of the outstanding Series A Preferred):

               (i)      at all times cause to be done all things necessary to
     maintain, preserve and renew its corporate existence and all material
     licenses, authorizations and permits necessary to the conduct of its
     businesses;

               (ii)     maintain and keep its material properties in good
     working order and condition, and from time to time make all necessary
     repairs, renewals and replacements, so that its businesses may be properly
     conducted in all material respects at all times;

               (iii)    pay and discharge when payable all material taxes,
     assessments and governmental charges imposed upon its properties or upon
     the income or profits therefrom (in each case before the same becomes
     delinquent and before penalties accrue thereon) and all material claims for
     labor, materials or supplies which if unpaid would by law become a Lien
     upon any of its property, unless and to the extent that the same are being
     contested in good faith and by appropriate proceedings and adequate
     reserves (as determined in accordance with GAAP consistently applied) have
     been established on its books with respect thereto;

               (iv)     comply with all other material obligations which it
     incurs pursuant to any contract or agreement, whether oral or written,
     express or implied, as such obligations become due, to the extent a failure
     to so comply could have a material adverse effect upon the business,
     financial condition, operating results, value, assets, operations or
     business prospects of the Company and its Subsidiaries taken as a whole,
     unless and to the extent that the same are being contested in good faith
     and by appropriate proceedings and adequate reserves (as determined in
     accordance with GAAP consistently applied) have been established on its
     books with respect thereto;

               (v)      comply with all applicable laws, rules and regulations
     of all governmental authorities, the violation of which could reasonably be
     expected to have a material adverse effect upon the financial condition,
     operating results, value, assets, operations or business of the Company and
     its Subsidiaries taken as a whole;

               (vi)     apply for and continue in force with good and
     responsible insurance companies adequate insurance covering risks of such
     types and in such amounts as are customary for corporations of similar size
     engaged in similar lines of business;

               (vii)    use its reasonable efforts to obtain (within 60 days
     following the date hereof) and maintain the key-man life insurance policy
     referred to in paragraph 2M of the Recapitalization Agreement (and not
     borrow against, pledge, assign, modify, cancel or surrender such policy);

               (viii)   maintain all material Intellectual Property Rights
     necessary to the conduct of their respective businesses;

               (ix)     maintain proper books of record and account which
     present fairly in all material respects its financial condition and results
     of operations; and

                                     - 9 -
<Page>

               (x)      use its reasonable best efforts to take all actions
     necessary to make any redemption payments with respect to the Series A
     Preferred which it is required to make pursuant to the Company's
     Certificate of Incorporation, including, without limitation, by
     consummating debt and/or equity financings, recapitalizing and/or, to the
     extent permitted by applicable law, revaluing assets.

          1E.  CURRENT PUBLIC INFORMATION. At all times after the Company has
filed a registration statement with the Securities and Exchange Commission
pursuant to the requirements of either the Securities Act or the Securities
Exchange Act, the Company shall file all reports required to be filed by it
under the Securities Act and the Securities Exchange Act and the rules and
regulations adopted by the Securities and Exchange Commission thereunder and
shall take such further action as any holder or holders of Restricted Securities
may reasonably request, all to the extent required to enable such holders to
sell Restricted Securities pursuant to (i) Rule 144 adopted by the Securities
and Exchange Commission under the Securities Act (as such rule may be amended
from time to time) or any similar rule or regulation hereafter adopted by the
Securities and Exchange Commission or (ii) a registration statement on Form S-2
or S-3 or any similar registration form hereafter adopted by the Securities and
Exchange Commission. Upon request, the Company shall deliver to any holder of
Restricted Securities a written statement as to whether it has complied with
such requirements.

          1F.  AMENDMENT OF OTHER AGREEMENTS. The Company shall not (and shall
not permit its Subsidiaries to) amend, modify or waive any provision of the
Employment Agreements, the Existing Investor Rights Agreement, the Restricted
Stock Agreements or any stock purchase or option agreement or employment or
other agreement entered into between the Company or any of its Subsidiaries and
any of their executive officers or key employees without the prior written
consent of the Company's Board of Directors, including the affirmative vote of
the director elected by the holders of a majority of the Series A Preferred, and
the Company shall (or shall cause its Subsidiaries to) enforce the material
provisions of the Recapitalization Agreement, the Employment Agreements, the
Existing Investor Rights Agreement, the Restricted Stock Agreements and such
stock purchase and option agreements and employment and other agreements and
shall exercise all of its rights and remedies thereunder (including, without
limitation, any repurchase options and first refusal rights) unless it is
otherwise directed by the Company's Board of Directors, including the
affirmative vote of the director elected by the holders of a majority of the
Series A Preferred.

          Section 2.  DEFINITIONS. For the purposes of this Agreement, the
following terms have the meanings set forth below:

          "AFFILIATE" of any particular Person means any other Person
controlling, controlled by or under common control with such particular Person,
where "control" means the possession, directly or indirectly, of the power to
direct the management and policies of a Person whether through the ownership of
voting securities, contract or otherwise, and such control will be presumed if
any Person owns ten percent (10%) or more of the voting capital stock or other
ownership interests, directly or indirectly, of any other Person.

          "CONFIDENTIALITY AND NONCOMPETITION AGREEMENTS" has the meaning given
to that term in the Recapitalization Agreement.

                                     - 10 -
<Page>

          "EXISTING INVESTOR RIGHTS AGREEMENT" means that certain Amended and
Restated Investors' Rights Agreement, dated as of December 19, 2001, by and
among the Company and the Persons set forth on SCHEDULE I attached thereto.

          "DESIGNATED INVESTOR" means Summit Ventures VI-A, L.P.

          "DIRECTOR INDEMNIFICATION AGREEMENT" has the meaning given to such
term in the Recapitalization Agreement.

          "EBTDA" shall mean, for any particular accounting period, the
Company's consolidated net income for such period, PLUS (i) the amount of the
provision for federal, state and local income taxes for such period PLUS (ii)
the amount of depreciation and amortization expense during such period, all as
determined on a consolidated basis in accordance with GAAP.

          "EQUITY VALUE" shall mean, as of any date of determination, the sum of
(A) the Company's EBTDA for the six (6) months ending immediately prior to the
date of such determination as reflected on the Company's consolidated financial
statements for such periods, as delivered to the Investors pursuant to paragraph
1A above, multiplied by twenty (20), PLUS (B) the total amount of unrestricted
cash and unrestricted cash equivalents set forth on the Company's consolidated
balance sheet as of the last month included in such twelve-month period, LESS
(C) the outstanding amount of the Company's total Indebtedness as set forth on
the Company's consolidated balance sheet as of the last month included in such
twelve-month period.

          "GAAP" means United States generally accepted accounting principles.

          "INDEBTEDNESS" means at a particular time, without duplication: (i)
all obligations of such Person for borrowed money or in respect of loans or
advances, (ii) all obligations of such Person evidenced by bonds, debentures,
notes or other similar instruments or debt securities, (iii) all commitments by
which a Person assures a creditor against loss (including contingent
reimbursement obligations with respect to letters of credit and bankers'
acceptances), (iv) all obligations arising from cash/book overdrafts, (v) all
obligations of such Person secured by a Lien on such Person's assets, (vi) all
guarantees of such Person in connection with any of the foregoing and any other
indebtedness guaranteed in any manner by a Person (including guarantees in the
form of an agreement to repurchase or reimburse), (vii) all capital lease
obligations, (viii) all indebtedness for the deferred purchase price of property
with respect to which a Person is liable, contingently or otherwise, as obligor
or otherwise (other than trade payables and other current liabilities incurred
in the ordinary course of business), (ix) all other liabilities classified as
non-current liabilities in accordance with GAAP as of the Closing Date and (x)
all accrued interest, prepayment premiums or penalties related to any of the
foregoing.

          "INDEPENDENT THIRD PARTY" means any Person who, immediately prior to
the contemplated transaction, does not own in excess of 5% of the Company's
Common Stock on a fully-diluted basis (a "5% OWNER"), who is not controlling,
controlled by or under common control with any such 5% Owner and who is not the
spouse or descendent (by birth or adoption) of any such 5% Owner or a trust for
the benefit of such 5% Owner and/or such other Persons.

                                     - 11 -
<Page>

          "INTELLECTUAL PROPERTY RIGHTS" means any and all intellectual and
proprietary rights and rights in confidential information of every kind and
description anywhere in the world, including all (i) patents, patent
applications, patent disclosures and inventions, (ii) 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, (iii) copyrights (registered or unregistered)
and copyrightable works and registrations and applications for registration
thereof, (iv) mask works and registrations and applications for registration
thereof, (v) computer software, data, data bases and documentation thereof, (vi)
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), (vii) other
intellectual property rights, and (viii) copies and tangible embodiments thereof
(in whatever form or medium), in each case excluding unmodified mass market
software that is commercially available).

          "INVESTMENT" as applied to any Person means (i) any direct or indirect
purchase or other acquisition by such Person of any notes, obligations,
instruments, stock, securities or ownership interest (including partnership
interests and joint venture interests) of any other Person and (ii) any capital
contribution by such Person to any other Person.

          "LIENS" means any mortgage, pledge, security interest, encumbrance,
lien or charge of any kind (including, without limitation, any conditional sale
or other title retention agreement or lease in the nature thereof), any sale of
receivables with recourse against the Company or any Subsidiary, any filing or
agreement to file a financing statement as debtor under the Uniform Commercial
Code or any similar statute other than to reflect ownership by a third party of
property leased to the Company or any Subsidiaries under a lease which is not in
the nature of a conditional sale or title retention agreement, or any
subordination arrangement in favor of another Person (other than any
subordination arising in the ordinary course of business).

          "NET WORTH" shall mean, as of any date of determination, the excess of
the Company's total assets as of such date over the Company's total liabilities
as of such date, in each case as determined on a consolidated basis in
accordance with GAAP.

          "OPTION ADJUSTMENT DIVIDEND" has the meaning given to such term in the
Company's Certificate of Incorporation.

          "PERMITTED LIENS" means: (i) tax liens with respect to taxes not yet
due and payable or which are being contested in good faith by appropriate
proceedings and for which appropriate reserves have been established in
accordance with GAAP, consistently applied, on the books and financial
statements of the Company and its Subsidiaries; (ii) deposits or pledges made in
connection with, or to secure payment of, utilities or similar services,
workers' compensation, unemployment insurance, old age pensions or other social
security obligations; (iii) purchase money security interests in any property
acquired by the Company or any Subsidiary; (iv) liens or encumbrances with
respect to capital lease obligations that are permitted pursuant to subparagraph
1C(xvi) above, (v) interests or title of a lessor under any lease

                                     - 12 -
<Page>

permitted by this Agreement; (vi) mechanics', materialmen's or contractors'
liens or encumbrances or any similar lien or restriction for amounts not yet due
and payable; (vii) easements, rights-of-way, restrictions and other similar
charges and encumbrances not interfering with the ordinary conduct of the
business of the Company and its Subsidiaries or detracting from the value of the
assets of the Company and its Subsidiaries; and (viii) liens outstanding on the
date hereof which secure Indebtedness and which are described in the schedules
to the Recapitalization Agreement.

          "PERSON" means an individual, a partnership, a corporation, a limited
liability company, an association, a joint stock company, a trust, a joint
venture, an unincorporated organization and a governmental entity or any
department, agency or political subdivision thereof.

          "QUALIFIED PUBLIC OFFERING" has the meaning given to such term in the
Company's Certificate of Incorporation.

          "REGISTRATION AGREEMENT" has the meaning given to such term in the
Recapitalization Agreement.

          "RESTRICTED SECURITIES" means (i) the Series A Preferred issued
pursuant to the Recapitalization Agreement, (ii) the Common Stock issued upon
conversion of Series A Preferred and (iii) any securities issued with respect to
the securities referred to in clauses (i) or (ii) above by way of a stock
dividend or stock split or in connection with a combination of shares,
recapitalization, merger, consolidation or other reorganization. As to any
particular Restricted Securities, such securities shall cease to be Restricted
Securities when they have (a) been effectively registered under the Securities
Act and disposed of in accordance with the registration statement covering them
or (b) been distributed to the public through a broker, dealer or market maker
on a securities exchange or in the over-the-counter market pursuant to Rule 144
(or any similar provision then in force) under the Securities Act.

          "RESTRICTED STOCK AGREEMENTS" means those certain Amended and Restated
Restricted Stock Agreements, each dated as of the date hereof, by and between
the Company and each of Ned Bennett, James Gray and David Kalt.

          "SECURITIES ACT" means the Securities Act of 1933, as amended, or any
similar federal law then in force.

          "SECURITIES AND EXCHANGE COMMISSION" includes any governmental body or
agency succeeding to the functions thereof.

          "SECURITIES EXCHANGE ACT" means the Securities Exchange Act of 1934,
as amended, or any similar federal law then in force.

          "STOCKHOLDERS AGREEMENT" has the meaning given to such term in the
Recapitalization Agreement.

          "SUBSIDIARY" means, with respect to any Person, any corporation,
limited liability company, partnership, association or other business entity of
which (i) if a corporation, a

                                     - 13 -
<Page>

majority of the total voting power of shares of stock entitled (without regard
to the occurrence of any contingency) to vote in the election of directors,
managers or trustees thereof is at the time owned or controlled, directly or
indirectly, by that Person or one or more of the other Subsidiaries of that
Person or a combination thereof, or (ii) if a limited liability company,
partnership, association or other business entity, a majority of the partnership
or other similar ownership interest thereof is at the time owned or controlled,
directly or indirectly, by any Person or one or more Subsidiaries of that Person
or a combination thereof. For purposes hereof, a Person or Persons shall be
deemed to have a majority ownership interest in a limited liability company,
partnership, association or other business entity if such Person or Persons
shall be allocated a majority of limited liability company, partnership,
association or other business entity gains or losses or shall be or control any
managing director or general partner of such limited liability company,
partnership, association or other business entity.

          "TANGIBLE NET WORTH" shall mean, as of any date of determination, the
excess of the Company's total tangible assets as of such date over the Company's
total liabilities as of such date, in each case as determined on a consolidated
basis in accordance with GAAP.

          "UNDERLYING COMMON STOCK" means (i) the Common Stock issued or
issuable upon conversion of the Series A Preferred and (ii) any Common Stock or
other securities issued or issuable with respect to the securities referred to
in clause (i) above by way of stock dividend or stock split or in connection
with a combination of shares, recapitalization, merger, consolidation or other
reorganization. For purposes of this Agreement, any Person who holds Series A
Preferred shall be deemed to be the holder of the Underlying Common Stock
obtainable upon conversion of the Series A Preferred in connection with the
transfer thereof or otherwise regardless of any restriction or limitation on the
conversion of the Series A Preferred, such Underlying Common Stock shall be
deemed to be in existence, and such Person shall be entitled to exercise the
rights of a holder of Underlying Common Stock hereunder. As to any particular
shares of Underlying Common Stock, such shares shall cease to be Underlying
Common Stock when they have been (a) effectively registered under the Securities
Act and disposed of in accordance with the registration statement covering them,
(b) distributed to the public through a broker, dealer or market maker pursuant
to Rule 144 under the Securities Act (or any similar provision then in force) or
(c) repurchased by the Company or any Subsidiary.

          "WHOLLY-OWNED SUBSIDIARY" means, with respect to any Person, a
Subsidiary of which all of the outstanding capital stock or other ownership
interests are owned by such Person or another Wholly-Owned Subsidiary of such
Person (other than, in the case of a Subsidiary organized under the laws of a
foreign jurisdiction, any capital stock or other ownership interests that are
not so owned due solely to any foreign qualifying share or similar local law
requirements of such foreign jurisdiction).

          Section 3.   MISCELLANEOUS.

          3A.  EXPENSES. The Company shall pay, and hold each Investor and all
holders of Series A Preferred and Underlying Common Stock harmless against
liability for the payment of, (i) the reasonable fees and expenses incurred with
respect to any amendments or waivers (whether or not the same become effective)
under or in respect of this Agreement, the agreements contemplated hereby, or
the Certificate of Incorporation and (ii) stamp and other

                                     - 14 -
<Page>

taxes which may be payable in respect of the execution and delivery of this
Agreement or the agreements contemplated hereby or the issuance, delivery or
acquisition of any shares of Series A Preferred or any shares of Common Stock
issuable upon conversion of the Series A Preferred.

          3B.  REMEDIES. Each holder of Series A Preferred and Underlying
Common Stock shall have all rights and remedies set forth in this Agreement and
the Certificate of Incorporation and all rights and remedies which such holders
have been granted at any time under any other agreement or contract and all of
the rights which such holders have under applicable law. Any Person having any
rights under any provision of this Agreement shall be entitled to enforce such
rights specifically (without posting a bond or other security), to recover
damages by reason of any breach of any provision of this Agreement and to
exercise all other rights granted by law.

          3C.  CONSENT TO AMENDMENTS. Except as otherwise expressly provided
herein, the provisions of this Agreement may be amended and the Company may take
any action herein prohibited, or fail to perform any act herein required to be
performed by it, only if the Company has obtained the prior written consent of
the holders of a majority of the Underlying Common Stock. No other course of
dealing between the Company and the holder of any Series A Preferred or
Underlying Common Stock or any delay in exercising any rights hereunder or under
the Certificate of Incorporation shall operate as a waiver of any rights of any
such holders.

          3D.  SUCCESSORS AND ASSIGNS. Except as otherwise expressly provided
herein, all covenants and agreements contained in this Agreement by or on behalf
of any of the parties hereto shall bind and inure to the benefit of the
respective successors and assigns of the parties hereto whether so expressed or
not, and whether or not any express assignment has been made, the provisions of
this Agreement which are for any Investor's benefit as a Investor or holder of
Series A Preferred or Underlying Common Stock are also for the benefit of, and
enforceable by, any subsequent holder of such Series A Preferred or such
Underlying Common Stock.

          3E.  CAPITAL AND SURPLUS; SPECIAL RESERVES. The Company agrees that
the capital of the Company (as such term is used in Section 154 of the General
Corporation Law of Delaware) in respect of the Series A Preferred issued
pursuant to the Recapitalization Agreement shall be equal to the aggregate par
value of such shares and that it shall not increase the capital of the Company
with respect to any shares of the Company's capital stock at any time on or
after the date of this Agreement without the prior consent of the holders of a
majority of the outstanding Series A Preferred. The Company also agrees that it
shall not create any special reserves under Section 171 of the General
Corporation Law of Delaware without the prior written consent of the holders of
a majority of the outstanding Series A Preferred.

          3F.  GENERALLY ACCEPTED ACCOUNTING PRINCIPLES. Where any accounting
determination or calculation is required to be made under this Agreement, such
determination or calculation (unless otherwise provided) shall be made in
accordance with GAAP, consistently applied, except that if because of a change
in generally accepted accounting principles the Company would have to alter a
previously utilized accounting method or policy in order to remain in compliance
with GAAP, such determination or calculation shall continue to be made in
accordance with the Company's previous accounting methods and policies, unless
otherwise

                                     - 15 -
<Page>

directed by the Company's Board of Directors, including the affirmative vote of
the director elected by the holders of a majority of the outstanding Series A
Preferred.

          3G.  SEVERABILITY. Whenever possible, each provision of this
Agreement shall be interpreted in such manner as to be effective and valid under
applicable law, but if any provision of this Agreement is held to be prohibited
by or invalid under applicable law, such provision shall be ineffective only to
the extent of such prohibition or invalidity, without invalidating the remainder
of this Agreement.

          3H.  COUNTERPARTS. This Agreement may be executed simultaneously in
two or more counterparts, any one of which need not contain the signatures of
more than one party, but all such counterparts taken together shall constitute
one and the same Agreement.

          3I.  DESCRIPTIVE HEADINGS; INTERPRETATION. The descriptive headings
of this Agreement are inserted for convenience only and do not constitute a
substantive part of this Agreement. The use of the word "including" in this
Agreement shall be by way of example rather than by limitation.

          3J.  GOVERNING LAW. The corporate law of the State of Delaware shall
govern all issues and questions concerning the relative rights and obligations
of the Company and its stockholders. All other issues and questions concerning
the construction, validity, enforcement and interpretation of this Agreement and
the exhibits and schedules hereto shall be governed by, and construed in
accordance with, the laws of the State of Illinois, without giving effect to any
choice of law or conflict of law rules or provisions (whether of the State of
Illinois or any other jurisdiction) that would cause the application of the laws
of any jurisdiction other than the State of Illinois.

          3K.  NOTICES. All notices, demands or other communications to be
given or delivered under or by reason of the provisions of this Agreement shall
be in writing and shall be deemed to have been given when delivered personally
to the recipient, sent to the recipient by reputable overnight courier service
(charges prepaid) or mailed to the recipient by certified or registered mail,
return receipt requested and postage prepaid. Such notices, demands and other
communications shall be sent to each Investor at the address indicated on the
SCHEDULE OF INVESTORS attached hereto and to the Company at the address
indicated below:

          optionsXpress, Inc.
          39 South LaSalle Street

          Suite 220
          Chicago, Illinois 60603
          Telephone:   (888) 280-8020
          Telecopy:    (312) 629-5256
          Attention:   President

                                     - 16 -
<Page>

          WITH A COPY TO:
          (which shall not constitute notice to the Company)

          KMZ Rosenman
          525 West Monroe Street
          Suite 1600
          Chicago, Illinois 60661-3693
          Telephone:   (312) 902-5200
          Telecopy:    (312) 902-1061
          Attention:   Mathew Brown, Esq.

          or to such other address or to the attention of such other person as
the recipient party has specified by prior written notice to the sending party.

          3L.  NO STRICT CONSTRUCTION. The parties hereto have participated
jointly in the negotiation and drafting of this Agreement. In the event an
ambiguity or question of intent or interpretation arises, this Agreement shall
be construed as if drafted jointly by the parties hereto, and no presumption or
burden of proof shall arise favoring or disfavoring any party by virtue of the
authorship of any of the provisions of this Agreement. The parties hereto intend
that each covenant and agreement contained herein shall have independent
significance. If any party has breached any covenant or agreement contained
herein in any respect, the fact that there exists another covenant or agreement
relating to the same subject matter (regardless of the relative levels of
specificity) which such party has not breached shall not detract from or
mitigate the fact that such party is in breach of the first covenant or
agreement.

          3M.  COMPLETE AGREEMENT. This Agreement and the other agreements and
instruments referred to herein contain the complete agreement between the
parties hereto with respect to the subject matter hereof and thereof and
supersede any prior understandings, agreements and representations by or between
the parties hereto (whether written or oral) which may have related to the
subject matter hereof or thereof in any way.

                                    * * * * *

                                     - 17 -
<Page>

          IN WITNESS WHEREOF, the parties hereto have executed this Investor
Rights Agreement on the date first written above.

                                         OPTIONSXPRESS, INC.

                                         By:    /s/ DAVID KALT
                                                --------------------------------

                                         Its:   President

                                         SUMMIT VENTURES VI-A, L.P.

                                         By:    Summit Partners VI (GP), L.P.
                                         Its:   General Partner

                                         By:    Summit Partners VI (GP), LLC
                                         Its:   General Partner

                                         By:    /s/ BRUCE EVANS
                                                --------------------------------
                                                Member

                                         SUMMIT VENTURES VI-B, L.P.

                                         By:    Summit Partners VI (GP), L.P.
                                         Its:   General Partner

                                         By:    Summit Partners VI (GP), LLC
                                         Its:   General Partner

                                         By:    /s/ BRUCE EVANS
                                                --------------------------------
                                                Member

                                         SUMMIT VI ADVISORS FUND, L.P.

                                         By:    Summit Partners VI (GP), L.P.
                                         Its:   General Partner

                                         By:    Summit Partners VI (GP), LLC
                                         Its:   General Partner

                                         By:    /s/ BRUCE EVANS
                                                --------------------------------
                                                Member

<Page>

                                         SUMMIT VI ENTREPRENEURS FUND,
                                         L.P.

                                         By:    Summit Partners VI (GP), L.P.
                                         Its:   General Partner

                                         By:    Summit Partners VI (GP), LLC
                                         Its:   General Partner

                                         By:    /s/ BRUCE EVANS
                                                --------------------------------
                                                Member

                                         SUMMIT INVESTORS VI, L.P.

                                         By:    Summit Partners VI (GP), L.P.
                                         Its:   General Partner

                                         By:    Summit Partners VI (GP), LLC
                                         Its:   General Partner

                                         By:    /s/ BRUCE EVANS
                                                --------------------------------
                                                Member

<Page>

                              SCHEDULE OF INVESTORS

Summit Ventures VI-A, L.P.
Summit Ventures VI-B, L.P.
Summit VI Advisors Fund, L.P.
Summit VI Entrepreneurs Fund, L.P.
Summit Investors VI, L.P.

c/o Summit Partners, L.P.
222 Berkeley Street
18th Floor
Boston, Massachusetts 02116
Telephone:   (617) 824-1000
Telecopy:    (617) 824-1100
Attention:   Mr. Bruce R. Evans

WITH A COPY TO:
(which shall not constitute notice to the Investors)

Kirkland & Ellis LLP
200 East Randolph Drive
Chicago, Illinois 60601
Telephone:   (312) 861-2000
Telecopy:    (312) 861-2200
Attention:   Ted H. Zook, P.C.

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