Document:

EX-10.41

 Exhibit 10.41 
 SPLIT-DOLLAR AGREEMENT 
 THIS AGREEMENT, entered into this 28 day of January, 2013
by and between iPayment, Inc. (“The Employer”), a corporation organized and existing under the laws of the State of Delaware, and the Monaco Family Irrevocable Insurance Trust, Dated April 14, 2011,
John S. Erwin and Kurt N. Simon, trustees (“The Trust”). 
 Witnesseth: 

WHEREAS, Mark C. Monaco (“The Employee”) renders competent and faithful services on behalf of The Employer and The
Employer highly values the services, abilities and accomplishments of The Employee; and 
 WHEREAS, The Employer desires to
encourage The Employee to continue to render faithful and high quality services to The Employer; and 
 WHEREAS, The Trust
is the owner of Life Insurance Policy Number LJ7207030 (the “Policy”) insuring the life of the second to die of Mark C. Monaco and Jennifer C. Monaco (“The Insureds”) from Lincoln Life and Annuity Company
(the “Insurance Company”): and 
 WHEREAS, The Trust has assigned the Policy to The Employer as collateral
for amounts to be loaned by The Employer under this Agreement by an instrument of assignment (the “Collateral Assignment”) executed on February 27, 2013; and 

WHEREAS, The Employer is desirous of providing protection for the beneficiaries of The Insureds in the event of their untimely death, and
is willing to assist them in the payment of premiums on the Policy; and 
 WHEREAS, in exchange for the premium assistance of
The Employer, The Trust is willing to return the amounts advanced plus interest at the “Applicable Federal Rate” to The Employer, pursuant to the Collateral Assignment executed between The Trust (the
“Assignor”) and The Employer (the “Assignee”); and 
 WHEREAS, this Agreement is intended
to qualify as a Split Dollar Plan of the type described in Final Regulations issued September 11, 2003, effective September 17, 2003; and 
 NOW THEREFORE, for value received and in consideration of the mutual covenants and agreements contained herein, The Employer, for itself, its successors and assigns, and The Trust for
itself, and for its successors and assigns, agree as follows: 

 ARTICLE I 
 OWNERSHIP RIGHTS IN THE POLICY 
 A. If any individual Insured owns a majority
of the stock of The Employer, then The Trust, exclusively, shall have all of the ownership rights, options and privileges permitted by the Policy including the power to borrow against the policy value limited in amount such that
it will not impair The Employer’s interest in the Policy as described in Article I.B. below. The Employer shall be specifically prohibited from pledging the policy or withdrawing or borrowing its cash value. If no
individual Insured owns a majority of the stock of The Employer, then The Employer shall have the right to withdraw and/or borrow against its portion of the cash value. 
 B. In exchange for The Employer’s payment of its premium contributions under Article II of this Agreement, The Trust agrees that: 

 

	 	1	in the event of either of The Insureds’ death, The Employer will be paid an amount equal to the greater of (i) the cash value of The
Policy multiplied by the number of premiums that it pays divided by the total number of premiums paid or (ii) the sum of the premiums it has paid; or 

 

	 	2	in the event of any other termination of the Agreement during both of The Insureds’ lifetime, The Employer will be paid the net surrender
value of The Policy multiplied by the number of premiums that it pays divided by the total number of premiums paid. 

 At
that point, all other rights in the Policy shall belong to The Trust. 
 C. The Employer may not take any action
with respect to the Policy that will impair any right or interest of The Trust in the Policy. 
 ARTICLE
II 
 PREMIUM PAYMENT OPTIONS 
 A. The Employer shall contribute premiums under the Policy. The Employer may from time to time accelerate premium payments by paying them directly to the Insurance Company. The
Trust and/or The Employee are permitted to pay in an amount equal to the economic benefit as measured by Table 2001 and may pay additional premiums if it or they so choose. The Trust retains control of selecting the
Policy’s subaccounts, if any, if any Insured owns a majority of the stock of The Employer. If no Insured owns a majority of the stock of The Employer, then The Employer has the control of selecting the
Policy’s subaccounts, if any. 

 ARTICLE III 
 DIVISION OF DEATH PROCEEDS OF POLICY 
 In the event that either Insured shall die
while this Agreement is in force, The Employer shall be entitled to receive from the Policy proceeds an amount equal to The Employer’s interest in the Policy, as determined under Article I.B. of this
Agreement. The portion of the Policy proceeds that is in excess of the amount paid to The Employer shall be paid to the beneficiaries designated by The Trust in accordance with the terms of the Policy and
Collateral Assignment as reflected in the records of the Insurance Company. 
 ARTICLE IV 

TERMINATION OF AGREEMENT 

A. This Agreement may be terminated by The Trust at any time while both of The Insureds are living, through the delivery of
written notice of termination by the trustee to The Employer. 
 B. Upon termination of this Agreement by The Trust
while both of The Insureds are living, The Trust shall pay to The Employer in a timely fashion an amount equal to The Employer’s interest in the Policy, as determined under Article I.B. of this
Agreement in return for The Employer’s release of any claim to the Policy. 
 C. Upon division of death
proceeds of the Policy pursuant to Article III above, The Employer shall receive an amount equal to The Employer’s interest in the Policy, as determined under Article I.B. of this Agreement at which point this
Agreement shall terminate without further obligations on either party. 
 ARTICLE V 

AMENDMENT 
 This
Agreement may be amended at any time, and from time to time, by a written instrument signed by The Employer and The Trust. 
 ARTICLE VI 
 AGREEMENT BINDING UPON PARTIES 

This Agreement shall bind both The Employer, together with its successors and assigns, and The Trust, together with its successors
and assigns. 

 ARTICLE VII 
 INSURER NOT A PARTY TO AGREEMENT 
 The Insurance Company and any mutual fund shall
not be deemed a party to this Agreement. Payment or other performance of its contractual obligations in accordance with the Policy and the fund provisions shall fully discharge the Insurance Company and the mutual fund
from any and all liability. 
 ARTICLE VIII 
 CONFLICT BETWEEN COLLATERAL ASSIGNMENT AND AGREEMENT 
 In the event that there shall be any
conflict between this Agreement and the Collateral Assignment, the Collateral Assignment shall take precedence over this Agreement. 
 ARTICLE IX 
 GOVERNING LAW 

This Agreement set forth the entire agreement between the parties hereto, and any and all prior agreements are hereby superseded. The laws of the
State of New York shall govern this Agreement, without regard to any jurisdiction’s conflict of laws principles. 
 IN
WITNESS WHEREOF, the Parties hereto have set their hands on the day and year first hereinabove written. 
  

							
	 

	 		 		 	 

	  
	 		 	  

	 Monaco Family Irrevocable Life Insurance Trust
 Dated April 14, 2011
 John S. Erwin, Trustee

Kurt N. Simon, Trustee
 (“The
Trust”)
	 		 		 	Witness
	  
 iPayment, Inc.

(“The Employer”)
  
	 		 		 	

							
	By:	 	 

	 		 	 

		 	  
	 		 	  

	Name:	 	

	 		 	Witness
	Title:	 	SVP and General CounselEX-10.42

 Exhibit 10.42 

 
 

 
 Assignment Of Life Insurance Policy as Collateral 

 
  

					
	  

INSTRUCTIONS:
  
 Use this form to assign a policy(ies) as collateral for a loan. By completing this form, the Owner will transfer certain ownership rights as outlined in Section III, B to the Collateral
Assignee.
  
 Please complete this form in its entirety to avoid any delays in
processing. If you need assistance in completing this form, please call your representative, sales office, or the appropriate number listed under How to Submit this Form.
	  	 	

 	  

  

					
	The Company indicated in this section is referred to as “the Company.”	  	 x  Metropolitan Life Insurance
Company
  
  ̈  New England Life Insurance Company
  

 ̈  General American Life Insurance Company

 

 ̈  MetLife Insurance Company of
Connecticut
	  	  ̈  First MetLife Investors Insurance
Company
  
  ̈  MetLife Investors USA Insurance Company
  

 ̈  MetLife Investors Insurance Company

 

 ̈  Metropolitan Tower Life Insurance
Company

 Policy Number(s)
213017769MLU             ,                        
                 ,                       
                  
  

					
	SECTION I - About the Insured	  	 	  	 
			
	First Name	  	Middle Name	  	Last Name
	 Carl
	  	 A
	  	 Grimstad

  

			
	SECTION II - About the Collateral Assignee
		
	Name of Assignee	  	Tax ID of Assignee
	 iPayment, Inc.
	  	 62-1847043

  

	
	 Number and Street/Post Office Box
 Tower 56, 126 East 56th Street, 33rd Floor

  

							
	City	  	State	  	Zip	  	E-Mail Address
	 New York
	  	 NY
	  	 10022
	  	  

  

					
	If Assignee is a Trust, list name(s) of all currently serving trustees:
			
	First Name	  	Middle Name	  	Last Name
	  
	  	  
	  	  

			
	First Name	  	Middle Name	  	Last Name
	  
	  	  
	  	  

			
	First Name	  	Middle Name	  	Last Name
	  
	  	  
	  	  

  

  
  

					
	u  Owner Initial Here

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 SECTION III - Terms of the Assignment 

 
 A. For Value Received the undersigned hereby
assign, transfer and set over to the above Assignee, its successors and assigns (herein called the “Assignee”), the above Policies issued by the Company and any supplementary contracts issued in connection therewith (said policy and
contracts being herein called the “Policy”), upon the life of the above Insured and all claims, option, privileges, rights, title and interest therein and thereunder (except as provided in Paragraph C hereof), subject to all the terms and
conditions of the Policy and to all superior liens, if any, which the Company may have against the Policy. The undersigned by this instrument jointly and severally agree and the Assignee by the acceptance of this assignment agrees to the conditions
and provisions herein set forth. 
 B. It is expressly agreed that, without detracting from the generality of the foregoing, the following
specific rights are included in this assignment and pass by virtue hereof: 
  

	 	1.	The sole right to collect from the Company the net proceeds of the Policy when it becomes a claim by death or maturity; 

 

	 	2.	The sole right to surrender the Policy and receive the surrender value thereof at any time provided by the terms of the Policy and at such other times as the Company
may allow; 

  

	 	3.	The sole right to obtain one or more loans or advances on the Policy, either from the Company or, at any time from other persons, and to pledge or assign the Policy as
security for such loans or advances; 

  

	 	4.	The sole right to collect and receive all distributions or shares of surplus, dividend deposits or additions to the Policy now or hereafter made or apportioned thereto,
and to exercise any and all options contained in the Policy with respect thereto; provided, that unless and until the Assignee shall notify the Company in writing to the contrary, the distributions or shares of surplus, dividend deposits and
additions shall continue on the plan in force at the time of this assignment; and 

  

	 	5.	The sole right to exercise all nonforfeiture rights permitted by the terms of the Policy or allowed by the Company and to receive all benefits and advantages derived
therefrom. 

 C. It is expressly agreed that the following specific rights, so long as the Policy has not been surrendered, are
reserved and excluded from this assignment and do not pass by virtue hereof: 
  

	 	1.	The right to collect from the Company any disability benefit payable in cash that does not reduce the amount of insurance; 

 

	 	2.	The right to designate and change the beneficiary; and 

  

	 	3.	The right to elect any optional mode of settlement permitted by the Policy or allowed by the Company; but the reservation of these rights shall in no way impair the
right of the Assignee to surrender the Policy completely with all its incidents or impair any other right of the Assignee hereunder, and any designation or change of beneficiary or election of a mode of settlement shall be made subject to this
assignment and to the rights of the Assignee hereunder. 

 D. This assignment is made and the Policy is to be held as collateral
security for any and all liabilities of the undersigned, or any of them, to the Assignee, either now existing or that may hereafter arise between any of the undersigned and the Assignee with respect to the above Policy (all of which liabilities
secured or to become secured are herein called “Liabilities”). 
 E. The Assignee covenants and agrees with the undersigned as
follows: 
  

	 	1.	That any balance of sums received hereunder from the Company remaining after payment of the then existing Liabilities, matured or unmatured, shall be paid by the
Assignee to the persons entitled thereto under the terms of the Policy had this assignment not been executed; 

  

	 	2.	That the Assignee will not exercise either the right to surrender the Policy or (except for the purpose of paying premiums) the right to obtain policy loans from the
Company, until there has been default in any of the Liabilities or a failure to pay any premiums when due, nor until twenty days after the Assignee shall have mailed, by first-class mail, to the undersigned at the addresses last supplied in writing
to the Assignee specifically referring to this assignment, notice of intention to exercise such right; and 

  

	 	3.	That the Assignee will upon request forward without unreasonable delay to the Company the Policy for endorsement of any designation or change of beneficiary or any
election of an optional mode of settlement. 

 F. The Company is hereby authorized to recognize the Assignee’s claims to the
rights hereunder without investigation the reason for any action taken by the Assignee, or the validity of the amount of the Liabilities or the existence of any default therein, or the giving of any notice under Paragraph E (2) above or
otherwise, or the application to be made by the Assignee of any amounts to be paid to the Assignee. The sole signature of the Assignee shall be sufficient of the exercise of any rights under the Policy assigned hereby and the sole receipt of the
Assignee for any sums received shall be a full discharge and release therefore to the Company. Checks for all or any part of the sums payable under the Policy and assigned herein, shall be drawn to the exclusive order of the Assignee if, when, and
in such amounts as may be, requested by the Assignee. 
 G. The Assignee shall be under no obligation to pay any premium, or the principal of or
interest on any loans or advance on the Policy whether or not obtained by the Assignee, or any other charges on the Policy, but any such amounts so paid by the Assignee from its own funds, shall become a part of the Liabilities hereby secured, shall
be due immediately, and shall draw interest at the annual percentage rate then in effect for the note or other evidence of liability. 

  
  

					
	u  Owner Initial Here

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 H. The exercise of any right, option, privilege or power given herein to the Assignee shall be at the option
of the Assignee, but (except as restricted by Paragraph E (2) above) the Assignee may exercise any such right, option, privilege or power without notice to, or assent by, or affecting the liability of, or releasing any interest hereby assigned
by the undersigned, or any of them. 
 I. The Assignee may take or release other security, may release any party primarily or secondarily liable
for any of the Liabilities, may grant extensions, renewals or indulgences with respect to the Liabilities, or may apply to the Liabilities in such order as the Assignee shall determine, the proceeds of the Policy hereby assigned or any amount
received on account of the Policy by the exercise of any right permitted under this assignment, without resorting or regard to other security. 

J. In the event of any conflict between the provisions of this assignment and provisions of the note or other evidence of any Liability, with respect to
the Policy or rights of collateral security therein, the provisions of this assignment shall prevail. 
 K. Each of the undersigned declares
that no proceedings in bankruptcy are pending against him and that his property is not subject to any assignment for the benefit of creditors. 

Signatures 
  

All Owners are required to sign this form. Any Irrevocable Beneficiary must sign this form. 

Please sign as shown below: 
  

			
	A Partnership	  	The signature and title of one authorized partner (other than the Insured).
		
	A Sole Proprietorship	  	The full name of the business should be printed with the signature of the owner followed by the word “sole owner.”
		
	A Trust	  	Signatures, followed by the word “Trustee,” of all required Trustees. Also submit a Trust Certification, which is available from your representative, sales office, or the
appropriate number listed under How to Submit this Form.
		
	A Corporation	  	The signature and title of one officer (other than the Insured).
		
	An Individual acting on behalf of the Owner	  	The full name of the Owner’s fiduciary or agent and the legal documentation of the authority to act (e.g., power of attorney, guardianship papers, etc.).

  

					
	Type of
Owner:     ̈  Individual    x  Trust	  	 ̈ Corporation or Partnership	  	 Tax ID or Social Security Number
 ###-##-####

  

			
	 Name of Trust, Corporation or Partnership
 The Carl A Grimstad 2013 Insurance Trust I
	  	 Date of Trust 1/25/2013

  

											
	u	 	 Signature
 

    
	  		  		  	 Date

3/4/13
	  	 Title (If you are acting in a representative capacity) 
 Trustee

		 	  
	  	  
	  	  

						
		 	Printed Name - First	  	Middle	  		  		  	Last
				
		 	 J. Daniel
	  	  
	  	 Schmidt

						
	u	 	 Signature of Witness
 

    
	  		  		  		  	 Date
  
 3/4/13

		 	  
	  	  

						
		 	Printed Name - First	  	Middle	  		  		  	Last
				
		 	

    	  		  	

    
		 	  
	  	  
	  	  

											
						
	 Number and Street/Post Office Box of Owner

Tower 56, 126 East 56th Street, 33rd Floor
	  	 	  	 	  	 	  	 	  	 
						
	City	  		  		  	State	  	Zip	  	E-Mail Address
	 New York
	  	 NY
	  	 10022
	  	  

  

  
  

					
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	Type of Co-Owner:  ̈ Individual   ̈ Trust	  	 ̈ Corporation or Partnership	  	 Tax ID or Social Security Number
     

					
			
	 Name of Trust, Corporation or Partnership

    
	  	 	  	 Date of Trust
  

  

									
		 	Signature of Co-Owner	  		  	Date	  	Title (If you are acting in a representative capacity)
	u	 	  
	  	  
	  	  

		 	Printed Name - First	  	Middle	  		  	Last
		 	  
	  	  
	  	  

		 	Signature of Witness	  		  		  	Date
	u	 	  
	  	                    
		 	Printed Name - First	  	Middle	  		  	Last
		 	  
	  	  
	  	  

  

	
	 Beneficiary’s signature is necessary only if beneficiary is irrevocably designated or if required by assignee.

 
 Type of
Beneficiary:     ̈ Individual x
Trust         ̈ Corporation or Partnership

  

			
	 Name of Trust, Corporation or Partnership
  

The Carl A Grimstad 2013 Insurance Trust I
	  	 Date of Trust
 1/25/2013

  

									
	u	 	 Signature of Beneficiary
 

	  	 Date
  
 3/4/13
	  	 Title (if you are acting in a representative capacity)

 
 Trustee

		 	  
	  	  
	  	  

					
		 	Printed Name - First	  	Middle	  		  	Last
				
		 	 J Daniel
	  	  
	  	 Scmidt

					
		 	Signature of Witness	  		  		  	Date
	u	 	 

	  	 3/4/13

					
		 	Printed Name - First	  	Middle	  		  	Last
		 	

    	  		  	

    
		 	  
	  	  
	  	  

							
		
	 Type of Beneficiary:      ̈ Individual
     ̈ Trust          ̈ Corporation or Partnership

 
 Name of Trust, Corporation or Partnership
	  	Date of Trust
	  
	  	  

  

											
		 	Signature of Beneficiary	  		  	Date	  	Title (If you are acting in a representative capacity)
	u	 	  
	  	  
	  	  

						
		 	Printed Name - First	  	Middle	  		  	Last	  	
		 	  
	  	  
	  	  

						
		 	Signature of Witness	  		  		  	Date	  	
	u	 	  
	  	  
	  	
						
		 	Printed Name - First	  	Middle	  		  	Last	  	
		 	  
	  	  
	  	  

  

  
  

					
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