Document:

exv10w6

Exhibit 10.6

EMPLOYMENT AGREEMENT

     AGREEMENT (the “Agreement”), dated as of the 25th day of February 2011, between
Aspen Insurance U.S. Services Inc., a Delaware corporation, (the “Company”), and Mario Vitale, a
resident of [Address intentionally omitted] (the “Executive”).

     WHEREAS, the Executive and the Company wish to enter into a written agreement setting forth
the terms and conditions of the Executive’s employment with the Company;

     NOW, THEREFORE, in consideration of the premises and the mutual covenants contained herein,
the Company and the Executive hereby agree as follows:

1. Term.

     (a) The Company shall employ the Executive, and the Executive shall serve the Company, on the
terms and subject to the conditions set forth in this Agreement, commencing on a date no later than
the 21st day of March 2011, mutually satisfactory to the Company and the Executive (the
“Effective Date”) and, unless sooner terminated pursuant to paragraph 7, continuing until the date
that is the one year anniversary of the Effective Date (the “Term of Employment”). Absent an
agreement to the contrary between the Company and the Employee, the Effective Date shall be the
21st day of March 2011.

     (b) The Term of Employment shall be extended automatically for one additional year on the last
day before the expiration of the Term of Employment and for one additional year on each anniversary
thereafter until either party gives written notice to the other party of its intention not to
extend this Agreement. Such notice must be given at least 90 days before the then applicable
extension date.

2. Position and Duties.

     (a) Positions, Duties, and Responsibilities. The Executive shall serve as the
President of US Insurance of the Aspen Insurance Group and shall use his best efforts, skill and
abilities to promote the interests of the Company, and to faithfully and diligently perform such
duties and responsibilities as are customarily assigned to that position, and such other duties and
responsibilities as may from time to time be assigned to him by the Co-Chief Executive Officer of
Aspen Insurance (the “Co-CEO”) or by such other member of senior management as shall be designated
by the Co-CEO.

     (b) Time and Attention. Excluding any periods of vacation and sick leave to which the
Executive is entitled, the Executive shall devote substantially all of his attention and

 

 

time during normal working hours to the business and affairs of the Company and its affiliates. It
shall not be considered a violation of the foregoing, however, for the Executive to (i) serve on
boards and committees of a reasonable number of other companies or otherwise participate in,
corporate, industry, educational, religious, civic, or charitable activities or (ii) make and
attend to passive personal investments in such form as will not require any material time or
attention to the operations thereof during normal working time and will not violate the provisions
of paragraph 11 hereof, so long as such activities in clauses (i) and (ii) do not materially
interfere with the performance of the Executive’s responsibilities as an employee of the Company
and to the Company in accordance with this Agreement or violate paragraph 11 of this Agreement.

     (c) Licenses, etc. If requested by the Co-CEO or his designee, the Executive shall
take such industry tests or obtain such industry licenses as shall be necessary or appropriate to
his carrying out the functions contemplated hereby.

3. Compensation. Except as otherwise expressly set forth below, the Executive’s
compensation shall be determined by, and in the sole discretion of, the Co-CEO.

     (a) Annual Base Salary. The Executive shall receive an annual base salary of not less
than seven hundred and fifty thousand dollars ($750,000) during the Term of Employment (the annual
base salary in effect from time to time being referred to as “Annual Base Salary”). The Annual
Base Salary shall be payable in accordance with the Company’s regular payroll practice for senior
officers of the Company, as in effect from time to time. The Annual Base Salary shall be reviewed
from time to time, and, in the sole discretion of the Co-CEO, may be adjusted but may not be
decreased below $750,000 per annum.

     (b) Annual Bonus Plan. The Executive will participate in the Company’s discretionary
bonus arrangements. The Executive’s annual bonus potential will be up to one hundred and twenty
(120%) of current Annual Base Salary. This potential is a target amount and actual bonus payments
will be dependent upon the Company’s overall results each year and the performance of his team’s
results. As a result, the actual bonus paid in any year may be may more or less than this potential
amount. All bonuses are discretionary and at the approval of the Co-CEO and the Compensation
Committee (the “Compensation Committee”) of Aspen Insurance Holdings Limited (“AIHL”). Bonuses, if
earned, shall be payable at the time such bonuses are normally paid but not later than March
15th of the calendar year following the last day of the calendar year in which the bonus
is earned.

     (c) Bonus Compensation 2012. The Executive shall receive a guaranteed bonus of nine
hundred thousand dollars ($900,000) for the year ended 31 December 2011 which will pay out on March
31, 2012, provided that on that date the Executive’s employment has not been terminated by the
Company for Cause under Clause 7(b)(i). This payment will be in lieu of any discretionary
payment to the Executive under Clause 2(b) for the year ending December 31, 2011.

     (d) Long Term Incentive Plan. The Executive will be eligible to be considered for
participation in the Company’s Long Term Incentive Plan for 2011 and future years to the value of
eight hundred and fifty thousand dollars ($850,000) per annum. The grant any such LTIP awards to
the Executive, however, remains subject to the absolute discretion of the Co-

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CEO and the Compensation Committee and the Executive shall have no guarantee of participation in any future
LTIP awards. In addition, the form of award issued under LTIP programs may vary, but in all cases
will be subject to the rules of the Aspen Insurance Holdings Limited 2003 Share Incentive Plan or
replacement plans.

     (e) Restricted Stock Units. Following the Effective Date the Executive will receive an
award of two million two hundred and seventy-six thousand dollars ($2,276,000) (as at the date of
grant) in Restricted Stock Units (“RSU’s”) issued under the AIHL 2003 Share Incentive Plan (the
“Plan”). Subject to the rules of the Plan, the RSU’s will vest over three years, with a third of
the units vesting on each anniversary of the date of issuance. Vesting of the RSU’s will be time
based, with no performance criteria conditions other than continued employment of the Executive at
the date of vesting, except in the event that the Company terminates the Executive’s employment
without Cause or if the Executive’s appointment is terminated for death or Disability.

     (f) Cash Replacement Award. The Executive shall receive a one-time cash replacement
award of one million dollars ($1,000,000). This payment will be paid in the Executive’s first
paycheck under this agreement PROVIDED THAT if this Agreement is terminated by the Executive on a
date which is less than one year after its commencement (other than a termination under Sections
7(a), 7(b)(i), or 7(c)) the Executive shall repay to the Company the entire amount of this payment
and the Company shall be entitled to set-off such amounts against any other payments due to the
Executive by the Company in accordance with the termination of this Agreement.

     (g) Relocation. The Executive will be entitled to relocation support in accordance
with the Company’s Relocation Policy attached to this Agreement. Specifically, the
Company shall pay for the Executive’s temporary furnished housing expense for a six-month period.
The Company also shall pay for the Executive and his wife to relocate from Zurich, Switzerland to
New York.

     (h) Inclusive Nature of Compensation. The compensation provided for in this Section 3
shall be inclusive of any and all fees and other compensation to which the Executive may at any
time be entitled as an officer or director of the Company or any other subsidiaries of AIHL or any
of the affiliates of the Company.

     (i) Former
Employer Indemnity. In the event that any action or proceeding is
threatened or commenced against Executive by his former employer (the “Former Employer”) relating
to the Executive’s employment with the Company as contemplated by this Agreement, whether before or
after Executive begins employment with the Company, the Company will indemnify Executive and hold
him harmless for any damages, costs, liabilities, judgments, interest and settlement to the fullest
extent permitted by its by-laws and applicable law (the “Damages”), provided, however, that the
Company will not have an obligation to defend and/or indemnify the Executive if the Damages arose
out of Executive’s willful malfeasance (which term shall include any willful breach by the
Executive of any legal, fiduciary or regulatory duty of confidence or other duty of fidelity owed
by the Executive to the Former Employer or a failure by the Executive to act in accordance with a
business strategy agreed by the Company), gross misconduct, gross negligence, fraudulent conduct or
illegal conduct. Such indemnification

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shall include the payment of reasonable and actual attorneys’ fees incurred on counsel selected by the Company to defend any action subject to this
indemnity.

4. Employee Benefits; Fringe Benefits. During the Term of Employment,

     (a) to the extent not duplicative of the specific benefits provided herein, the Executive
shall be eligible to participate in all incentive compensation, retirement, and deferred
compensation plans, policies and arrangements that are provided generally to other senior officers
of the Company at a level (in terms of the amount and types of benefits and incentive compensation
that the Executive has the opportunity to receive and the terms thereof) determined in the sole
discretion of the Co-CEO. Specifically in this regard the Executive
will initially be
eligible for 401k funding by the Company of 4% of salary matching contributions (the “Salary
Matching Contribution”) and 6% of salary profit share contributions (the “Profit Share
Contribution”), each subject to the relevant salary limits applicable to the Company’s 401k plan
(the “Salary Cap”). The current Salary Cap applicable to each of the Salary Matching Contribution
and the Profit Share Contribution is two hundred and forty five thousand dollars ($245,000).
Further, subject to approval by AIHL’s Compensation Committee on 27 April 2011, the Company will
put in place arrangements to ensure that the Executive is eligible for total retirement funding
through the Company’s 401k plan and other arrangements equal to (i) 4% of Salary Matching
Contribution subject to the Salary Cap, and (ii) a total of 6% of the Executives Annual Base Salary
in additional contributions (including the Profit Share Contribution) without any salary cap.

     (b) the Executive and, as applicable, the Executive’s covered dependents shall be eligible to
participate in all of the Company’s health and welfare benefit plans (within the meaning of Section
3(1) of the Employee Retirement Income Security Act of 1974, as amended);

     (c) the Executive shall be entitled to receive fringe benefits and to participate in all
employee benefit plans provided for senior executives of the Company (which will include
supplemental life insurance and supplemental long term disability which are comparable to the
parallel benefits which the Executive informed the Company he has from his current Company, namely,
supplemental life insurance in the amount of 2 times Annual Base Salary, and long-term disability
in the amount of 60% of Annual Base Salary), and shall be entitled to avail himself of paid
holidays, as determined from time to time by the Company; and

     (d) the Executive shall be entitled to not less than twenty-four (24) days of Paid Time Off
per calendar year subject to the Company’s applicable vacation policy.

5. Insurance on Executive. The Executive hereby grants the Company the right to obtain
insurance on the Executive’s life for the benefit of the Company in such amount as the Company
shall deem necessary. The Executive agrees to execute all necessary documents and to submit to a
physical in connection therewith. The cost or expense of such insurance shall not be charged to
the Executive.

6. Expenses. The Executive shall be reimbursed by the Company for reasonable and necessary
business expenses actually incurred in rendering the services provided for hereunder, payable in
accordance with customary Company practice, after the Executive presents written

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expense statements or such other supporting information as the Company may customarily require of its executives for
reimbursement of such expenses. Any expense reimbursements shall be made promptly, but in any
event on or before December 31 of the calendar year following the calendar year in which the
Executive incurs the related expense. Any reimbursement in one calendar year shall not affect the
amount that may be reimbursed in any other calendar year and a reimbursement (or right thereto) may
not be exchanged or liquidated for another benefit or payment.

7. Termination of Employment.

     (a) Death or Disability. The Term of Employment shall terminate upon the Executive’s
death. The Company shall be entitled to terminate the Executive’s employment and, accordingly, the
Term of Employment, because of the Executive’s Disability. For purposes of this Agreement, the
Executive shall be deemed to have a Disability if the Executive is entitled to long-term disability
benefits under the Company’s long-term disability plan or policy, as the case may be, as in effect
on the Date of Termination (as that term is defined in subparagraph 7(c)(ii) below) or if no plan
or policy is maintained and the Executive is unable to perform his duty hereunder for 180
consecutive days.

     (b) By the Company.

          (i) The Company may terminate the Executive’s employment and the Term of Employment, without
Cause by delivering to the Executive written Notice of Termination (as that term is defined in
subparagraph 7(d)(i) below), or for Cause by delivering to the Executive a written Notice of
Termination.

          (ii) For purposes of this Agreement, “Cause” means: (A) the Executive’s willful misconduct
that is materially injurious to the Company or any of its affiliates; (B) the Executive’s
intentional failure to act subject to and in accordance with any proper and lawful specific
material direction of the Co-CEO or his designee or the Board of Directors of the Company which
breach is not promptly cured by the Executive after written notice of such breach; (C) the
Executive’s having been convicted of, or entered a plea of nolo contendere to, a crime that
constitutes a felony under the laws of the United States or any State; (D) the Executive’s
violation of any applicable federal or state law governing the Company’s business or of any
applicable rules or regulations promulgated by any regulatory body, the violation of which shall
either disqualify the Executive from employment or association with the Company as an executive or
have a material adverse effect on the Company’s business; provided, however, that any such
violation shall not constitute “cause” if it results from action taken by the Executive in
accordance with instructions from the Co-CEO or his designee or the Board of Directors of the
Company or upon the advice of internal or outside counsel to the Company; or (E) the intentional
breach by the Executive of any written covenant or agreement with the Company or any of their
affiliates not to disclose any information pertaining to the Company or any of its affiliates or
not to compete or otherwise interfere with the Company or any of its affiliates.

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     (c) By Executive for Good Reason.

          (i) The Executive may terminate the Executive’s employment and the Term of Employment for Good
Reason by delivering to the Company written Notice of Termination if the Company does not
substantially cure the grounds stated in such notice within 60 days of its receipt thereof.

          (ii) For purposes of this Agreement, “Good Reason” means the occurrence of any of the
following without the written consent of the Executive, unless the Company cures any such
occurrence after the requisite notice: (i) a material diminution in the Executive’s
responsibilities, duties, authority or title provided for in this Employment Agreement at the
Effective Date; (ii) a material reduction in Executive’s Annual Base Salary; or (iii) a material
breach by either the Company of any of their respective other obligations contained in this
Employment Agreement. Any occurrence of Good Reason shall be deemed waived by the Executive unless
the Executive provides written notice of the event giving rise to Good Reason within ninety (90)
days of the initial existence of such event.

     (d) By Consolidation or Reorganization; Change in Control.

          (i) If the employment of the Executive hereunder shall be terminated solely by reason of the
liquidation of any affiliate for the purposes of consolidation or reorganization or as part of any
arrangement for the consolidation of the undertaking of such affiliate not involving liquidation
(in each case, other than a “Change in Control”, as defined below) and the Executive shall be
offered employment with the consolidated or reorganized company on the same terms as the terms of
this Agreement, the Executive shall have no claim against the Company or any affiliate in respect
of the termination of his employment by the Company.

          (ii) If the employment of the Executive hereunder shall be terminated by the Company without
Cause or by the Executive with Good Reason within the six-month period prior to a Change in Control
or within the two-year period after a Change in Control, in addition to the benefits provided in
Section 8(a), the Executive shall be entitled to the additional following benefits: other than
share options and other equity-based awards granted prior to the date of this Agreement, which
shall vest and be exercisable in accordance with the terms of their grant agreements, all share
options and other equity-based awards shall immediately vest and remain exercisable for the
remainder of their terms;

For purposes of this Agreement, “Change in Control” shall have the same meaning as under the Aspen
Insurance Holdings 2003 Share Incentive Plan as in effect as of the date hereof.

     (e) Termination Procedures.

          (i) Notice of Termination. Any purported termination of the Executive’s employment
(other than by reason of death) shall be communicated by written Notice of Termination from one
party hereto to the other party hereto in accordance with the notice provisions contained in
subparagraph 14(b) hereof. For purposes of this Agreement, a “Notice of Termination” shall mean a
notice that indicates the specific termination provision in

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this Agreement relied upon and sets forth in reasonable detail the facts and circumstances claimed to provide a basis for termination
of employment under the provision so indicated.

          (ii) Date of Termination. For purposes of this Agreement, “Date of Termination” shall
mean the date specified in the Notice of Termination or the date of the Executive’s death so long
as such date constitutes a “separation from service” as that term is defined in Section 409A of the
Internal Revenue Code of 1986, as amended, and any related regulations promulgated thereunder
(“Section 409A”); provided, however, that the date of termination in case of a termination by the
Executive for Good Reason may not be earlier than 90 days after the receipt of the Notice of
Termination by the Company.

          (iii) No Waiver. The failure to set forth any fact or circumstance in a Notice of
Termination shall not constitute a waiver of the right to assert such fact or circumstance in an
attempt to enforce any right under or provision of this Agreement.

8. Obligations of the Company upon Termination.

     (a) Post-Employment Benefits. If the Executive’s employment is terminated by the
Company for any reason other than Cause, death or Disability or by the Executive for Good Reason
after the requisite notice and failure of the Company to cure the written grounds underlying the
“Good Reason”,

          (i) the Company shall pay or provide to the Executive in cash, no later than twenty (20)
business days after the normal payment date for each, (a) any portion of the Executive’s earned but
unpaid Annual Base Salary to the date of termination, (b) any earned but unpaid prior year Annual
Bonus; (c) any other earned but unpaid equity and/or incentive awards, (d) a payment reflecting
accrued but unused vacation days (subject to the limitation in subparagraph 4(d)), and (e) any
unreimbursed business expenses subject to paragraph 6 (collectively the “Accrued Obligations”);

          (ii) subject to compliance by the Executive with the provisions of paragraph 8, the Company
shall pay to the Executive within twenty (60) business days a lump sum equal to one hundred percent
(100%) the Executive’s then Annual Base Salary;

          (iii) subject to compliance by the Executive with the provisions of paragraph 8, the Company
shall pay to the Executive within twenty (60) business days a lump sum equal to the lesser of (i)
the Executive’s then current annual bonus potential as determined in accordance with clause 3(b),
or (ii) the average actual annual bonus paid to the Executive for the three (3) years preceding the
year in which the Date of Termination occurs (including for these purposes the payment made under
paragraph 3(c) above); and

          (iv) the RSU’s granted in clause 3(e) in the amount of $2,276,000 shall, to the extent they
have not already done so, continue to vest and become exercisable on each anniversary.

     (b) Termination by the Company for Cause or the Executive Without Good Reason. If the
Executive’s employment is terminated by the Company for Cause or by the Executive without Good
Reason, the Company shall pay to the Executive in cash within twenty

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(20) business days after the normal payment date for each the following amounts the Accrued Obligations as defined in clause
8(a)(i) above.

     (c) Termination due to death or Disability. If the Executive’s employment is
terminated due to death or Disability, the Company shall pay to the Executive (or to the
Executive’s estate or personal representative, in the case of the Executive’s death) in cash (i) on
the normal payment date for each Accrued Obligation (as defined in clause 8(a)(i) above) and (ii)
on the normal payment date for a prorated annual bonus based on the actual annual bonus earned for
the year in which the Date of Termination occurs, prorated based on the fraction of the year the
Executive was employed. In addition, the RSU’s granted in clause 3(e) in the amount of $2,276,000
shall immediately vest, to the extent they have not already done so, and shall be immediately
distributed to the Executive (or, in the case of death, to the Executive’s estate). After making
such payment(s), the Company shall have no further obligations under this Agreement.

     (d) Six-Month Delay. Notwithstanding any provision herein to the contrary, if the
Executive is a “specified employee” within the meaning of Section 409A on the Date of Termination
and the right to any payment as a result of the Executive’s separation from service provides for
the “deferral of compensation” within the meaning of Section 409A, then all such payments (other
than payments qualifying as a short-term deferral under Treasury Regulation § 1.409A-1(b)(4), or
treated as not providing for a deferral of compensation under the separation pay provisions of
Treasury Regulation § 1.409A-1(b)(9)(iii) or § 1.409A-1(b)(9)(v)) shall not be made or commence
during the period beginning on the Date of Termination and ending on the date that is six months
following the Date of Termination or, if earlier, on the date of the Executive’s death, if the
earlier making of such payment would result in tax penalties being imposed on the Executive under
Section 409A. The amount of any payment that would otherwise be paid to the Executive during this
period shall instead be paid to the Executive on the first business day following the date that is
six months following the Date of Termination or, if earlier, the date of the Executive’s death.

9. Release. Notwithstanding any provision herein to the contrary, the Company will require
that, prior to payment of any amount or provision of any benefit under paragraph 8 of this
Agreement (other than an Accrued Obligation or due to the Executive’s death), the Executive shall
within sixty (60) days following the Date of Termination have executed with all periods of
revocation expired a complete release of the Company and their affiliates and related parties in
such form as is reasonably required by the Company.

10. Non-Exclusivity of Rights. Except as otherwise provided in this Agreement, nothing in
this Agreement shall prevent or limit the Executive’s continuing or future participation in any
plan, program, policy or practice provided by the Company or any of its affiliated companies for
which the Executive may qualify (other than severance policies). Vested benefits and other amounts
that the Executive is otherwise entitled to receive under any other plan, program, policy, or
practice of, or any contract or agreement with, the Company or any of its affiliated companies on
or after the Date of Termination shall be payable in accordance with the terms of each such plan,
program, policy, practice, contract, or agreement, as the case may be, except as expressly modified
by this Agreement.

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11. Non-Competition; Confidential Information; and Non-Solicitation.

     (a) Non-Competition. During the Term of Employment and for a period of one year
following the termination of the Executive’s employment if he is entitled to severance payments
pursuant to subparagraph 8(a), the Executive shall not, without the prior written consent of the
Company, as a shareholder, officer, director, partner, consultant, employee or otherwise, engage in
any business or enterprise which is “in competition” with the Company, its affiliates, or their
successors or assigns (such entities collectively referred to hereinafter in this paragraph 11 as
the “Company”); provided, however, that the Executive’s ownership of less than five percent of the
issued and outstanding voting securities of a publicly traded company shall not, in and of itself,
be deemed to constitute such competition. A business or enterprise is deemed to be “in
competition” if it is engaged, in any of the geographical regions in which the Company conducts the
casualty reinsurance underwriting business on the Date of Termination or any other business which
the Executive is supervising.

     (b) Confidential Information. The Executive shall hold in a fiduciary capacity for
the benefit of the Company all secret or confidential information, knowledge, trade secrets,
methods, know-how or data relating to the Company and their businesses or acquisition prospects
(including the compensation and other terms of employment of their employees) that the Executive
obtained or obtains during the Executive’s employment by the Company and that is not and does not
become generally known to the public (other than as a result of the Executive’s violation of this
paragraph 11) (“Confidential Information”). Except as may be required and appropriate in
connection with carrying out his duties under this Agreement, the Executive shall not communicate,
divulge, or disseminate any material Confidential Information at any time during or after the
Executive’s employment with the Company, except with the prior written consent of the Company or as
otherwise required by law or legal process; provided, however, that if so required, the Executive
will provide the Company with reasonable notice to contest such disclosure.

     (c) Non-Solicitation of Employees. The Executive recognizes that he may possess
confidential information about other employees of the Company relating to their education,
experience, skills, abilities, compensation and benefits, and inter-personal relationships with
suppliers to and customers of the Company. The Executive recognizes that the information he will
possess about these other employees may not be generally known, may be of substantial value to the
Company in developing its respective businesses and in securing and retaining customers, and may be
acquired by him because of his business position with the Company. The Executive agrees that, for
a period of one year following the termination of the Executive’s employment if he is entitled to
severance payments pursuant to subparagraph 8(a), he will not, directly or indirectly, initiate any
action to solicit or recruit or hire anyone who is then an employee of the Company for the purpose
of being employed by him or by any business, individual, partnership, firm, corporation or other
entity on whose behalf he is acting as an agent, representative or employee and that he will not
convey any such confidential information or trade secrets about other employees of the Company to
any other person except within the scope of the Executive’s duties hereunder.

     (d) Non-Interference with Customers. The Executive agrees that, for a period of one
year following the termination of the Executive’s employment if he is entitled to

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 severance
payments pursuant to subparagraph 8(a), he will not interfere with any business relationship
between the Company and any of its customers.

     (e) Remedies; Severability.

          (i) The Executive acknowledges that his skills and position in the insurance industry are
unique and if the Executive shall breach or threaten to breach any provision of subparagraphs 11(a)
through (d), the damages to the Company may be substantial, although difficult to ascertain, and
money damages will not afford the Company an adequate remedy. Therefore, if the provisions of
subparagraphs 11(a) through (d) are violated, in whole or in part, the Company shall be entitled to
specific performance and injunctive relief (without having to post any bond), without prejudice to
other remedies the Company may have at law or in equity.

          (ii) If any term or provision of this paragraph 11, or the application thereof to any person
or circumstances shall, to any extent, be invalid or unenforceable, the remainder of this paragraph
11, or the application of such term or provision to persons or circumstances other than those as to
which it is held invalid or unenforceable, shall not be affected thereby, and each term and
provision of this paragraph 11 shall be valid and enforceable to the fullest extent permitted by
law. Moreover, if a court of competent jurisdiction deems any provision hereof to be too broad in
time, scope, or area, it is expressly agreed that such provision shall be reformed to the maximum
degree that would not render it unenforceable.

12. Assignment. This is a personal services agreement and the Executive may not assign
this Agreement to any third party. The Company may assign this Agreement and the benefits
hereunder without the consent of the Executive, without being relieved of any liability hereunder,
to one of its direct or indirect “affiliates” or “associates” as those terms are defined in Rule
405 of the Rules and Regulations promulgated under the Securities Act of 1933. The Company may
assign this Agreement and the benefits hereunder to any entity (corporate or other) into which the
Company or the business of the Company may be merged, consolidated or transferred but nothing
contained herein shall release the Company of any of its obligations hereunder.

13. Arbitration. Except for matters covered under paragraph 11, in the event of any
dispute or difference between the Company and the Executive with respect to the subject matter of
this Agreement and the enforcement of rights hereunder, either the Executive or the Company may, by
written notice to the other, require such dispute or difference to be submitted to arbitration.
The arbitrator or arbitrators shall be selected by agreement of the parties or, if they cannot
agree on an arbitrator or arbitrators within 30 days after the date arbitration is required by
either party, then the arbitrator or arbitrators shall be selected by the American Arbitration
Association (the “AAA”) upon the application of the Executive or the Company. The determination
reached in such arbitration shall be final and binding on both parties without any right of appeal
or further dispute. Execution of the determination by such arbitrator may be sought in any court
of competent jurisdiction. The arbitrators shall not be bound by judicial formalities and may
abstain from following the strict rules of evidence and shall interpret this Agreement as an
honorable engagement and not merely as a legal obligation. Unless otherwise agreed by the parties,
any such arbitration shall take place in Stamford, Connecticut.

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14. Miscellaneous.

     (a) Governing Law and Captions. This Agreement shall be governed by, and construed in
accordance with, the laws of New York without reference to principles of conflict of laws. The
captions of this Agreement are not part of the provisions hereof and shall have no force or effect.

     (b) Notices. All notices and other communications under this Agreement shall be in
writing and shall be given by hand delivery or by facsimile (provided confirmation of receipt of
such facsimile is received) to the other party or by registered or certified mail, return receipt
requested, postage prepaid, or by Federal Express or other nationally-recognized overnight courier
that requires signatures of recipients upon delivery and provides tracking services, addressed as
follows:

If to the Executive:

Mario Vitale

[Address intentionally omitted]

If to the Company:

John Cavoores

Co-Chief Executive Officer

Aspen Insurance US Services, Inc

600 Atlantic Ave., Ste 2100

Boston, MA. 02210

or to such other address as either party furnishes to the other in writing in accordance with this
subparagraph 14(b). Notices and communications shall be effective when actually received by the
addressee.

     (c) Amendment. This Agreement may not be amended or modified except by a written
agreement executed by the parties hereto.

     (d) Severability. The invalidity or unenforceability of any provision of this
Agreement shall not affect the validity or enforceability of any other provision of this Agreement.
If any provision of this Agreement shall be held invalid or unenforceable in part, the remaining
portion of such provision, together with all other provisions of this Agreement, shall remain valid
and enforceable and continue in full force and effect to the fullest extent consistent with law.

     (e) Withholding. Notwithstanding any other provision of this Agreement, the Company
may withhold from amounts payable under this Agreement all federal, state, local, and foreign taxes
that are required to be withheld by applicable laws or regulations. All cash

11

 

amounts required to be paid hereunder shall be paid in United States dollars. Except as otherwise specifically
provided herein, the Executive shall be responsible for all federal, state and local taxes on all
compensation and benefits provided hereunder.

     (f) Waiver. The Executive’s or the Company’s failure to insist upon strict compliance
with any provision of, or to assert any right under, this Agreement shall not be deemed to be a
waiver of such provision or right or of any other provision of or right under this Agreement.

     (g) Entire Understanding. The Executive and the Company acknowledge that this
Agreement supersedes and terminates any other severance and employment agreements between the
Executive and the Company or any Company affiliates. This Agreement may be executed in several
counterparts, each of which shall be deemed an original, and said counterparts shall constitute but
one and the same instrument.

     (h) Rights and Benefits Unsecured. The rights and benefits of the Executive under
this Agreement may not be anticipated, assigned, alienated, or subject to attachment, garnishment,
levy, execution, or other legal or equitable process except as required by law. Any attempts by
the Executive to anticipate, alienate, assign, sell, transfer, pledge or encumber the same shall be
void. Payments hereunder shall not be considered assets of the Executive in the event of
insolvency or bankruptcy.

     (i) Noncontravention. The Company represents that the Company is not prevented from
entering into, or performing this Agreement by the terms of any law, order, rule or regulation, its
by-laws or declaration of trust, or any agreement to which it is a party, other than which would
not have a material adverse effect on the Company’s ability to enter into or perform this
Agreement.

     (j) Paragraph and Subparagraph Headings. The paragraph and subparagraph headings in
this Agreement are for convenience of reference only; they form no part of this Agreement and shall
not affect its interpretation.

     (k) Section 409A Compliance. This Agreement is intended to meet the requirements of
Section 409A, and shall be interpreted and construed consistent with that intent.

12

 

     IN WITNESS WHEREOF, the Executive has hereunto set the Executive’s hand and, pursuant to the
authorization of the Board, the Company has caused this Agreement to be executed, all as of the day
and year first above written.

	 	 	 	 	 	 	 	 	 

	ASPEN INSURANCE U.S. SERVICES INC.
	 	 	 	MARIO VITALE	 	 
	 
	 	 	 	 	 	 	 	 
	By:

	 	/s/ Christopher Woodman
	 	 	 	/s/ Mario Vitale	 	 
	 

	 	 
	 	 	 	 
	 	 
	 

	 	Name: Christopher Woodman
	 	 	 	Mario Vitale	 	 
	 

	 	Title: Group Head of Human Resources	 	 	 	 	 	 

Countersigned, but not in an employing capacity by:

ASPEN INSURANCE HOLDINGS LIMITED

	 	 	 	 	 
	 	 
	By:  	/s/ Michael Cain
 	 
	 	Name:  	Michael Cain 	 
	 	Title:  	Group General Counsel 	 
	 

13exv10w39

Exhibit 10.39

Execution Version

ASPEN INSURANCE HOLDINGS LIMITED

PERFORMANCE SHARE AWARD AGREEMENT

          THIS AGREEMENT (the “Agreement”), is made effective as of the 9th day of February,
2011 (hereinafter called the “Date of Grant”), between Aspen Insurance Holdings Limited, a Bermuda
corporation (hereinafter called the “Company”), and «Full_Name» (hereinafter called the
“Participant”):

R E C I T A L S:

          WHEREAS, the Company has adopted the Aspen Insurance Holdings 2003 Share Incentive Plan, as
amended from time to time (the “Plan”), which Plan is incorporated herein by reference and made a
part of this Agreement. Capitalized terms not otherwise defined herein shall have the same
meanings as in the Plan; and

          WHEREAS, the Committee has determined that it would be in the best interests of the Company
and its shareholders to grant the performance shares provided for herein to the Participant
pursuant to the Plan and the terms set forth herein.

          NOW THEREFORE, in consideration of the mutual covenants hereinafter set forth, the parties
agree as follows:

	1.	 	Grant of Performance Shares. The Company hereby awards to the Participant 7,328
Shares, payment of which is dependent upon the performance of the Company as described in
Section 2 of this Agreement (the “Performance Shares”).
	 
	2.	 	Vesting. The Performance Shares shall vest and become payable only to the extent
that the Return on Equity (calculated as described in Section 2(a) below, the “ROE”) and the
service requirements described below are achieved.

	 	(a)	 	For purposes of this Agreement, “ROE” shall be equal to net income determined
under United States Generally Accepted Accounting Principles (“US GAAP”) after
deduction of the cost of all Awards granted under the Plan as a percentage of weighted
average shareholders’ equity, which shall be determined by the Board based on the
Company’s audited financials under US GAAP.
	 
	 	(b)	 	For purposes of this Agreement, “2011 ROE” shall be equal to the Company’s
actual ROE for the fiscal year ended December 31, 2011 (the “2011 Fiscal Year”).
	 
	 	(c)	 	For purposes of this Agreement, “2012 ROE” shall be equal to the Company’s actual
ROE for the fiscal year ended December 31, 2012 (the “2012 Fiscal Year”).
	 
	 	(d)	 	For purposes of this Agreement, “2013 ROE” shall be equal to the Company’s
actual ROE for the fiscal year ended December 31, 2013 (the “2013 Fiscal Year”).

 

 

	 	(e)	 	Subject to the Participant’s continued Employment with the Company (which
Employment shall not include the performance of services under a notice of termination
or resignation), a maximum of one-third (1/3) of the Performance Shares awarded
hereunder (the “2011 ROE Award”) shall be eligible for vesting (“Eligible Shares”) upon
the later of (i) the date the Company’s outside auditors complete the audit of the
Company’s financial statements containing the information necessary to compute the
Company’s ROE for the 2011 Fiscal Year or (ii) the date such ROE is approved by the
Board of Directors or an authorized committee thereof, but only to the extent provided
below:

	 	 	 	 	 
	2011 ROE	 	Percentage of Eligible Shares	 
	< 6%	 	 	0%	 
	6%	 	 	10%	 
	11%	 	 	100%	 
	≥ 21%	 	 	200%	 

Interim percentages to be pro-rated.

	 	 	 	Notwithstanding the foregoing, if the Company’s actual ROE for the 2011 Fiscal Year
is (i) less than 6%, then none of the Performance Shares subject to the 2011 ROE
Award shall be Eligible Shares, (ii) greater than 11% and the average ROE over the
2011 Fiscal Year and the immediately preceding fiscal year is less than 6%, then the
Percentage of Eligible Shares shall be 100%; or (iii) greater than 11% and the
average ROE over the 2011 Fiscal Year and the immediately preceding fiscal year is
6% or greater, then the Percentage of Eligible Shares shall be in accordance with
the table above.
	 
	 	(f)	 	Subject to the Participant’s continued Employment with the Company (which
Employment shall not include the performance of services under a notice of termination
or resignation), a maximum of one-third (1/3) of the Performance Shares awarded
hereunder (the “2012 ROE Award”) shall become Eligible Shares upon the later of (i) the
date the Company’s outside auditors complete the audit of the Company’s financial
statements containing the information necessary to compute the Company’s ROE for the
2012 Fiscal Year or (ii) the date such ROE is approved by the Board of Directors or an
authorized committee thereof, but only to the extent provided in a schedule to be
provided to the Participant during the first quarter of the 2012 Fiscal Year.
	 
	 	 	 	Notwithstanding the schedule to be provided to the Participant during the first
quarter of the 2012 Fiscal Year, if the Company’s actual ROE for the 2012 Fiscal
Year is (i) less than the minimum vesting threshold determined in accordance with
the schedule provided, then none of the Performance Shares subject to the 2012 ROE
Award shall be Eligible Shares, (ii) greater than the target vesting level at 100%
vesting determined in accordance with the schedule provided and the average ROE over
the 2012 Fiscal Year and the 2011 Fiscal Year is less than the average of the
minimum vesting thresholds for such years, then the Percentage of Eligible Shares
shall be 100%; or (iii) greater than the target vesting level at 100%

 

 

	 	 	 	vesting determined in accordance with the schedule provided and the average ROE over
the 2012 Fiscal Year and the 2011 Fiscal Year is equal to or greater than the
average of the minimum vesting thresholds for such years, then the Percentage of
Eligible Shares shall be in accordance with the table provided to the Participant.
	 
	 	(g)	 	Subject to the Participant’s continued Employment with the Company (which
Employment shall not include the performance of services under a notice of termination
or resignation), a maximum of one-third (1/3) of the Performance Shares awarded
hereunder (the “2013 ROE Award”) shall become Eligible Shares upon the later of (i) the
date the Company’s outside auditors complete the audit of the Company’s financial
statements containing the information necessary to compute the Company’s ROE for the
2013 Fiscal Year or (ii) the date such ROE is approved by the Board of Directors or an
authorized committee thereof, but only to the extent provided in a schedule to be
provided to the Participant during the first quarter of the 2013 Fiscal Year.
	 
	 	 	 	Notwithstanding the schedule to be provided to the Participant during the first
quarter of the 2013 Fiscal Year, if the Company’s actual ROE for the 2013 Fiscal
Year is (i) less than the minimum vesting threshold determined in accordance with
the schedule provided, then none of the Performance Shares subject to the 2013 ROE
Award shall be Eligible Shares, (ii) greater than the target vesting level at 100%
vesting determined in accordance with the schedule provided and the average ROE over
the 2013 Fiscal Year and the 2012 Fiscal Year is less than the average of the
minimum vesting thresholds for such years, then the Percentage of Eligible Shares
shall be 100%; or (iii) greater than the target vesting level at 100% vesting
determined in accordance with the schedule provided and the average ROE over the
2013 Fiscal Year and the 2012 Fiscal Year is equal to or greater than the average of
the minimum vesting thresholds for such years, then the Percentage of Eligible
Shares shall be in accordance with the table provided to the Participant.
	 
	 	(h)	 	Subject to the Participant’s continued Employment with the Company (which
Employment shall not include the performance of services under a notice of termination
or resignation), all Eligible Shares shall become vested upon the later of (i) the date
the Company’s outside auditors complete the audit of the Company’s financial statements
containing the information necessary to compute the Company’s ROE for the 2013 Fiscal
Year or (ii) the date such ROE is approved by the Board of Directors or an authorized
committee thereof.
	 
	 	(i)	 	In connection with any event described in Section 10(a) of the Plan or in the
event of a change in applicable accounting rules, the Committee shall make such
adjustments in the terms of the Performance Shares as it shall determine shall be
necessary to equitably reflect such event in order to prevent dilution or enlargement
of the potential benefits of the Performance Shares. The Committee’s determination as
to any such adjustment shall be final.
	 
	 	(j)	 	If the Participant’s Employment with the Company is terminated for any reason,
the Performance Shares shall, to the extent not then vested, be canceled by the Company
without consideration.

 

 

	 	(k)	 	Any Performance Shares that do not become Eligible Shares by reason of the
Company’s failure to achieve an ROE as set forth above (or, if applicable, as set forth
in schedules to be provided to the Participant) shall immediately be forfeited without
consideration.
	 
	 	(l)	 	Notwithstanding anything to the contrary contained herein, in the event that
the Participant’s Employment with the Company is terminated (i) due to the
Participant’s death or (ii) by the Company due to the Participant’s Disability, all
Eligible Shares shall vest in full on the date of such termination of Employment. For
the avoidance of doubt, any Performance Shares that have not become Eligible Shares on
or before the date of such termination of Employment shall be forfeited on such date
without consideration. For purposes of this Agreement, “Disability” shall mean the
inability of a Participant to perform in all material respects his or her duties and
responsibilities to the Company, or any Affiliate of the Company, by reason of a
physical or mental disability or infirmity which inability is reasonably expected to be
permanent and has continued (i) for a period of six consecutive months or (ii) such
shorter period as the Committee may determine in good faith. The Disability
determination shall be in the sole discretion of the Committee and a Participant (or
his or her representative) shall furnish the Committee with medical evidence
documenting the Participant’s disability or infirmity, which is reasonably satisfactory
to the Committee.

	3.	 	Payment.

	 	(a)	 	The Company shall deliver to the Participant one Share for each vested
Performance Share. Any fractional share will be rounded down to the nearest whole
Share and the remainder forfeited.
	 
	 	(b)	 	Except as otherwise provided in the Plan, vested Performance Shares shall be
paid to the Participant as soon as practicable after the date such Performance Shares
become vested, but in no event later than the fifteenth (15th) day of the
third (3rd) month following the end of the fiscal year in which the
Performance Shares become vested.
	 
	 	(c)	 	When Performance Shares are paid, the Company shall issue certificates in the
Participant’s name for such. However, the Company shall not be liable to the
Participant for damages relating to any delays in issuing the certificates to him, any
loss of the certificates, or any mistakes or errors in the issuance of the certificates
or in the certificates themselves.

	4.	 	No Right to Continued Employment. The granting of the Performance Shares evidenced
hereby and this Agreement shall impose no obligation on the Company or any Affiliate to
continue the Employment of the Participant and shall not lessen or affect the Company’s or its
Affiliate’s right to terminate the Employment of such Participant.
	 
	5.	 	Legend on Certificates. The certificates representing the Shares paid in settlement
of Performance Shares shall be subject to such stop transfer orders and other restrictions as
the Committee may deem advisable under the Plan or the rules, regulations, and other
requirements of the U.S. Securities and Exchange Commission, any stock exchange upon which
such Shares are listed, and any applicable laws, and the Committee may cause a legend or
legends to be put on any such certificates to make appropriate reference to such
restrictions.

 

 

	6.	 	Transferability. The Performance Shares may not be assigned, alienated, pledged,
attached, sold or otherwise transferred or encumbered by the Participant otherwise than by
will or by the laws of descent and distribution, and any such purported assignment,
alienation, pledge, attachment, sale, transfer or encumbrance shall be void and unenforceable
against the Company or any Affiliate; provided that the designation of a beneficiary shall not
constitute an assignment, alienation, pledge, attachment, sale, transfer or encumbrance. For
avoidance of doubt, Shares issued to the Participant in payment of vested Performance Shares
pursuant to Section 3 hereof shall not be subject to any of the foregoing transferability
restrictions.
	 
	7.	 	Withholding. The Participant may be required to pay to the Company or any Affiliate
and the Company shall have the right and is hereby authorized to withhold, any applicable
withholding taxes in respect of Performance Shares and to take such other action as may be
necessary in the opinion of the Committee to satisfy all obligations for the payment of such
withholding taxes.
	 
	8.	 	Securities Laws. Upon the acquisition of any Shares pursuant to settlement of
Performance Shares, the Participant will make or enter into such written representations,
warranties and agreements as the Committee may reasonably request in order to comply with
applicable securities laws or with this Agreement.
	 
	9.	 	Bermuda Government Regulations. No Shares shall be issued pursuant to this Agreement
unless and until all relevant licenses, permissions and authorizations required to be granted
by the Government of Bermuda, or by any authority or agency thereof, shall have been duly
received.
	 
	10.	 	Notices. Any notice necessary under this Agreement shall be addressed to the Company
in care of its Secretary at the principal executive office of the Company and to the
Participant at the address appearing in the personnel records of the Company for the
Participant or to either party at such other address as either party hereto may hereafter
designate in writing to the other. Any such notice shall be deemed effective upon receipt
thereof by the addressee.
	 
	11.	 	Choice of Law. THIS AGREEMENT SHALL BE GOVERNED BY AND CONSTRUED IN ACCORDANCE WITH
THE LAWS OF BERMUDA, without regard to conflicts of laws principles.
	 
	12.	 	Performance Shares Subject to the Plan. By entering into this Agreement the
Participant agrees and acknowledges that the Participant has received and read a copy of the
Plan. The Performance Shares are subject to the Plan (including without limitation the
arbitration provision), and the terms and provisions of the Plan, as it may be amended from
time to time, are hereby incorporated herein by reference. In the event of a conflict between
any term or provision contained herein and a term or provision of the Plan, the applicable
terms and provisions of the Plan will govern and prevail.
	 
	13.	 	Rights as a Shareholder. The Participant shall have no rights as a shareholder, and
shall not receive dividends, with respect to any Performance Shares until the Performance
Shares have been paid out and Share certificates have been issued to the Participant.

 

 

	14.	 	Fiscal Year. If the Company’s fiscal year is changed to other than a calendar year,
the references to calendar year in this Agreement shall be adjusted to appropriately reflect
the change.
	 
	15.	 	Signature in Counterparts. This Agreement may be signed in counterparts, each of
which shall be an original, with the same effect as if the signatures thereto and hereto were
upon the same instrument.

          IN WITNESS WHEREOF, the parties hereto have executed this Agreement.

	 	 	 	 	 
	 	ASPEN INSURANCE HOLDINGS LIMITED

 	 
	 	By:  	
 	 

	 	 	 	 	 
	AGREED AND ACKNOWLEDGED AS

OF THE DATE FIRST ABOVE WRITTEN:

 	 	 
	 	 	 
	Participant

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