Document:

EX-10.21

AMENDMENT NO. 1 TO 

AMENDED AND RESTATED EXECUTIVE EMPLOYMENT AGREEMENT

     THIS AMENDMENT NO. 1 TO AMENDED AND RESTATED EXECUTIVE EMPLOYMENT AGREEMENT (this
“Amendment”) is made this 31st day of December, 2008 between DealerTrack Holdings, Inc. a
Delaware corporation (the “Company”), and Robert Cox, (“Executive”).

     WHEREAS, the Company and Executive entered into the Amended and Restated Senior Executive
Employment Agreement, dated as of August 8, 2007 (the “Employment Agreement”); and

     WHEREAS, the parties now desire to amend the Employment Agreement by modifying the terms
thereof as required by Section 409A of the Internal Revenue Code of 1986, as amended.

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

     1. Amendments.

          (a) Effective immediately, Section 5(d) of the Employment Agreement is deleted in its entirety
and shall have no further force or effect (herein referred to as the “Original Release
Provision”):

“Notwithstanding anything to the contrary contained herein, no severance
payments required hereunder shall be made by Employer until such time as
Executive shall execute a general release for the benefit of Employer and
its affiliates in a form satisfactory to Employer. Such general release
shall not apply to (i) Executive’s rights under any Stock Incentive Plan
award agreements or (ii) Executive’s rights, as applicable, to
indemnification under Employer’s charter or bylaws, any indemnification
agreement or applicable law.”

          (b) Effective immediately, the following paragraph is inserted in place of and replaces the
Original Release Provision in its entirety:

“Notwithstanding anything to the contrary contained herein, no severance
payments required hereunder shall be made by Employer unless Executive
executes and delivers a general release for the benefit of Employer and its
affiliates in a form satisfactory to Employer, which release shall be
executed and delivered (and not revoked) promptly (and in no event more than
50 days following the Executive’s termination). Such general release shall
not apply to (i) Executive’s rights under any Stock Incentive Plan award
agreements or (ii) Executive’s rights, as applicable, to indemnification
under Employer’s charter or bylaws, any indemnification agreement or
applicable law.”

 

 

          (c) Effective immediately, the Employment Agreement is hereby amended to add the following
Section 24:

               “Section 24. Section 409A

                    (a) For purposes of Section 5(c)(1) of this Agreement, a “termination of employment”
shall only occur if there has been a “separation from service” within the meaning of Treasury
Regulation Section 1.409A-1(h)(1), without regard to the optional alternative definitions available
thereunder.

                    (b) It is intended that any amounts payable under this Agreement and the Employer’s and
Executive’s exercise of authority or discretion hereunder shall comply with and avoid the
imputation of any tax, penalty or interest under Section 409A. This Agreement shall be construed
and interpreted consistent with that intent.”

     2. Other Terms Unmodified. Except as expressly modified hereby, the Employment
Agreement remains unmodified.

     3. Counterparts. This Amendment may be executed in any number of counterparts, each of
which will be deemed an original, but all of which together will constitute one and the same
instrument. Facsimile copies shall have the same effect as originals.

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     IN WITNESS WHEREOF, the parties hereto have executed and delivered this Amendment as of the
date first written above.

	 	 	 	 	 
	 	 	EXECUTIVE:
	 
	 	 	 	 
	 	 	 
	 	 	Robert Cox
	 

	 	Date:	 	 
	 
	 	 	 	 
	 	 	COMPANY:
	 
	 	 	 	 
	 

	 	By:
	 	 
	 

	 	 	 	 
	 
	 	 	 	 
	 

	 	Name:	 	 
	 

	 	 	 	 
	 
	 	 	 	 
	 

	 	Title:	 	 
	 

	 	 	 	 
	 
	 	 	 	 
	 

	 	Date:EX-10.31

TO RESTRICTED STOCK UNIT AWARD GRANT NOTICE

DEALERTRACK HOLDINGS, INC. RESTRICTED STOCK UNIT AWARD AGREEMENT

     Pursuant to the Restricted Stock Unit Award Grant Notice (the “Grant Notice”) to which this
Restricted Stock Award Agreement (the “Agreement”) is attached, DealerTrack Holdings, Inc., a
Delaware corporation (the “Company”) has granted to Participant the number of Restricted Stock
Units under the Amended and Restated 2005 Incentive Award Plan, as amended from time to time (the
“Plan”), as set forth in the Grant Notice.

ARTICLE I

GENERAL

     1.1 Definitions. All capitalized terms used in this Agreement but not defined in this
Agreement shall have the meanings ascribed to them in the Plan and the Grant Notice.

ARTICLE II.

AWARD OF RESTRICTED STOCK UNITS

     2.1 Award of Restricted Stock Units.

          (a) Award. Subject to the terms of this Agreement, the Company hereby grants to the
Participant an Award (as defined below) with respect the number of Restricted Stock Units set forth
in the Grant Notice (subject to adjustment as provided in Section 11.1 of the Plan) (the “Award”).
As used herein, the term “Restricted Stock Unit” shall mean a non-voting unit of measurement which
is deemed for bookkeeping purposes to be equivalent to one outstanding share of the Company’s Stock
(subject to adjustment as provided in Section 11.1 of the Plan) solely for purposes of the Plan and
this Agreement. The Stock Units shall not be treated as property or a trust fund of any kind.

          (b) Plan. The Award granted hereunder is subject to the terms and provisions of the
Plan, including without limitation, Article 11 thereof.

     2.2 Restrictions.

          (a) Forfeiture. Any Award which is not vested upon the Participant’s termination of
employment shall thereupon be terminated and forfeited immediately and without any further action
by the Company and without any consideration by the Company.

          (b) Vesting and Lapse of Restrictions. Subject to Sections 2.2(a), 2.2(c) and 2.2(d),
the Award shall vest in accordance with the vesting schedule set forth on the Grant Notice or any
other written agreement between the Company or any of its Subsidiaries, on the one hand, and
Participant, on the other hand.

          (c) Acceleration of Vesting. Notwithstanding Sections 2.2(a) and 2.2(b), pursuant to
Section 11.3 of the Plan, the Award shall become fully vested and all Restrictions applicable to
such Award shall lapse in the event of a Change in Control, in connection with which the successor
corporation does not assume the Award or substitute an equivalent right for the Award. Should the
successor

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corporation assume the Award or substitute an equivalent right, then no such acceleration
shall apply (unless otherwise determined by the Committee pursuant to the terms of the Plan).

          (d) Continuance of Employment. The vesting schedule requires continued employment or
service through each applicable vesting date as a condition to the vesting of the applicable
installment of the Award and the rights and benefits under this Agreement. Employment or service
for only a portion of the vesting period, even if a substantial portion, will not entitle the
Participant to any proportionate vesting or avoid or mitigate a termination of rights and benefits
upon or following a termination of employment or services. Nothing contained in this Agreement or
the Plan constitutes an employment or service commitment by the Company, affects the Participant’s
status as an employee at will who is subject to termination without Cause, confers upon the
Participant any right to remain employed by or in service to the Company or any Subsidiary,
interferes in any way with the right of the Company or any Subsidiary at any time to terminate such
employment or services, or affects the right of the Company or any Subsidiary to increase or
decrease the Participant’s other compensation or benefits. Nothing in this paragraph, however, is
intended to adversely affect any independent contractual right of the Participant without his
consent thereto.

          (e) Limitations on Rights Associated with Restricted Stock Units. The Participant
shall have no rights as a stockholder of the Company, no dividend rights and no voting rights with
respect to the Restricted Stock Units and any Stock underlying or issuable in respect of such
Restricted Stock Units until such Stock is actually issued to and held of record by the
Participant. No adjustments will be made for dividends or other rights of a holder for which the
record date is prior to the issuance of the stock certificate.

          (f) Restrictions on Transfer. Neither the Award, nor any interest therein or amount
or shares payable in respect thereof may be sold, assigned, transferred, pledged or otherwise
disposed of, alienated or encumbered, either voluntarily or involuntarily. The transfer
restrictions in the preceding sentence shall not apply to (a) transfers to the Company, or (b)
transfers by will or the laws of descent and distribution.

ARTICLE III.

OTHER PROVISIONS

     3.1 Timing and Manner of Payment of Restricted Stock Units. On or as soon as
administratively practical following each vesting of the applicable portion of the total Award
pursuant to Article II hereof or Article 11 of the Plan (and in all events not later than 60 days
after the applicable vesting date), the Company shall deliver to the Participant a number of shares
of Stock (either by delivering one or more certificates for such Stock or by entering such Stock in
book entry form, as determined by the Company in its discretion) equal to the number of Restricted
Stock Units subject to the Award that vest on the applicable vesting date, unless such Restricted
Stock Units terminate prior to vesting pursuant to Sections 3(b) and 3(c) above. The Company’s
obligation to deliver Shares is subject to the condition precedent that the Participant or other
person entitled under the Plan to receive any Stock with respect to the vested Restricted Stock
Units deliver to the Company any representations or other documents or assurances required pursuant
to Section 10.5 of the Plan.

     3.2 Adjustments upon Specified Events. Upon the occurrence of certain events relating
to the Company’s stock contemplated by Section 11.1 of the Plan (including, without limitation, an
extraordinary cash dividend on such stock), the Committee shall make adjustments in accordance with
such section in the number of Restricted Stock Units then outstanding and the number and kind of
securities that may be issued in respect of the Award.

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     3.3 Tax Withholding. Subject to Section 15.3 of the Plan, upon any distribution of
Stock in respect of the Restricted Stock Units, the Committee may in its discretion reduce the
number of shares to be delivered by (or otherwise reacquire) the appropriate number of whole
shares, valued at their then Fair Market Value, to satisfy any withholding obligations of the
Company or its Subsidiaries with respect to such distribution of shares at the minimum applicable
withholding rates. In the event that the Company does not satisfy such withholding obligations by
such reduction of shares, or in the event of a cash payment or any other withholding event in
respect of the Restricted Stock Units, the Company (or a Subsidiary) shall be entitled to require a
cash payment by or on behalf of the Participant and/or to deduct from any compensation payable to
the Participant any sums required by federal, state or local tax law to be withheld with respect to
such distribution or payment.

     3.4 Governing Law. The laws of the State of Delaware shall govern the
interpretation, validity, administration, enforcement and performance of the terms of this
Agreement regardless of the law that might be applied under principles of conflicts of laws.

     3.5 Conformity to Securities Laws. The Participant acknowledges that the Plan and
this Agreement are intended to conform to the extent necessary with all provisions of the
Securities Act of 1933, as amended, and the Securities Exchange Act of 1934, as amended (the
“Exchange Act”), and any and all regulations and rules promulgated thereunder by the Securities and
Exchange Commission, including without limitation Rule 16b-3 under the Exchange Act.
Notwithstanding anything herein to the contrary, the Plan shall be administered, and the Awards are
granted, only in such a manner as to conform to such laws, rules and regulations. To the extent
permitted by applicable law, the Plan and this Agreement shall be deemed amended to the extent
necessary to conform to such laws, rules and regulations.

     3.6 Amendment, Suspension and Termination. The Awards may be wholly or partially
amended or otherwise modified, suspended or terminated at any time or from time to time by the
Committee or the Board, provided, that, except as may otherwise be provided by the Plan, neither
the amendment, suspension nor termination of this Agreement shall, without the consent of the
Participant, alter or impair any rights or obligations under any Award.

     3.7 Notices. Notices required or permitted hereunder shall be given in writing and
shall be deemed effectively given upon personal delivery or upon deposit in the United States mail
by certified mail, with postage and fees prepaid, addressed to the Participant to his address shown
in the Company records, and to the Company at its principal executive office.

     3.8 Construction. It is intended that the terms of the Award will not result in the
imposition of any tax liability pursuant to Section 409A of the Code. This Agreement shall be
construed and interpreted consistent with that intent.

     3.9 Successors and Assigns. The Company may assign any of its rights under this
Agreement to single or multiple assignees, and this Agreement shall inure to the benefit of the
successors and assigns of the Company. Subject to the restrictions on transfer herein set forth,
this Agreement shall be binding upon Participant and his or her heirs, executors, administrators,
successors and assigns.

     The Participant represents that he has read this Agreement and the Plan and is familiar with
the terms and provisions of each. The Participant acknowledges that the Award is issued pursuant
to, and is subject to the terms and conditions of, the Plan, and the Participant will be bound by
the terms of the Plan as if it were set forth verbatim in this Agreement. The Participant agrees
to comply with all rules the Company may establish with respect to the Plan. The Participant
further acknowledges and agrees that this Agreement (and the Plan) constitutes the entire agreement
between the parties with respect to the

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Award and that this Agreement (and the Plan) supersedes any and all prior agreements, whether
written or oral, between the parties with respect to the Award.

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