Document:

EX-10.6.1

 Exhibit 10.6.1 

SUBORDINATED PROMISSORY NOTE 

Brookfield, WI 
 January 15,
2013 
 FOR VALUE RECEIVED, Connecture, Inc. (hereinafter, the “Maker”), promises to pay to Randall P. Herman, on behalf of
and for the benefit of the Stockholders (“Payee”), the principal sum of Three Million Dollars ($3,000,000), as adjusted pursuant to the terms hereof, together with any and all other sums which may be owing to Payee by Maker pursuant
to this Subordinated Promissory Note (this “Note”). 
 1. Defined Terms. Capitalized terms used but not defined
herein shall have the meanings given to them in that certain Agreement and Plan of Merger (the “Merger Agreement”), dated as of January 14, 2013, among Maker, DestinationRx, Inc., DRX Acquisition Company, the persons and
entities listed as Principal Stockholders on the signature pages thereto, and Payee, solely in its capacity as Representative of the Stockholders (together with and any successor Representative pursuant to the Merger Agreement,
“Representative”). 
 2. Escrow of Note. This Note is delivered pursuant to Section 3.4(a)(ii) of the Merger
Agreement. This Note, and the proceeds from the payment of this Note, are to be held in escrow by U.S. Bank National Association, a national banking association (the “Escrow Agent”), to be disbursed to the Stockholders, cancelled or
adjusted in accordance with the Merger Agreement and the Escrow Agreement. 
 3. Payment Terms. Except as otherwise provided herein,
the outstanding principal amount of this Note, together with accrued interest, will be paid in one lump sum payment on January 15, 2015 (the “Maturity Date”), unless the Maturity Date is extended by mutual agreement of Maker
and Representative. Whenever any payment to be made under this Note shall be due on a day that is not a Business Day, such payment shall be due on the next succeeding Business Day. All payments on this Note shall be applied first to other charges
due under this Note (if any), second to payment of principal, if any, and then to payment of accrued interest. 
 4. Interest Rate.
During the period from the date hereof until all sums due hereunder have been paid in full, simple interest shall accrue on the unpaid principal amount of this Note at a per annum rate of eight percent (8%); provided, however, that no interest shall
accrue or be payable for any time period during which there is a dispute regarding Damages payable pursuant to Article X of the Merger Agreement. 

5. Prepayment. Maker shall have the right to prepay all or part of the principal, accrued and unpaid interest or other amounts payable
hereunder, at any time and from time to time. A partial prepayment shall not otherwise change the Maturity Date herein. 
 6.
Adjustments. Upon final resolution of the Closing Date Working Capital Adjustment pursuant to Section 3.5 of the Merger Agreement, the principal amount of this Note will be (i) increased by the amount of the Working Capital
Adjustment Excess or (ii) reduced by 

 
the amount of the Working Capital Adjustment Shortfall, and interest shall be deemed to have accrued on this Note at such adjusted principal amount from the date hereof. Upon final resolution of
a claim for Damages by an Indemnified Party under Article X of the Merger Agreement which is to be satisfied out of the Escrow Deposit pursuant to the terms of the Merger Agreement, the outstanding principal amount of this Note shall be reduced by
such amount in satisfaction of such claim. 
 7. Manner And Method Of Payment. All payments called for in this Note shall be made in
lawful money of the United States of America. 
 8. Events of Default. Upon the occurrence of (each of the following, an
“Event of Default”) (i) any failure of Maker to pay when due any amount owing under this Note, (ii) a Change of Control Event (as defined below), (iii) a Sale of DRX (as defined below), (iv) a petition for
bankruptcy is filed by Maker voluntarily or involuntarily against Maker and the petition is not dismissed within 60 calendar days of the date of the filing thereof; or (v) Maker makes an assignment for the benefit of creditors, then the entire
principal amount and accrued interest shall become due and payable at the election of Representative following written notice to Maker from Representative; 

For purposes of this Note, a “Change of Control Event” shall mean any merger or consolidation in which (i) Maker is a
constituent party or (ii) a subsidiary of Maker is a constituent party and Maker issues shares of its capital stock pursuant to such merger or consolidation, in each case except any such merger or consolidation involving Maker or a subsidiary
in which the shares of capital stock of Maker outstanding immediately prior to such merger or consolidation continue to represent, or are converted into or exchanged for shares of capital stock that represent, immediately following such merger or
consolidation, a majority, by voting power or value, of the capital stock of (A) the surviving or resulting entity or (B) if the surviving or resulting entity is a wholly-owned subsidiary of another entity immediately following such merger
or consolidation, the parent entity of such surviving or resulting entity. 
 For purposes of this Note, a “Sale of DRX”
shall mean the sale, transfer, exclusive license or other disposition, in a single transaction or series of related transactions, by Maker of all or substantially all of the assets of the Surviving Company in the Merger, or the sale or disposition
(whether by merger or otherwise) of all of the capital stock of the Surviving Company in the Merger, in each case to a third party that is unrelated to Maker. 

9. Subordination. Maker and Representative covenant and agree that this Note and the indebtedness evidenced hereby shall be subject and
subordinate to the prior indefeasible payment in full in cash of any indebtedness for borrowed money of Maker which is designated as such by written notice from Maker to Representative, including the existing indebtedness for borrowed money of Maker
to Wells Fargo and Harbert Mezzanine Partners II SBIC, L.P. pursuant to that certain Loan and Security Agreement, dated as of February 16, 2011 (as amended, restated or otherwise modified from time to time, the “Harbert Credit
Agreement” ), among Maker, its subsidiaries and Harbert Mezzanine Partners II SBIC, L.P. (the “Harbert Facility”) and all indebtedness pursuant to that certain Credit Agreement, dated as of January 15, 2013 (as
amended, restated or otherwise modified from time to time, the “Wells Credit  

  
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 Agreement” ), among Maker, the other credit parties signatory thereto and Wells Fargo Bank, National
Association, as agent (the “Wells Facility” and together with the Harbert Facility, and in each case, any refinancings or replacements of the foregoing, collectively, the “Senior Indebtedness”); that any liens and
security interests of the holders of Senior Indebtedness in any collateral, now or hereafter acquired, securing all or any portion of the Senior Indebtedness shall be senior, regardless of the time or method of perfection, to all liens and security
interests, if any, of Payee (or any agent therefor) in the collateral, if any, securing all or any portion of the obligations hereunder; that the subordination is for the benefit of, and shall be enforceable directly by, the holders of Senior
Indebtedness, and that each holder of Senior Indebtedness shall be deemed to have acquired Senior Indebtedness in reliance upon the covenants and provisions contained in this Note. Until the Senior Indebtedness has been indefeasibly paid in full in
cash, neither Maker nor any other person or entity on its behalf (other than payments by the guarantors under the Subordinated Note Guaranty (as such term is defined in the Merger Agreement)) shall make any payment of any kind or character
(including without limitation, payments of interest or principal made at any time, including on the maturity date or otherwise) with respect to any obligations on this Note without the express written consent of the holders of the Senior
Indebtedness; provided, however, Maker shall be permitted to make payment of interest and payments of principal at the Maturity Date (without the consent of the holders of Senior Indebtedness) so long as there is no event of default under the Wells
Facility (before and after giving effect to such payment) and (i) with respect to scheduled interest payments, excess availability plus qualified cash under the Wells Facility is at least $2,500,000 or (ii) with respect to payments of
principal at the Maturity Date, excess availability plus qualified cash under the Wells Facility is at least $5,000,000, in each case after giving effect to such payment. In the event that any payment is received by Payee in violation of the
provisions hereof, such payment shall be held in trust for the benefit of, and shall be paid over or delivered to, the holders of Senior Indebtedness for application to the payment of Senior Indebtedness. In addition, until the Senior Indebtedness
has been indefeasibly paid in full in cash, Payee shall not take any collection action or enforcement action, or exercise any rights or remedies, with respect to this Note. The rights and obligations of Maker and Payee of this Note shall be
enforceable by a decree of specific performance issued by any court of competent jurisdiction, and appropriate injunctive relief may be applied for and granted in connection therewith. Such remedies shall, however, be cumulative and not exclusive
and shall be in addition to any other remedies which any party may have under this Note or otherwise. Payee agrees that it will execute further subordination agreements, documents and instruments and take such further actions reasonably requested by
any senior creditor that further the purposes and provisions of this Section 9. 
 10. Waivers. Maker hereby waives presentment
for payment, demand, protest, notice of protest, notice of dishonor and notice of nonpayment of this Note. 
 11. Restriction of Payments. So
long as any amounts remain outstanding under this Note, Maker shall not make any distributions or pay any dividends on account of equity to its stockholders, or make payments on junior indebtedness for borrowed money of Maker held by its
stockholders, without the prior written consent of Representative. 
 12. Representative. Payee, as Representative for the
Stockholders, shall have the right to enforce this Note for the benefit of and on behalf of the Stockholders. 

  
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 13. Modifications. This Note cannot be amended or changed except in writing signed by
Maker and Representative and the holders of the Senior Indebtedness, and no waiver of any term or condition of this Note shall be effective except by a writing duly executed by Representative. 

14. Binding Nature. Except as otherwise provided herein, this Note shall be binding upon and shall inure to the benefit of the parties
hereto and their respective heirs, legatees, beneficiaries, personal representatives and other legal representatives, successors and assigns. 

15. Invalidity Of Any Part. If any provision or part of any provision of this Note shall for any reason be held invalid, illegal or
unenforceable in any respect, such invalidity, illegality or unenforceability shall not affect any other provisions of this Note and this Note shall be construed as if such invalid, illegal or unenforceable provision or part thereof had never been
contained herein, but only to the extent of its invalidity, illegality or unenforceability. 
 16. Choice Of Law; Consent To Venue And
Jurisdiction. This Note shall be governed, construed and interpreted strictly in accordance with the laws of the State of Delaware. In the event that any Party commences a lawsuit or other proceeding relating to or arising from this Note, the
Parties absolutely and irrevocably consent and submit to the jurisdiction and venue of the courts in the State of Delaware and of any Federal court located in the State of Delaware in connection with any actions or proceedings brought against any of
the Parties (or each of them) arising out of or relating to this Note. The Parties consent to and agree to submit to the jurisdiction of any of the courts specified herein and agree to accept service of process to vest personal jurisdiction over
them in any of these courts. 
 17. Assignment. This Note may not be assigned by Payee without the prior written consent of Maker.
Maker may not assign any of its obligations under this Note without the prior written consent of Payee. 
 18. Notices. Any notice,
request, demand or other communication required or permitted hereunder among shall be in accordance with the notice provisions of the Escrow Agreement. 

19. Third Party Beneficiaries. Harbert Mezzanine Partners II SBIC, L.P. and Wells Fargo Bank, National Association are intended third
party beneficiaries of Section 9 of this Note in connection with the extension of credit pursuant to the Senior Indebtedness. 
 20.
Entire Agreement. This Note constitutes the entire agreement between the parties hereto with respect to the subject matter hereof. 

[SIGNATURE PAGE FOLLOWS] 

  
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 IN WITNESS WHEREOF, Maker has executed this Subordinated Promissory Note as of
January 15, 2013. 
  
  

			
	MAKER:
	
	CONNECTURE, INC.
		
	By	 	 /s/ Robert Douglas Schneider

	Name:	 	Robert Douglas Schneider
	Title:	 	CEO

  

			
	ACCEPTED AND AGREED:
	
	Randall P. Herman, in his capacity as Representative
		
	By	 	 /s/ Randall P. Herman

	Name:	 	Randall P. Herman
	Title:	 	

  
 5EX-10.6.2

 Exhibit 10.6.2 

SUBORDINATED NOTE GUARANTY 

THIS SUBORDINATED NOTE GUARANTY (the “Guaranty”) is made as of January 15, 2013 by GPP-Connecture, LLC
(“GPP”) and Chrysalis Ventures II, L.P. (“Chrysalis”) (collectively with GPP, the “Guarantors”; sometimes each individually, a “Guarantor”) for the
benefit of Payee (as defined in the Note) (the “Payee”). 
 RECITALS: 

A. Pursuant to that certain Agreement and Plan of Merger, dated as of January 14, 2013, by and among Connecture, Inc.
(“Maker”), DestinationRx, Inc., DRX Acquisition Company, Inc., the Principal Stockholders (as defined therein) and the Representative (as defined therein) (the “Merger Agreement”), Maker issued to the
Representative (on behalf of the Stockholders) a subordinated promissory note (the “Note”) in the principal amount of $3,000,000 as may be adjusted pursuant to the terms of the Merger Agreement. Capitalized terms used herein
and not otherwise defined shall have the meanings ascribed to them in the Note. 
 B. To induce Payee to accept the Note, Guarantors have
agreed with Payee to unconditionally guaranty the prompt payment of principal (subject to Section1(c)) provided for in the Note pursuant to the provisions thereof. 

C. Guarantors own direct or indirect interests in Maker, and will benefit from the acceptance of the Note by Payee. To further induce
Guarantors, the Payee has agreed that all interest otherwise payable under the Note shall be paid to the Guarantors as set forth in Section 1(c). 

D. Guarantors have agreed to give such guaranty to Payee as provided herein. 

NOW, THEREFORE, in consideration of the premises and for the purpose of inducing Payee to accept the Note, Guarantors agree as follows: 

1. Guaranty. 
 a.
Guarantors hereby severally guarantee the following (collectively, the “Guaranteed Obligations”): the due and prompt payment of (i) the principal of the Note, as adjusted pursuant to the terms of the Merger
Agreement, and all other monies (other than interest) due or which may become due thereon (including but not limited to any costs of collection or costs of enforcing this Guaranty); and (ii) the due and prompt performance and observance of all
terms, covenants and conditions agreed to be performed by the Maker under the Note, whether according to the present terms thereof, at any earlier or accelerated date or dates as provided therein, or pursuant to any extension of time or to any
change or changes in the terms, covenants and conditions thereof now or at any time hereinafter made or granted. Each of the Guarantors hereby agrees that this Guaranty is an absolute, irrevocable and unconditional guaranty of payment and is not a
guaranty of collection. 

 b. The Guarantors’ liability for payment of the Guaranteed Obligations is several and not
joint and several. The percentage of the Guaranteed Obligations to which each Guarantor is liable is as follows: 
  

					
	 GPP
	  	 	66.67	% 
	 Chrysalis
	  	 	33.33	% 

 c. As consideration for the agreement to this Guaranty, Payee agrees that any interest on the Note shall be
payable to the Guarantors in the proportions set forth in Section 1(b). For avoidance of doubt, Payee hereby agrees that Maker will make such interest payments directly to Guarantors. 

2. Liability. Each Guarantor shall pay its percentage of the Guaranteed Obligations to Payee within twenty (20) days after
written notice by Payee of the occurrence and continuance of any Event of Default under the Note, without taking any prior action or proceeding of any kind to enforce the Note other than requesting payment thereof by Maker, if required, in
accordance with the terms thereof. 
 3. Representations and Warranties. Each Guarantor for itself only represents and
warrants to Payee that: 
 a. It (i) is a corporation, partnership or limited liability company duly incorporated or
organized, as the case may be, validly existing and in good standing under the laws of its jurisdiction of incorporation or organization, (ii) is duly qualified to do business as a foreign entity and is in good standing (to the extent such
concept is applicable) under the laws of each jurisdiction where the business conducted by it makes such qualification necessary, except where the failure to be so qualified would not have a material adverse effect on such Guarantor being able to
perform its obligations under this Guaranty and (iii) has all requisite corporate, partnership or limited liability company power and authority, as the case may be, to own, operate and encumber its property and to conduct its business in each
jurisdiction in which its business is conducted or proposed to be conducted. 
 b. It has the requisite corporate, limited
liability company or partnership, as applicable, power and authority and legal right to execute and deliver this Guaranty and to perform its obligations hereunder. The execution and delivery by it of this Guaranty and the performance of its
obligations hereunder have been duly authorized by proper corporate, limited liability company or partnership proceedings, including any required shareholder, member or partner approval, and this Guaranty constitutes a legal, valid and binding
obligation of such Guarantor, enforceable against such Guarantor, in accordance with its terms, subject to any applicable bankruptcy, insolvency or similar laws whether in a proceeding in law or in equity. 

  
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 c. Neither the execution and delivery by it of this Guaranty, nor the
consummation by it of the transactions herein contemplated, nor compliance by it with the terms and provisions hereof, will (i) conflict with the charter or other organizational documents of such Guarantor, (ii) conflict with, result in a
breach of or constitute (with or without notice or lapse of time or both) a default under any law, rule, regulation, order, writ, judgment, injunction, decree or award applicable to such Guarantor or any provisions of any indenture, material
instrument or material agreement to which the Guarantor is party or is subject or by which it or its property is bound or affected, or require termination of any such indenture, instrument or agreement, or (iii) require any approval of such
Guarantor’s board of directors, shareholders, members, partners or unitholders except such as have been obtained. 
 d.
The execution, delivery and performance by such Guarantor of this Guaranty or any of the documents related hereto or contemplated herein does not and will not require any registration with, consent or approval of, or notice to, or other action to,
with or by any governmental authority, or any third-party, except filings, consents or notices which have been made. 
 e. Review of
Documents. Guarantor has examined the Note. 
 f. Binding Obligation. This Guaranty constitutes the valid and legally binding
obligation of Guarantor, and is fully enforceable against Guarantor in accordance with its terms. 
 g. Litigation. There are no
actions or proceedings pending or, to Guarantor’s knowledge, threatened before any court or administrative agency which would materially and adversely affect the financial condition of Guarantor or the authority of Guarantor to enter into, or
the validity or enforceability of, this Guaranty. 
 h. No Conflicting Agreements. There is no provision of any agreement, contract,
or law, binding on Guarantor or affecting any of its property, which would materially conflict with or in any way prevent the execution, delivery of performance of the terms of this Guaranty, or which would be in material default or materially
violated as a result of such execution, delivery or performance. 
 4. Covenant. Each Guarantor shall maintain, at all times,
cash, other liquid assets or Unfunded Capital Commitments sufficient to pay such Guarantor’s several portion of the Guaranteed Obligations. Each Guarantor shall deliver evidence of such financial wherewithal to Payee upon reasonable request.
For purposes hereof, “Capital Commitments” shall mean, with respect to such Guarantor, the aggregate capital contributions that may be required to be made by the limited partners of such Guarantor under such Guarantor’s
partnership agreement, and “Unfunded Capital Commitments” shall mean, with respect to such Guarantor, the excess of (i) the Capital Commitments plus (ii) the amount of any distributions received by the limited partners
that may be recalled by such Guarantor under the Guarantor’s partnership agreement over the aggregate amounts of capital contributions previously made by the limited partners to such Guarantor. 

  
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 5. Severability. In case any provision (or any part of any provision) set forth in
this Guaranty shall for any reason be held to be invalid, illegal or unenforceable in any respect, such invalidity, illegality or unenforceability shall not affect any other provision (or remaining part of the affected provision) of this Guaranty,
but this Guaranty shall be construed as if such invalid, illegal or unenforceable provision (or any part thereof) had never been contained herein, but only to the extent it is invalid, illegal or unenforceable. 

5. Choice Of Law; Consent To Venue And Jurisdiction. This Guaranty shall be governed, construed and interpreted strictly in
accordance with the laws of the State of Delaware. In the event that any party commences a lawsuit or other proceeding relating to or arising from this Guaranty, the parties absolutely and irrevocably consent and submit to the jurisdiction and venue
of the courts in the State of Delaware and of any Federal court located in the State of Delaware in connection with any actions or proceedings brought against any of the parties (or each of them) arising out of or relating to this Guaranty. The
parties consent to and agree to submit to the jurisdiction of any of the courts specified herein and agree to accept service of process to vest personal jurisdiction over them in any of these courts. 

6. Notices. All notices, requests, demands, claims, and other communications hereunder will be in writing. Any notice, request,
demand, claim, or other communication hereunder shall be deemed duly given (a) when delivered personally to the recipient, (b) when sent by electronic mail or facsimile, on the date of transmission to such recipient, (c) one business
day after being sent to the recipient by reputable overnight courier service (charges prepaid), or (d) four business days after being mailed to the recipient by certified or registered mail, return receipt requested and postage prepaid, and
addressed to the intended recipient as set forth on Exhibit A. 
 7. Successors and Assigns. This Guaranty shall inure
to the benefit of and be enforceable by Payee and Payee’s successors and assigns. 
 8. Counterparts. This Guaranty may
be executed in any number of counterparts, each of which shall be an original but all of which, together, shall constitute one and the same instrument. 

10. Term of Guaranty. This Guaranty shall continue in full force and effect with regard to each Guarantor and shall not be
discharged or released until such time as such Guarantor’s several portion of the Guaranteed Obligations set forth in Section 1 above and all other sums payable by such Guarantor hereunder are paid in full. 

11. Final Agreement and Amendments. This Guaranty, together with the Note, constitute the final and entire agreement and
understanding of the parties, and any term, condition, covenant or agreement not contained herein or therein is not a part of the agreement and understanding of the parties. Neither this Guaranty, nor any term, condition, covenant or agreement
hereof may be changed, waived, discharged or terminated orally, but only by an 

  
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instrument in writing signed by the party against whom enforcement of the change, waiver, discharge or termination is sought. Nothing in this Guaranty shall convey any rights upon any person or
entity which is not a party or an assignee of a party to this Agreement 
 [REMAINDER OF PAGE INTENTIONALLY BLANK] 

  
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 IN WITNESS WHEREOF, the parties have executed and delivered this Guaranty as of the day and year
first above written. 
  

					
	GUARANTORS:
	
	GPP – CONNECTURE, LLC
		
	By:	 	 /s/ Adam Dolder

	Title:	 	President
	
	CHRYSALIS VENTURES II, L.P.
		
	By:	 	CHRYSALIS PARTNERS II, LLC, its General Partner
			
		 	By:	 	 /s/ David A. Jones, Jr.

		 	Title:	 	 Member

	
	PAYEE
		
	By	 	 /s/ Randall P. Herman

	Name:	 	Randall P. Herman
	
	Agreed and Acknowledged:
	
	Connecture, Inc.
		
	By	 	 /s/ James Purko

	Name:	 	James Purko
	Title:	 	Chief Financial Officer

  
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 Exhibit A 

Contact Information for Notices 

Payee 
 Randall P. Herman 

Pine Grove Management, LLC 
 2150 Accenture Tower 

333 South Seventh Street 
 Minneapolis, MN 55402 

Fax: (612) 436-8320 
 Email: rherman@pchi.net 

GPP 
 GPP—Connecture, LLC 

c/o Great Point Partners, LLC 
 165 Mason Street, 3rd Floor 

Greenwich, CT 06830 
 Attention: Brett Carlson 

Fax: (203) 971-3320 
 Email: bcarlson@gppfunds.com

 Chrysalis 
 Chrysalis Ventures II, L.P. 

101 South Fifth Street 
 Suite 1650 

Louisville, KY 40202-3122 
 Attention: David A. Jones, Jr. and
Alan Ying 
 Fax: (502) 583-7648 
 Email:
DJones@ChrysalisVentures.com 
 And AYing@ChrysalisVentures.com 

Connecture, Inc. 
 Connecture, Inc. 

18500 W. Corporate Drive, Suite 250 
 Brookfield, Wisconsin 53045

 Fax: (262) 432-0075 
 Attn: Doug Schneider 

Electronic mail: Dschneider@connecture.com

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