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Exhibit 10.2

VOTING AGREEMENT

        THIS VOTING AND PROXY AGREEMENT (this "Agreement") is made and entered
into as of April 13, 2008 by and among Cobra Green LLC, a Delaware limited
liability company ("Buyer"), and the persons executing this Agreement as
"Stockholders" on the signature page hereto (each, a "Stockholder" and
collectively, the "Stockholders").

RECITALS

        WHEREAS, concurrently herewith, Buyer, Cobra Acquisition Corp., a
Delaware corporation and wholly-owned subsidiary of Buyer ("Merger Sub"), and
Clayton Holdings, Inc., a Delaware corporation ("Seller"), have entered into an
Agreement and Plan of Merger (as amended from time to time, the "Merger
Agreement") pursuant to which Buyer will acquire Seller by merging Merger Sub
with and into Seller (the "Merger");

        WHEREAS, as of the date hereof, each Stockholder is the record and
Beneficial Owner of, and has the sole right to vote and dispose of, that number
of shares of Seller Common Stock set forth below such Stockholder's name in the
signature page hereto;

        WHEREAS, obtaining Seller Stockholders' Approval is a condition to the
consummation of the transactions contemplated by the Merger Agreement; and

        WHEREAS, as an inducement to Buyer and Merger Sub to enter into the
Merger Agreement and incurring the obligations therein, Buyer has required that
each Stockholder enter into this Agreement.

        NOW, THEREFORE, in consideration of the foregoing, the mutual covenants
and agreements set forth herein, and other good and valuable consideration, the
receipt and sufficiency of which is hereby acknowledged, the parties hereto
agree as follows:

I. CERTAIN DEFINITIONS

        Section 1.1    Capitalized Terms.    Capitalized terms used in this
Agreement and not defined herein have the meanings ascribed to such terms in the
Merger Agreement.

        Section 1.2    Other Definitions.    For the purposes of this Agreement:

        (a)   "Beneficial Owner" or "Beneficial Ownership" with respect to any
securities means having "beneficial ownership" of such securities (as determined
pursuant to Rule 13d-3 under the Exchange Act).

        (b)   "Owned Shares" means, with respect to each Stockholder, the Shares
Beneficially Owned by such Stockholder as of the date of this Agreement and set
forth below its name on the signature page hereto and, subject to the limitation
set forth in Section 2.2 of this Agreement, any Shares acquired by such
Stockholder after the date of this Agreement.

        (c)   "Shares" means shares of common stock, $0.01 par value per share,
of Seller and all shares or other voting securities into which such shares of
common stock may be reclassified, sub-divided, consolidated or converted and any
rights and benefits arising therefrom, including any dividends or distributions
of securities which may be declared in respect of such common stock and entitled
to vote in respect of the matters contemplated by Article II.

        (d)   "Transfer" means, with respect to a security, the sale, grant,
assignment, transfer, pledge, encumbrance or other disposition of such security
or the Beneficial Ownership thereof (including by operation of Law), or the
entry into any Contract to effect any of the foregoing, including, for

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purposes of this Agreement, the transfer or sharing of any voting power of such
security or other rights in or of such security.

II. AGREEMENT TO VOTE

        Section 2.1    Agreement to Vote.    Subject to the terms and conditions
hereof, each Stockholder irrevocably and unconditionally agrees that from and
after the date hereof and until the earliest to occur of (i) the Effective Time
and (ii) the termination of the Merger Agreement in accordance with its terms
(such earlier occurrence being the "Expiration Time"), at any meeting (whether
annual or special, and at each adjourned or postponed meeting) of the Seller
Stockholders, however called, each Stockholder will (x) appear at such meeting
or otherwise cause its Owned Shares to be counted as present thereat for
purposes of calculating a quorum and (y) vote, or instruct to be voted, all of
such Stockholder's Owned Shares (A) in favor of the adoption of the Merger
Agreement and the approval of the transactions contemplated thereby, including
the Merger, (B) in favor of the approval of any other matter that is required by
applicable Law or a Governmental Authority to be approved by the Seller
Stockholders to consummate the transactions contemplated by the Merger
Agreement, including the Merger, (C) against any Acquisition Proposal other than
the Merger or the Merger Agreement, and without regard to the terms of such
Acquisition Proposal, (D) against any proposal made in opposition to, or in
competition or inconsistent with, the Merger or the Merger Agreement, including
the adoption thereof or the consummation thereof, (E) against any action or
agreement that may reasonably be expected to result in any condition to the
consummation of the Merger set forth in Article VII of the Merger Agreement not
being fulfilled, and (F) against any agreement, amendment of any agreement
(including the Seller Charter or the Amended and Restated Bylaws of the Seller)
or any other action that may reasonably be expected to impede, interfere with,
delay, postpone or attempt to discourage the consummation of the transactions
contemplated by the Merger Agreement, including the Merger, or may reasonably be
expected to result in a breach of any of the covenants, representations,
warranties or other obligations or agreements of Seller, Buyer or Merger Sub
under the Merger Agreement, which may reasonably be expected to materially and
adversely affect Seller, Buyer or Merger Sub or their respective abilities to
consummate the transactions contemplated by the Merger Agreement within the time
periods contemplated thereby.

        Section 2.2    Additional Shares.    Each Stockholder hereby agrees,
while this Agreement is in effect, to promptly notify Seller of the number of
any new Shares with respect to which Beneficial Ownership is acquired by such
Stockholder, if any, after the date hereof and before this Agreement is
terminated pursuant to Section 5.1. Any such Shares shall automatically become
subject to the terms of this Agreement as though owned by such Stockholder as of
the date hereof; provided, however that the terms of this Agreement shall not
apply to any Shares acquired by the Stockholders following the date hereof
which, when added to the aggregate number of Shares then Beneficially Owned by
the Stockholders, would provide the Stockholders with Beneficial Ownership in
the aggregate of more than 40% of the Seller's then outstanding Shares (and for
the avoidance of doubt, such acquired Shares shall not be deemed Owned Shares
for purposes of this Agreement).

        Section 2.3    Restrictions on Transfer, Etc.    Each Stockholder
agrees, from the date hereof until this Agreement is terminated pursuant to
Section 5.1, not to (i) directly or indirectly Transfer any Owned Shares,
(ii) tender any Owned Shares into any tender or exchange offer or otherwise, or
(iii) grant any proxy with respect to such Stockholder's Owned Shares, deposit
such Stockholder's Owned Shares into a voting trust, enter into a voting
agreement with respect to any of such Stockholder's Owned Shares or otherwise
restrict the ability of such Stockholder freely to exercise all voting rights
with respect thereto. Any action attempted to be taken in violation of the
preceding sentence will be null and void.

        Section 2.4    Proxies.    Each Stockholder hereby revokes any and all
previous proxies granted with respect to such Stockholder's Owned Shares. Each
Stockholder will, if requested by Seller, (i) with respect to Owned Shares for
which it is the record owner, grant a proxy appointing Eugene A. Gorab

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and Barry P. Marcus collectively, but each with full power of substitution, as
such Stockholder's attorney-in-fact and proxy, for and in such Stockholder's
name, to be counted as present and to vote in favor of the adoption of the
Merger Agreement and the approval of the transactions contemplated thereby,
including the Merger, and (ii) with respect to Owned Shares for which it is not
the record owner, obtain a "legal proxy" from the record owner to vote in favor
of the adoption of the Merger Agreement and the approval of the transactions
contemplated thereby, including the Merger. Any proxy granted by each
Stockholder pursuant to this Section 2.4 shall be automatically revoked upon
termination of this Agreement in accordance with its terms.

III. REPRESENTATIONS AND WARRANTIES

        Section 3.1    Representations and Warranties of Stockholders.    Each
Stockholder represents and warrants to Buyer as follows:

        (a)   such Stockholder has the requisite capacity and all necessary
power and authority to execute and deliver this Agreement and to perform its
obligations hereunder;

        (b)   this Agreement has been duly executed and delivered by such
Stockholder and the execution, delivery and performance of this Agreement by
such Stockholder and the consummation of the transactions contemplated hereby
have been duly authorized by all necessary action on the part of such
Stockholder;

        (c)   assuming the due authorization, execution and delivery of this
Agreement by Buyer, this Agreement constitutes the valid and binding agreement
of such Stockholder enforceable against such Stockholder in accordance with its
terms;

        (d)   the execution and delivery of this Agreement by such Stockholder
does not conflict with or violate any Law or agreement binding upon it, nor
require any consent, notification, regulatory filing or approval; and

        (e)   except for restrictions in favor of Buyer pursuant to this
Agreement and except for such transfer restrictions of general applicability as
may be provided under the Securities Act of 1933, as amended, and the "blue sky"
Laws of the various States of the United States, such Stockholder owns,
beneficially and of record, all of such Stockholder's Owned Shares free and
clear of any proxy, voting restriction or other lien and has sole voting power
and sole power of disposition with respect to such Stockholder's Owned Shares,
and no Person other than such Stockholder has any right to direct or approve the
voting or disposition of any of such Stockholder's Owned Shares.

IV. ADDITIONAL COVENANTS OF THE STOCKHOLDERS AND THE COMPANY

        Section 4.1    Disclosure.    Each Stockholder hereby authorizes Buyer,
Merger Sub and Seller to publish and disclose in any announcement or disclosure
required by the SEC, including the Proxy Statement, such Stockholder's identity
and ownership of the Owned Shares and the nature of such Stockholder's
obligation under this Agreement.

        Section 4.2    Non-Interference; Further Assurances.    Each Stockholder
agrees that prior to the termination of this Agreement, such Stockholder shall
not take any action that may reasonably be expected to make any representation
or warranty of such Stockholder contained herein untrue or incorrect or may
reasonably be expected to have the effect of preventing, impeding, interfering
with or adversely affecting the performance by such Stockholder of its
obligations under this Agreement. Each Stockholder agrees, without further
consideration but at Buyer's expense, to execute and deliver such additional
documents and to take such further actions as necessary or reasonably requested
by Buyer to confirm and assure the rights and obligations set forth in this
Agreement or to consummate the transactions contemplated by this Agreement.

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        Section 4.3    No Solicitation.    

        (a)   Upon execution of this Agreement, each Stockholder shall and shall
cause its Affiliates and Representatives to cease immediately and cause to be
terminated any and all existing activities, discussions or negotiations with any
Person conducted heretofore with respect to, or that may reasonably be expected
to lead to, an Acquisition Proposal.

        (b)   No Stockholder shall, and each Stockholder shall cause its
Affiliates and its Representatives not to, directly or indirectly, (i) initiate,
solicit, or knowingly encourage the submission of any inquiries, proposals or
offers or any other efforts or attempts that constitute or may reasonably be
expected to lead to, any Acquisition Proposal, (ii) engage or participate in or
knowingly facilitate any discussions or negotiations regarding, or furnish any
non-public information to any Person (other than Buyer or Merger Sub) in
connection with any inquiries, proposals or offers or any other efforts or
attempts that constitute or may reasonably be expected to lead to, any
Acquisition Proposal or (iii) enter into any letter of intent, merger agreement,
agreement in principle, share purchase agreement, asset purchase agreement or
share exchange agreement, option agreement or similar agreement relating to an
Acquisition Proposal, or enter into any agreement or agreement in principle
requiring any Stockholder to abandon, terminate or fail to consummate the
transactions contemplated hereby or breach its obligations hereunder or resolve,
propose or agree to do any of the foregoing.

        Section 4.4    Waiver of Appraisal Rights.    To the extent permitted by
applicable Law, each Stockholder hereby waives any rights of appraisal of rights
of dissent from the Merger that Stockholder may have.

V. TERMINATION

        Section 5.1    Termination.    Subject to Section 5.2, this Agreement
(i) may be terminated by the mutual written consent of the parties hereto or
(ii) shall terminate without further action at the Expiration Time.

        Section 5.2    Effect of Termination.    Upon termination of this
Agreement, the rights and obligations of all the parties will terminate and
become void without further action by any party except for the provisions of
this Section 5.2 and Article VI of this Agreement, which will survive such
termination. For the avoidance of doubt, the termination of this Agreement shall
not relieve any party of liability for any willful breach of this Agreement
prior to the time of termination.

VI. GENERAL

        Section 6.1    Notices.    Any notice, request, instruction or other
communication under this Agreement will be in writing and delivered by hand or
overnight courier service or by facsimile, (i) if to a Stockholder, to the
address set forth below such Stockholder's name on the signature page hereto,
and (ii) if to Buyer, to the address set forth in Section 9.3 of the Merger
Agreement, or to such other Persons, addresses or facsimile numbers as may be
designated in writing by the Person entitled to receive such communication as
provided above. Each such communication will be effective (A) if delivered by
hand or overnight courier service, when such delivery is made at the address
specified in this Section 6.1, or (B) if delivered by facsimile, when such
facsimile is transmitted to the facsimile number specified in this Section 6.1
and appropriate confirmation is received.

        Section 6.2    No Third Party Beneficiaries, Etc.    This Agreement is
not intended to confer any rights or remedies upon any Person other than the
parties to this Agreement, or to make any Stockholder responsible for any of
Buyer's or Merger Sub's obligations under the Merger Agreement.

        Section 6.3    Severability.    The provisions of this Agreement are
severable and the invalidity or unenforceability of any provision will not
affect the validity or enforceability of the other provisions of

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this Agreement. If any provision of this Agreement, or the application of that
provision to any Person or any circumstance, is invalid or unenforceable, (i) a
suitable and equitable provision will be substituted for that provision in order
to carry out, so far as may be valid and enforceable, the intent and purpose of
the invalid or unenforceable provision and (ii) the remainder of this Agreement
and the application of that provision to other Persons or circumstances will not
be affected by such invalidity or unenforceability, nor will such invalidity or
unenforceability affect the validity or enforceability of that provision, or the
application of that provision, in any other jurisdiction.

        Section 6.4    Assignment.    Neither this Agreement nor any right,
interest or obligation hereunder may be assigned by any party hereto, in whole
or part (whether by operation of Law or otherwise), without the prior written
consent of the other parties hereto and any attempt to do so will be null and
void.

        Section 6.5    Successors.    This Agreement will inure to the benefit
of and be binding upon the parties hereto and their respective successors and
permitted assigns.

        Section 6.6    Interpretation.    The headings in this Agreement are for
reference only and do not affect the meaning or interpretation of this
Agreement. Definitions apply equally to both the singular and plural forms of
the terms defined. Whenever the context may require, any pronoun includes the
corresponding masculine, feminine and neuter forms. All references in this
Agreement to Articles and Sections refer to Articles and Sections of this
Agreement unless the context requires otherwise. The words "include," "includes"
and "including" are not limiting and will be deemed to be followed by the phrase
"without limitation." The phrases "herein," "hereof," "hereunder" and words of
similar import shall be deemed to refer to this Agreement as a whole and not to
any particular provision of this Agreement. The word "or" shall be inclusive and
not exclusive unless the context requires otherwise. Unless the context requires
otherwise, any agreements, documents, instruments or Laws defined or referred to
in this Agreement will be deemed to mean or refer to such agreements, documents,
instruments or Laws as from time to time amended, modified or supplemented,
including (i) in the case of agreements, documents or instruments, by waiver or
consent and (ii) in the case of Laws, by succession of comparable successor
statutes. All references in this Agreement to any particular Law will be deemed
to refer also to any rules and regulations promulgated under that Law.
References to a Person will refer to its predecessors and successors and
permitted assigns.

        Section 6.7    Amendments.    This Agreement may not be amended except
by written agreement signed by all of the parties to this Agreement.

        Section 6.8    Extension; Waiver.    At any time prior to the Effective
Time, Buyer, on the one hand, and the Stockholders, on the other hand, may
(i) extend the time for the performance of any of the obligations of the other
party, (ii) waive any inaccuracies in the representations and warranties of the
other party contained in this Agreement or in any document delivered under this
Agreement or (iii) unless prohibited by applicable Laws, waive compliance with
any of the covenants or conditions contained in this Agreement. Any agreement on
the part of a party to any extension or waiver will be valid only if set forth
in an instrument in writing signed by such party. The failure of any party to
assert any of its rights under this Agreement or otherwise will not constitute a
waiver of such rights.

        Section 6.9    Fees and Expenses.    Except as expressly provided in
this Agreement, each party is responsible for its own fees and expenses
(including the fees and expenses of financial consultants, investment bankers,
accountants and counsel) in connection with the entry into of this Agreement and
the consummation of the transactions contemplated hereby.

        Section 6.10    Entire Agreement.    This Agreement constitutes the
entire agreement and supersedes all other prior agreements, understandings,
representations and warranties, both written and oral, among the parties to this
Agreement with respect to the subject matter of this Agreement.

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        Section 6.11    Rules of Construction.    The parties to this Agreement
have been represented by counsel during the negotiation and execution of this
Agreement and waive the application of any Laws or rule of construction
providing that ambiguities in any agreement or other document will be construed
against the party drafting such agreement or other document.

        Section 6.12    Remedies Cumulative.    Except as otherwise provided in
this Agreement, any and all remedies expressly conferred upon a party to this
Agreement will be cumulative with, and not exclusive of, any other remedy
contained in this Agreement, at law or in equity. The exercise by a party to
this Agreement of any one remedy will not preclude the exercise by it of any
other remedy.

        Section 6.13    Counterparts; Effectiveness; Execution.    This
Agreement may be executed in any number of counterparts, all of which are one
and the same agreement. This Agreement will become effective and binding upon
each Stockholder when executed by such Stockholder and Seller. This Agreement
may be executed by facsimile signature by any party and such signature is deemed
binding for all purposes hereof, without delivery of an original signature being
thereafter required.

        Section 6.14    Specific Performance.    The parties to this Agreement
agree that irreparable damage would occur in the event that any of the
provisions of this Agreement were not performed in accordance with their
specific terms or were otherwise breached. It is accordingly agreed that the
parties to this Agreement will be entitled to an injunction or injunctions to
prevent breaches of this Agreement and to enforce specifically the terms and
provisions of this Agreement in any court of the United States or any state
having jurisdiction, this being in addition to any other remedy to which they
are entitled at law or in equity.

        Section 6.15    Governing Law; Jurisdiction and Venue.    This Agreement
shall be governed by and construed in accordance with the Laws of the State of
Delaware without regard to its rules of conflict of laws. Each of Stockholder
and Buyer hereby irrevocably and unconditionally consents to submit to the
exclusive jurisdiction of the courts of the State of Delaware and of the United
States of America located in the State of Delaware (the "Delaware Courts") for
any litigation arising out of or relating to this Agreement and the transactions
contemplated hereby (and agrees not to commence any litigation relating thereto
except in such courts), waives any objection to the laying of venue of any such
litigation in the Delaware Courts and agrees not to plead or claim in any
Delaware Court that such litigation brought therein has been brought in any
inconvenient forum. Each of the parties hereto agrees, (a) to the extent such
party is not otherwise subject to service of process in the State of Delaware,
to appoint and maintain an agent in the State of Delaware as such party's agent
for acceptance of legal process, and (b) that service of process may also be
made on such party by prepaid certified mail with a proof of mailing receipt
validated by United States Postal Service constituting evidence of valid
service. Service made pursuant to (a) or (b) above shall have the same legal
force and effect as if served upon such party personally within the State of
Delaware.

        Section 6.16    WAIVER OF JURY TRIAL.    THE PARTIES IRREVOCABLY AND
UNCONDITIONALLY WAIVE ANY RIGHT THEY MAY HAVE TO A TRIAL BY JURY IN RESPECT OF
ANY LEGAL ACTION ARISING OUT OF OR RELATING TO THIS AGREEMENT OR THE
TRANSACTIONS CONTEMPLATED BY THIS AGREEMENT.

        Section 6.17    Action in Stockholder Capacity Only.    The parties
acknowledge that this Agreement is entered into by each Stockholder solely in
such Stockholder's capacity as the Beneficial Owner of such Stockholder's Owned
Shares and nothing in this Agreement, including the restrictions in Section 4.3,
shall in any way restrict or limit any action taken by any Affiliates or
Representatives of such Stockholder in his capacity as a director or officer of
the Company (but solely in such capacities as director or officer of the
Company).

[Remainder of page intentionally left blank. Signature Page Follows.]

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        IN WITNESS WHEREOF, each party hereto has caused this Agreement to be
signed as of the date first above written.

    COBRA GREEN LLC
 
 
By:
/s/  EUGENE A. GORAB      

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      Name: Eugene A. Gorab       Title: President
 
 
TA IX L.P.
 
 
By:
TA Associates IX LLC, its General Partner
 
 
By:
TA Associates, Inc., its Manager
 
 
By:
/s/  ROGER B. KAFKER      

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      Name: Roger B. Kafker       Its: Managing Director       Owned Shares:
6,297,362
 
 
TA/ATLANTIC AND PACIFIC IV L.P.
 
 
By:
TA Associates AP IV L.P., its General Partner
 
 
By:
TA Associates, Inc., its General Partner
 
 
By:
/s/  ROGER B. KAFKER      

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      Name: Roger B. Kafker       Its: Managing Director       Owned Shares:
1,484,323
 
 
TA STRATEGIC PARTNERS FUND A L.P.
 
 
By:
TA Associates SPF L.P., its General Partner
 
 
By:
TA Associates, Inc., its General Partner
 
 
By:
/s/  ROGER B. KAFKER      

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      Name: Roger B. Kafker       Its: Managing Director       Owned Shares:
128,937

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TA STRATEGIC PARTNERS FUND B L.P.
 
 
By:
TA Associates SPF L.P., its General Partner
 
 
By:
TA Associates, Inc., its General Partner
 
 
By:
/s/  ROGER B. KAFKER      

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      Name: Roger B. Kafker       Its: Managing Director       Owned Shares:
23,142
 
 
TA INVESTORS II, L.P.
 
 
By:
TA Associates, Inc., its General Partner
 
 
By:
/s/  ROGER B. KAFKER      

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      Name: Roger B. Kafker       Its: Managing Director       Owned Shares:
130,327
 
 
TA SUBORDINATED DEBT FUND, L.P.
 
 
By:
TA Associates SDF LLC, its General Partner
 
 
By:
TA Associates, Inc., its Manager
 
 
By:
/s/  ROGER B. KAFKER      

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      Name: Roger B. Kafker       Its: Managing Director       Owned Shares:
219,136

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QuickLinks

Exhibit 10.2

VOTING AGREEMENT
RECITALS
I. CERTAIN DEFINITIONS
II. AGREEMENT TO VOTE
III. REPRESENTATIONS AND WARRANTIES
IV. ADDITIONAL COVENANTS OF THE STOCKHOLDERS AND THE COMPANY
V. TERMINATION
VI. GENERAL