Exhibit 10.1

MANAGEMENT CONSULTING AGREEMENT
MANAGEMENT CONSULTING AGREEMENT, dated March 28, 2019 (this “Agreement”), by and
between ASPEN INSURANCE HOLDINGS LIMITED, a Bermuda exempted company (the
“Company”), and APOLLO MANAGEMENT HOLDINGS, L.P., a Delaware limited partnership
(the “Service Provider”).

RECITALS
WHEREAS, the Service Provider has expertise in the areas of finance, strategy,
investment, acquisitions and other matters relating to the Company, its direct
and indirect divisions and subsidiaries, and, where applicable, parent entities
and controlled affiliates (collectively, the “Company Group”) and their
businesses;
WHEREAS, the Company desires to avail itself of the Service Provider’s expertise
and consequently has requested that the Service Provider make such expertise
available from time to time to render certain management consulting and advisory
services related to the business and affairs of the Company Group and the review
and analysis of certain financial and other transactions; and
WHEREAS, the Service Provider and the Company agree that it is in their
respective best interests to enter into this Agreement whereby, for the
consideration specified herein, the Service Provider shall provide the services
identified herein to the Company Group on the terms and subject to the
conditions set forth herein.
NOW, THEREFORE, in consideration of the foregoing, and the mutual agreements and
covenants set forth herein and other good and valuable consideration, the
receipt and adequacy of which are hereby acknowledged, the parties hereto agree
as follows:
Section 1.
Retention of the Service Provider.

The Company retains the Service Provider to provide the services hereunder, and
the Service Provider accepts such retention, upon the terms and subject to the
conditions set forth in this Agreement.
Section 2.
Term.

(a)    This Agreement shall commence on, and shall be effective from, the
Commencement Date, and shall terminate upon the earliest to occur of (i) the
Termination Date (as defined below), (ii) a Termination Event (as defined below)
and (iii) the written agreement by each of the Service Provider and the Company
to such effect.
(b)    “Termination Date” means the date that is the eight (8) year anniversary
of the Commencement Date; provided, that, on each of the eight (8) year and nine
(9) year anniversaries of the Commencement Date, the Termination Date shall be
automatically extended

    

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by one successive twelve (12) month period absent contrary notice by either
party given not less than thirty (30) days prior to such anniversary date. For
the avoidance of doubt, in no event shall the Termination Date occur later than
the ten (10) year anniversary of the Commencement Date.
(c)    “Termination Event” means the consummation of any transaction or series
of transactions (including any merger, consolidation, disposition,
recapitalization or issuance or sale of assets or equity interests, whether
pursuant to one or more Underwritten Offerings (as defined below), private sales
or otherwise), whether or not related, as a result of which New Holders (as
defined below) become the beneficial owner, directly or indirectly, of more than
ninety percent (90%) of the ordinary shares or other common equity and voting
securities of the Company Group. “New Holders” means one or more Persons that
are not Initial Holders; “Initial Holders” means (A) holders of equity interests
of Highlands Holdings, Ltd. (“Parent Holdings”) as of the Commencement Date, (B)
any Persons who acquire equity interests of Parent Holdings during the six (6)
month period following the Commencement Date, (C) any directors, officers,
employees and/or other members of management of Parent Holdings and/or its
subsidiaries who acquire or receive equity interests of Parent Holdings at any
time in their capacities as such and/or (D) any Affiliates (as defined below) of
any of the foregoing Persons described in clauses (A) or (B) of this definition.
(d)    “Commencement Date” means February 15, 2019, which is the Closing Date,
as defined in the Agreement and Plan of Merger, dated as of August 27, 2018 (the
“Transaction Agreement”), by and among the Company, Highlands Holdings, Ltd. and
Highlands Merger Sub, Ltd.
(e)    Notwithstanding the foregoing, the (i) obligations of the Company Group
pursuant to Sections 3(d), 3(e), 3(f), 4(c), 4(d), 4(f) and 4(g) and (ii)
provisions of Section 5 through Section 14 shall survive any termination of this
Agreement.
Section 3.
Management Consulting Services.

(a)    The Service Provider shall advise the Company Group concerning such
management matters that relate to proposed financial transactions, acquisitions
and other senior management matters related to the business, administration and
policies of the members of the Company Group (including the analysis of the
return on investment of capital and other expenditures and deployment projects),
in each case as the Company shall reasonably and specifically request by way of
written notice to the Service Provider, which notice shall specify the services
required of the Service Provider and shall include all background materials and
information necessary for the Service Provider to complete such services. If
requested by the Company to provide such services, the Service Provider shall
devote such time to any such written request as the Service Provider shall deem,
in its good faith discretion, necessary. Such consulting services, in the
Service Provider’s good faith discretion, shall be rendered in person or by
telephone or other communication. The Service Provider shall have no obligation
to any member of the Company Group as to the manner and time of rendering its
services hereunder, and no member of the Company Group shall have any right to
dictate or direct the details of the services rendered hereunder.

    
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(b)    The Company shall promptly provide any materials or information that the
Service Provider may reasonably request in connection with the provision of
services by the Service Provider pursuant to the terms and conditions of this
Agreement or to comply with Securities and Exchange Commission or other legal or
regulatory requirements (any such materials or information so furnished, the
“Information”). The Company recognizes and confirms that the Service Provider
(i) shall use and rely primarily on the Information and on information available
from generally recognized public sources in performing the services contemplated
by this Agreement without having independently verified the same, (ii) does not
assume any responsibility or liability whatsoever for the accuracy or
completeness of the Information and such other information and (iii) is entitled
to rely upon the Information without independent verification.
(c)    The Service Provider shall perform all services to be provided hereunder
(i) in support of the members of management and boards of directors (or
equivalent governing body) of the Company Group but (ii) as an independent
contractor to the Company Group and not as an employee, agent, partner of,
member of a joint venture with, equity holder or representative of any member of
the Company Group. The Service Provider shall not have any authority to act for
or to bind any member of the Company Group while acting in its capacity as an
advisor to the Company Group under this Agreement without the Company’s prior
written consent.
(d)    This Agreement shall in no way prohibit the Service Provider, its
Affiliates, or any of its or its Affiliates’ current or former limited partners,
general partners, directors, members, officers, managers, employees, agents,
independent contractors, equity holders, affiliates, advisors or representatives
(collectively, “Representatives”) from engaging in other activities or
performing services for its or their own account or for the account of others,
including for any Person that may be in direct or indirect competition with any
business of any member of the Company Group, and the Company, on behalf of each
member of the Company Group, disclaims to the fullest extent permitted by law
any such prohibition thereon.
(e)    The Service Provider shall not have, by reason of this Agreement, a
fiduciary relationship in respect of the Company Group, and nothing in this
Agreement is intended to or shall be so construed as to impose upon the Service
Provider, its Affiliates or any of the Service Provider’s or its Affiliates’
Representatives, any obligation, except as expressly set forth in this
Agreement.
(f)    Any advice or opinions provided by the Service Provider may not be
referred to publicly or disclosed to any third party (other than the Company’s
or any of its affiliates’ legal, tax, financial or other advisors, each of which
agrees to keep such advice or opinions confidential), except in accordance with
the Service Provider’s prior written consent.
Section 4.
Compensation.

(a)    As consideration for the Service Provider’s agreement to provide the
services set forth in Section 3(a), subject to Section 4(e) and to waiver or
deferral as described in Section 4(g) below, the Company shall pay, or cause to
be paid, to the Service Provider a nonrefundable annual management consulting
fee equal to the greater of (i) one percent (1%) of the consolidated net income
of the Company and its subsidiaries for the applicable fiscal year and

    
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(ii) $5 million (the “Consulting Fee”). Such Consulting Fee shall be payable as
follows: (x) $1.25 million shall be payable on the first business day following
the end of each fiscal quarter of such fiscal year and (y) following the
completion of the Company’s annual audit in respect of such fiscal year, the
remaining unpaid amount of the Consulting Fee, if any (after taking into account
the payments made in accordance with clause (x)), shall be payable on the first
business day following the completion of such annual audit; provided, however,
that the Consulting Fee applicable to the 2019 fiscal year shall be prorated to
cover only the time period commencing on the Commencement Date and ending on
December 31, 2019. The Consulting Fee will be payable to the Service Provider at
the same time by wire transfer in same-day funds to the bank account or accounts
designated by the Service Provider.
(b)    The parties acknowledge and agree that the Company Group’s maximization
of value for its equity holders may also include consummating (or participating
in the consummation of) one or more underwritten public offerings of any class
of equity or debt securities of the Company or any other member of the Company
Group or a direct or indirect parent company thereof pursuant to an effective
registration statement (other than on Form S-8 or a successor thereto) under the
Securities Act of 1933, as amended, or similar law in other jurisdictions (each
such offering, an “Underwritten Offering”). The services provided to the Company
Group by the Service Provider pursuant to this Agreement will help to facilitate
the consummation of an Underwritten Offering, if any member of the Company Group
decides to pursue such a transaction.
(c)    Upon presentation by the Service Provider to the Company of such
documentation as may be reasonably requested by the Company, the Company shall
reimburse (or cause to be reimbursed) the Service Provider for all reasonable
out-of-pocket expenses, including legal fees and expenses, and other
disbursements incurred by the Service Provider, its Affiliates and all of its
and its Affiliates’ Representatives in the performance of the Service Provider’s
obligations hereunder, whether incurred before, on or after the Commencement
Date, including reasonable out-of-pocket expenses incurred in connection with
(1) the Transaction Agreement and (2) any (a) Underwritten Offering or (b)
transaction (including a merger, consolidation, recapitalization or sale of
assets or equity interests) as a result of which any Person other than any
Affiliate of the Service Provider becomes the beneficial owner, directly or
indirectly, of more than 50% of the ordinary shares or other common equity and
voting securities, or all or substantially all of the assets, of the Company
Group. The parties acknowledge that such amounts shall be in addition to the
fees payable to the Service Provider pursuant to Section 4(a) of this Agreement.
Notwithstanding the foregoing, the Service Provider may instruct the Company to
pay, or cause one or more of its subsidiaries to pay, directly to any third
party any amount that would otherwise be required to be paid to the Service
Provider pursuant to the first sentence of this Section 4(c).
(d)    Nothing in this Agreement shall prohibit the Service Provider, its
Affiliates or any of its or its Affiliates’ Representatives from receiving any
other fees from the Company or any other member of the Company Group pursuant to
any other agreement or arrangement.

    
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(e)    Any portion of the fees payable to the Service Provider under this
Agreement that the Company is prohibited from paying or causing to be paid to
the Service Provider under any debt facility or credit support arrangement
(including any earn-out obligation) that the Company or any of its subsidiaries
may from time to time incur (collectively, the “Financing Agreements”) shall be
deferred and shall be payable at the earliest time permitted under the Financing
Agreements or upon the payment in full of all obligations under the Financing
Agreements. The Company shall notify the Service Provider if the Company shall
be unable to pay any fees pursuant to this Agreement on each date on which the
Company would otherwise make a payment of fees under this Agreement to the
Service Provider. Any portion of any fees not paid on the scheduled due date
shall bear interest at an annual rate equal to the yield to maturity on such
scheduled due date of the class of outstanding U.S. government bonds having a
final maturity closest to the eight-year anniversary of the Commencement Date.
(f)    All amounts payable to the Service Provider hereunder shall be paid to
the Service Provider in U.S. dollars by wire transfer in same-day funds to the
bank account or accounts designated by the Service Provider.
(g)    The Service Provider may, at its sole discretion, waive or defer, in full
or in part, payment of the Consulting Fee by providing written notice to such
effect to the Company. The Company shall not claim a deduction on any tax return
(i) for any such fee waived by the Service Provider and (ii) for any such fee
deferred by the Service Provider until actually paid to the Service Provider, if
at all.
Section 5.
Indemnification; Limitation on Damages

(a)    The Company shall indemnify and hold harmless the Service Provider, its
Affiliates, and all of the Representatives of Service Provider and its
Affiliates (other than the Company and its subsidiaries) (each such Person being
an “Indemnified Party”) from and against any and all losses, awards, claims,
demands, actions, causes of action, judgments, obligations, contracts,
agreements, debts, costs, expenses, disbursements, damages and liabilities,
whether known or unknown, contingent or otherwise, at common law, civil law and
in equity, including in connection with seeking indemnification and, whether
joint or several (the “Liabilities”), related to, arising out of or in
connection with, the services rendered by the Service Provider, the engagement
of the Service Provider pursuant to, and/or the performance by the Service
Provider (or any other Person permitted hereunder) of the services contemplated
by this Agreement, whether or not pending or threatened, whether or not an
Indemnified Party is a party, whether or not resulting in any liability and
whether or not such action, claim, demand, suit, investigation or proceeding is
initiated or brought by or on behalf of any member of the Company Group. The
Company shall reimburse any Indemnified Party for all costs, fees, disbursements
and expenses (including attorneys’ fees and expenses and fees and expenses of
any investigator or consultant) as they are incurred in connection with
investigating, preparing, pursuing, defending or assisting in the defense of any
action, claim, demand, suit, investigation or proceeding for which the
Indemnified Party would be entitled to indemnification under the terms of the
previous sentence, or any action or proceeding arising therefrom, whether or not
such Indemnified Party is a party thereto. The Company shall not be liable under
the foregoing indemnification provisions to the extent any

    
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Liability of an Indemnified Party is determined by a court of competent
jurisdiction, in a final judgment from which no further appeal may be taken, to
have resulted primarily from the willful misconduct of such Indemnified Party.
The fees, expenses, costs and disbursements of an Indemnified Party (including
attorneys’ fees and fees and expenses of any investigator or consultant) shall
be paid by the Company as they are incurred upon receipt, in each case, of an
undertaking by or on behalf of the Indemnified Party to repay such amounts if it
is finally judicially determined that the Liabilities in question resulted
primarily from the willful misconduct of such Indemnified Party.
(b)    The Company Group’s sole and exclusive remedy against the Service
Provider and any other Indemnified Party for breach of this Agreement or
otherwise arising from, in connection with or related to the performance of the
services to be rendered hereunder, shall be to offset any fees otherwise payable
to the Service Provider by the amount of any Liabilities arising out of or
relating to this Agreement or the services to be rendered hereunder, it being
understood that any recovery shall be limited to recovery of actual damages, and
no special, consequential, indirect, or punitive damages shall be allowed. No
Indemnified Party shall be liable to the Company Group (i) for any breach
hereunder by another Indemnified Party or (ii) for any breach by it, unless,
with respect to this clause (ii) only, such breach constitutes willful
misconduct as determined in a final judgment of a court of competent
jurisdiction from which no appeal can be made.
Section 6.
Notices.

All notices, requests, consents and other communications hereunder shall be in
writing and shall be deemed sufficient if personally delivered, sent by
internationally-recognized overnight courier, by facsimile or email, or by
registered or certified mail, return receipt requested and postage prepaid,
addressed as follows:
if to the Service Provider, to:
Apollo Management Holdings, L.P.
9 West 57th Street
New York, New York 10019
Attention: William B. Kuesel
Facsimile: 646-607-0528
with a copy to (which shall not constitute notice):
Sidley Austin LLP
One South Dearborn
Chicago, Illinois 60603
Facsimile: 312-853-7036
Email: pshwachman@sidley.com
Attention: Perry J. Shwachman
Email: scarney@sidley.com
Attention: Sean M. Carney
Email: asnyder@sidley.com

    
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Attention: Adam M. Snyder

if to the Company, to:
Aspen Insurance Holdings Limited
141 Front Street
Hamilton, Bermuda HM19
Facsimile: 441-295-1829
Email: Mike.Cain@aspen.co
Attention: Michael Cain

with a copy to (which shall not constitute notice):

Sidley Austin LLP
One South Dearborn
Chicago, Illinois 60603
Facsimile: 312-853-7036
Email: pshwachman@sidley.com
Attention: Perry J. Shwachman
Email: scarney@sidley.com
Attention: Sean M. Carney
Email: asnyder@sidley.com
Attention: Adam M. Snyder

or to such other address as the party to whom notice is to be given may have
furnished to each other party in writing in accordance herewith. Any such notice
or communication shall be deemed to have been received (a) in the case of
personal delivery, on the date of such delivery, (b) in the case of
nationally-recognized overnight courier, on the next business day after the date
when sent, (c) in the case of facsimile or email transmission, upon confirmation
of receipt, and (d) in the case of mailing, on the third business day following
that on which the piece of mail containing such communication is posted.
Section 7.
Benefits of Agreement.

This Agreement shall bind and inure to the benefit of the Service Provider, the
Company, the Indemnified Parties and any successors to or assigns of the Service
Provider, the Company and the Indemnified Parties; provided, this Agreement may
not be assigned by either party hereto without the prior written consent of the
other party, which consent will not be unreasonably withheld in the case of any
assignment by the Service Provider and; provided, further, that no consent of
any party shall be required for any assignment by the Service Provider to an
Affiliate of the Service Provider. Upon the Service Provider’s request, the
Company shall cause the other members of the Company Group to become direct
parties hereto.

    
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Section 8.
Governing Law; Jurisdiction.

This Agreement shall be governed by, and construed, enforced and interpreted in
accordance with, the laws of the State of New York, without giving effect to any
law that would cause the laws of any jurisdiction other than the State of New
York to be applied. Each of the parties hereto hereby (i) submits to the
exclusive jurisdiction of any state court sitting in New York City or any
federal court sitting in the Southern District of New York for the purpose of
any action arising out of or relating to this letter agreement brought by any
party hereto, (ii) agrees that all claims in respect of such action or
proceeding shall be heard and determined only in any such court, (iii) agrees
that it shall not attempt to deny or defeat such personal jurisdiction by motion
or other request for leave from any such court, (iv) agrees not to bring any
action or proceeding arising out of or relating to this letter agreement or any
of the transactions contemplated by this letter agreement in any other court and
(v) irrevocably waives, in any such action, any claim of improper venue or any
claim that such courts are an inconvenient forum.
Section 9.
Headings.

Section headings are used for convenience only and shall in no way affect the
construction of this Agreement.
Section 10.
Entire Agreement; Amendments.

This Agreement contains the entire understanding of the parties hereto with
respect to its subject matter and supersedes any and all prior or
contemporaneous agreements or understandings, and neither it nor any part of it
may in any way be altered, amended, extended, waived, discharged, modified or
terminated except by a written agreement signed by each of the parties hereto.
Section 11.
Counterparts.

This Agreement may be executed in counterparts, including via facsimile
transmission or PDF copies sent by e-mail, and each such counterpart shall be
deemed to be an original instrument, but all such counterparts together shall
constitute one and the same document.
Section 12.
Waivers.

Any party to this Agreement may, by written notice to the other party, waive any
provision of this Agreement. The waiver by any party of a breach of any
provision of this Agreement shall not operate or be construed as a waiver of any
subsequent obligation or breach.
Section 13.
Severability.

Any provision of this Agreement that is prohibited or unenforceable in any
jurisdiction will, as to such jurisdiction, be ineffective to the extent of such
prohibition or unenforceability without invalidating the remaining provisions
hereof, and any such prohibition or unenforceability in any jurisdiction will
not invalidate or render unenforceable such provision in any other jurisdiction.

    
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Section 14.
Definitions.

(a)    For purposes of this Agreement, the term “Affiliate,” with respect to the
Service Provider, shall include, without limitation, Apollo Investment Fund IX,
L.P., Apollo Overseas Partners IX, L.P., Apollo Overseas Partners (Delaware) IX,
L.P., Apollo Overseas Partners (Delaware 892) IX, L.P., Apollo Overseas Partners
(Lux) IX, SCSp, Apollo Advisors IX, L.P. and each of their respective affiliates
(collectively, the “Funds”), the general partner of each of the Funds and each
Person controlling, controlled by or under common control with any of the
foregoing Persons. Furthermore, for purposes of this Agreement, the term
“Person” shall mean an individual, partnership, limited liability partnership,
corporation, limited liability company, association, joint stock company, trust,
estate, joint venture, unincorporated organization or governmental authority (or
any department, agency or political subdivision thereof). The words “include”,
“includes” and “including” mean include, includes and including “without
limitation”. Each and every decision, election, instruction or direction to be
made or given by, or any act to be performed (or omitted) by, the Service
Provider hereunder shall be made, given, taken or omitted by the Service
Provider in its sole and non-reviewable discretion.
Section 15.
UK Carbon Reduction Commitment (“CRC”) Paying Agent Authorization

The Company acknowledges that the Service Provider, and certain companies in
which investment funds Affiliated with the Service Provider have control
(collectively with the Service Provider, the “CRC Group”), are subject to the
U.K’s Carbon Reduction Commitment Energy Efficiency Scheme. If certain of the
Company’s U.K. energy use falls within the scope of CRC, the Company will be
required under U.K. law to purchase CRC Allowances for CRC Emissions (each as
defined in the CRC Energy Efficiency Scheme Order 2013) associated with that
energy use for each annual reporting year. In addition, the Company would be
required to participate in CRC with the Service Provider’s CRC Group. In such
case, the Company acknowledges and agrees that the Service Provider may from
time to time, in its discretion, make payments to, or receive monies from, the
UK Environment Agency pursuant to CRC on the Company’s behalf. Any such action
shall be for the administrative convenience of the Company as a member of the
CRC Group, and the Company hereby authorizes, ratifies and confirms the Service
Provider’s ability to so act on the Company’s behalf as paying agent solely for
the limited purpose set forth above. The Company shall indemnify the Service
Provider in respect of any such actions on the Company’s behalf. The Service
Provider shall provide the Company with reasonable supporting documentation for
any payment made to the UK Environment Agency on the Company’s behalf.
[Signature Page Follows.]

    
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IN WITNESS WHEREOF, the parties have duly executed this Agreement as of the date
first above written.
                
ASPEN INSURANCE HOLDINGS LIMITED

By:
/s/ Mark Cloutier
Name: Mark Cloutier
Title: Group Chief Executive Officer and

Chairman

    
[Signature Page to Management Consulting Agreement]

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SERVICE PROVIDER:

APOLLO MANAGEMENT HOLDINGS, L.P.

By: Apollo Management Holdings GP, LLC,
its general partner

By:
/s/ William Kuesel
Name: William Kuesel
Title: Vice President

    

    
[Signature Page to Management Consulting Agreement]