Document:

EX-10.10.5

 Exhibit 10.10.5 

SEPARATION PAY AGREEMENT 
 THIS
SEPARATION PAY AGREEMENT (the “Agreement”), by and between Connecture, Inc. (the “Company”) and Douglas Schneider (“You”)(the Company and You each a “Party”, collectively the “Parties”), is entered
into and made effective as of December 31, 2011 (the “Effective Date”). 
 WHEREAS, the Company and You have agreed to the terms of the
separation pay the Company will pay You upon the termination of Your employment, and the Parties desire to express the terms and conditions in this Agreement. 

NOW, THEREFORE, in consideration of Company’s agreement to employ You and in further consideration of the mutual agreements set forth herein, it is
agreed: 
 1) EMPLOYMENT PERIOD. Your employment relationship with the Company is at-will. You may terminate Your employment with the Company
at any time and for any reason whatsoever simply by notifying the Company. Likewise, the Company may terminate Your employment at any time with or without cause or advance notice. The period during which You are employed by the Company shall be
referred to as the “Employment Period.” 
 2) TERMINATION. Your employment may be terminated for any or no reason, including any of
the following: 
  

	 	a)	Your death; 

  

	 	b)	Your disability which renders You unable to perform the essential functions of Your job even with reasonable accommodation; 

  

	 	c)	Mutual agreement between You and the Company at any time; 

  

	 	d)	For Cause. For Cause means: 

  

	 	i)	Willful insubordination; 

  

	 	ii)	Any act or omission by You which is, or is likely to be, intentionally injurious to the Company or the business reputation of the Company; 

 

	 	iii)	Your willful misconduct, dishonesty, fraud, or malfeasance that results in injury to the Company; or 

  

	 	iv)	Your arrest, indictment for, or conviction of, or Your entry of a plea of guilty or no contest to: (a) a felony, or (b) crime involving moral turpitude; 

 

	 	e)	Your resignation for any or no reason, other than for Good Reason. If You resign Your employment with the Company, You shall provide the Company with thirty (30) days advance written notice of such resignation (the
“Notice Period”); provided, however, that the Company may, at any time during the Notice Period, terminate Your employment for any or no reason. If the Company terminates Your employment for any reason prior to the expiration of the Notice
Period, then: (i) the Company will pay You all accrued but unpaid wages through the date of termination based on Your then current base salary, and (ii) such termination shall still be considered a resignation under this Section 2(e).
Nothing in this Section 2(e) shall alter the at-will employment relationship between You and the Company as set forth in Section 1 above; or 

  

	 	f)	Without Cause. Without Cause means any termination of employment by the Company which is not defined in Sections 2(a) - 2(e) above. 

 

	 	g)	 Good Reason. Good Reason means Your resignation if: (i) the Company, without Your written consent, (a) materially reduces Your then
current authority, duties, or responsibilities, (b) materially reduces Your then current base salary, unless substantially all other executive management employees’ base salary is similarly or proportionately reduced, or
(c) materially changes the geographic location at which You must perform services for the Company; (ii) You provide written notice to the Company of any such action 

  
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within sixty (60) days of the date on which such action first occurs and provide the Company with thirty (30) days to remedy such action (the “Cure Period”); (iii) the
Company fails to remedy such action within the Cure Period, and (iv) You resign within ten (10) days of the expiration of the Cure Period. Good Reason shall not include any isolated, insubstantial, or inadvertent action that (a) is
not taken in bad faith, and (b) is remedied by the Company within the Cure Period. 

 3) Obligations of Company on
Termination of Employment.  
  

	 	a)	If this Agreement terminates for any of the reasons set forth in Sections 2(a) – 2(e) above, then all of the Company’s obligations hereunder shall immediately cease and terminate, and You shall thereupon have
no further right or entitlement to additional salary, incentive compensation payments or awards, or any perquisites from the Company whatsoever, except for the payment of Your then current base salary through the date of termination.

  

	 	b)	If this Agreement terminates as described in Section 2(f) or Section 2(g) above, then the Company shall pay to You all accrued but unpaid wages through the termination date based on Your then current base
salary. In addition, after Your “separation from service” (as defined in Code §409A(a)(2)(A)(i)) from the Company, the Company shall (i) pay You an amount equal to nine (9) months of Your then current annual base salary, to
be paid over a period of nine (9) months on the first day of each month, in equal installments (each a “Salary Installment”), beginning on the first day of the next month immediately following the expiration of the 60-Day Release
Period (defined below), and (ii) reimburse Your and Your eligible dependents’ actual Consolidated Omnibus Budget Reconciliation Act (“COBRA”) premium under the Company’s major medical group health plan on a monthly basis for
a period of nine (9) months. If the first day of the month falls on a weekend or a legal holiday, the respective Salary Installment will be paid on the business day immediately preceding such day. Except as provided in the previous sentence,
under no circumstances may any Salary Installment to be made under this Section 4(b) be accelerated or deferred unless agreed to in writing by Company and You. 

The separation payments set forth in this Section 4(b) are subject to applicable withholdings, including, but not limited to, withholdings
required by Code §3401. Except as provided in this Section 4(b), the Company shall have no further obligations to You, including under this Agreement, Company policy, or otherwise. The separation payments set forth in this
Section 4(b) shall constitute full satisfaction of the Company’s obligations under this Agreement. The Company’s obligation to provide the separation payments set forth in this Section 4(b) shall be conditioned upon:
(i) Your execution and non-revocation of an effective Separation & Release Agreement in a form prepared by and satisfactory to the Company, which includes, but is not limited to, Your release of the Company from any and all liability
and claims of any kind (provided that such agreement must be executed and become irrevocable within sixty (60) days after the date of Your “separation from service” (the “60 Day Release Period”)), and (ii) Your
compliance with the restrictive covenants set forth in the Employment Covenants Agreement between You and the Company dated January 2, 2012 (the “ECA”), and all other post-termination obligations to which You may be subject,
including, but not limited to, the obligations contained in this Agreement. If You do not execute, or if You execute and then revoke, a Separation & Release Agreement as set forth above, the Company shall have no obligation to provide any
separation payments to You under this Section 4(b), or any other payments to You. The Company’s obligation to make the separation payments set forth in this Section 4(b), or any other payments, shall terminate immediately upon any
breach (“Breach”) by You of any post-termination obligations to which You are subject, including, but not limited to, the post-termination obligations set forth in the ECA. Further, if You Breach, the Company shall be entitled to recover
any payments made to You or on Your behalf, including, but not limited to, payments made pursuant to this Section 4(b), and You shall reimburse the Company for all reasonable attorneys’ fees and costs incurred by the Company arising out of
any such Breach. The remedies set forth above shall be in addition to any other legal or equitable remedy the Company may have, but shall not apply to any challenge to the validity of the waiver and release of Your rights under the Age
Discrimination in Employment Act (the “ADEA Waiver”), if applicable. The Company’s right to recover attorneys’ fees and costs in connection with an ADEA Waiver, if applicable, shall be governed by the provisions of the ADEA. 

  
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 4) GENERAL PROVISIONS. 

 

	 	a)	This Agreement constitutes the entire agreement between the Parties concerning the subject matter of this Agreement. This Agreement supersedes any prior communications, agreements or understandings, whether oral or
written, between the Parties relating to the subject matter of this Agreement, including, but not limited to, the Company’s offer letter to You dated December 6, 2011. 

 

	 	b)	This Agreement and the rights and obligations hereunder shall be governed by and construed in accordance with the laws of the State of Wisconsin. The Parties agree that any and all disputes related to or involving this
Agreement shall be litigated in a state or federal court of competent jurisdiction in the city of Waukesha, Wisconsin. The Parties waive (a) any objection to jurisdiction or venue, or (b) any defense claiming lack of jurisdiction or
improper venue, in any action brought in such courts. 

  

	 	c)	In the event of litigation relating to this Agreement, the Company shall, if it is the prevailing party, be entitled to recover attorneys’ fees and costs of litigation in addition to all other remedies available at
law or in equity. 

  

	 	d)	The provisions of this Agreement are severable. If any provision is determined to be invalid, illegal, or unenforceable, in whole or in part, the remaining provisions and any partially enforceable provisions shall
remain in full force and effect. 

  

	 	e)	This Agreement will be assignable to, and will inure to the benefit of, the Company’s successors and assigns, including, without limitation, successors through merger, name change, consolidation, or sale of a
majority of the Company’s stock or assets, and will be binding upon You and Your heirs and assigns. 

  

	 	f)	If You have any outstanding obligations to the Company upon and/or following the termination of this Agreement for any reason, You hereby authorize the Company to deduct any amounts that You owe to the Company from:
(i) Your final paycheck, and/or (ii) any amounts that would otherwise be due to You, including, but not limited to, under Section 3(b) above, except to the extent that any such amounts constitute deferred compensation subject to Code
§409A. 

  

	 	g)	This Agreement shall be interpreted and administered in a manner so that any amount or benefit payable hereunder shall be paid or provided in a manner that is either exempt from or compliant with the requirements of
Code §409A and applicable Internal Revenue Service guidance and Treasury Regulations issued thereunder (and any applicable transition relief under Code §409A). 

Nevertheless, the tax treatment of the benefits provided under the Agreement is not warranted or guaranteed. Neither the Company nor its
directors, officers, employees, or advisers shall be held liable for any taxes, interest, penalties, or other monetary amounts owed by the You as a result of the application of Code §409A. Any right to a series of installment payments under
this Agreement shall, for purposes of Code §409A, be treated as a right to a series of separate payments. 
 5) AFFIRMATION. You
acknowledge that You have carefully read this Agreement, You know and understand its terms and conditions, and You have had the opportunity to ask the Company any questions You may have had prior to signing this Agreement. You acknowledge that the
Company encouraged You to consult with an attorney or other advisor of Your choice regarding the terms of this Agreement, and You have either done so or intentionally chosen no to do so. 

  
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 IN WITNESS WHEREOF, the Parties hereto have executed this Agreement, to be effective as of the
Effective Date. 
  

									
	CONNECTURE, INC.	 		 	DOUGLAS SCHNEIDER
				
	By:	 	 /s/ David A. Jones, Jr.
	 		 	 /s/ Robert Douglas Schneider

					
	Title:	 	Chairman, Board of Directors	 		 	Date:	 	 December 30, 2011

				
	Date:	 	December 15, 2011	 		 	Executed by Employee in Waukesha, Wisconsin.

  
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 AMENDMENT NO. 1 

TO 
 SEPARATION PAY
AGREEMENT 
 This Amendment No. 1 to Separation Pay Agreement (this “Amendment”), dated as of
August 1, 2014 (the “Effective Date”), is by and between Connecture, Inc., a Delaware corporation (the “Company”), and Robert Douglas Schneider (the “Executive”). 

WHEREAS, the Executive and the Company are parties to a Separation Pay Agreement dated and effective as of December 31, 2011 (the
“Separation Agreement”); and 
 WHEREAS, the Executive and the Company now wish to amend the Separation Agreement to
modify the “good reason” definition and increase the severance period from 9 to 12 months. 
 NOW, THEREFORE, the parties hereto
hereby agree as follows effective as of the Effective Date: 
 1. Section 2(g) of the Separation Agreement is amended and restated to
read as follows: 
 Good Reason. Good Reason means Your resignation if: (i) the Company, without Your written
consent, (a) materially reduces Your then current authority, duties or responsibilities or changes your job title and You resign within three hundred sixty-five (365) days of the date on which such action first occurs, (b) materially
reduces Your then current base salary, unless substantially all other executive management employees’ base salary is similarly or proportionately reduced, or (c) materially changes the geographic location at which You must perform services
for the Company; and (ii) in the case of subsections 2(g)(i)(b) and (c), (1) You provide written notice to the Company of any such action within sixty (60) days of the date on which such action first occurs and provide the Company
with thirty (30) days to remedy such action (the “Cure Period”); (2) the Company fails to remedy such action within the Cure Period, and (3) You resign within ten (10) days of the expiration of the Cure Period. Good
Reason shall not include any isolated, insubstantial, or inadvertent action that (a) is not taken in bad faith, and (b) with respect to subsections 2(g)(i)(b) and (c) is remedied by the Company within the Cure Period. 

2. Section 3(b) of the Separation Agreement is amended and restated to read as follows: 

If this Agreement terminates as described in Section 2(f) or Section 2(g) above, then the Company shall pay to You
all accrued but unpaid wages through the termination date based on Your then current base salary. In addition, after Your “separation from service” (as defined in Code section 409A(a)(2)(A)(i)) from the Company, the Company shall
(i) pay You an amount equal to twelve (12) months of Your then current annual base salary, to be paid over a period of twelve (12) months on the first day of each month, in equal installments (each a “Salary Installment”),
beginning on the first day of the next month immediately following the expiration of the 60-Day Release Period (defined below), and (ii) reimburse Your and Your eligible dependents’ actual Consolidated Omnibus Budget Reconciliation Act
(“COBRA”) premium under the Company’s major medical group health plan on a monthly basis for a period of twelve (12) months. If the first day of the month falls on a weekday or a legal holiday, the respective Salary Installment
will be paid on the business day immediately preceding such day. Except as provided in the previous sentence, under no circumstances may any Salary Installment to be made under this Section 3(b) be accelerated or deferred unless agreed to in
writing by the Company and You. 

 3. Section 4(g) of the Separation Agreement is amended to add the following additional
paragraph thereto: 
 If a payment obligation under this Agreement or other compensation arrangement arises on account of
Your separation from service while You are a “specified employee” (as defined under Section 409A and the Treasury Regulations thereunder), any payment of “deferred compensation” (as defined under Treasury Regulation
Section 1.409A-1(b)(1), after giving effect to the exemptions in Treasury Regulation Sections 1.409A-1(b)(3) through (b)(12)) that is scheduled to be paid within six (6) months after such separation from service shall accrue without
interest and shall be paid within 15 days after the end of the six-month period beginning on the date of such separation from service or, if earlier, within 15 days after the appointment of the personal representative or executor of Your estate
following Your death. 
 IN WITNESS WHEREOF, the parties hereto have caused this Amendment to be duly executed as of the Effective Date.

  

					
	CONNECTURE, INC.
		
	By:	 	 /s/ James Purko

		 	Name:	 	James Purko
		 	Title:	 	CFO
	
	Executive:
	
	 /s/ Robert Douglas Schneider

	Robert Douglas Schneider

  
 - 2 -EX-10.11.1

 Exhibit 10.11.1 

Connecture, Inc. 
 18500 W.
Corporate Drive 
 Suite 250 

Brookfield, WI 53045 

December 31, 2013 
 Mr. Dave Sockel

 1235 Zimmer Drive 
 Atlanta, GA 30306 

 

	Re:	Bonus Agreement 

 Dear Dave: 

In consideration for your work for Connecture, Inc., a Delaware corporation (the “Company”), the Company will pay
you a Bonus (as described below) upon the earliest Payment Event (as defined below) to occur after the date of this letter (the “Agreement”), subject to the conditions described herein, so long as you are continuously
employed by the Company (or any controlled affiliate) or its successor from the date of this Agreement through the Payment Event. If your continuous employment with the Company (or any controlled affiliate) and its successor terminates for any
reason before the Payment Event, you will forfeit any and all rights to the Bonus. 
 Subject to the terms of this Agreement, the Bonus will
be paid to you upon the earliest to occur of the following payment events (“Payment Event”): (i) on or within 20 days after the closing of the first public offering of capital stock of the Company that is effected
pursuant to a registration statement filed with, and declared effective by, the Securities and Exchange Commission under the Securities Act of 1933, as amended (“IPO”); provided, however if either the Company or the
Company’s underwriters determine that payment of the Bonus on or within 20 days after the IPO may jeopardize the success of the IPO or subject the Company to other adverse consequences, the Bonus related to an IPO will be paid on
October 1, 2014; (ii) on the closing of a Change of Control (“Change of Control”), as defined in the Connecture, Inc. 2010 Stock Incentive Plan, as may be amended from time to time (the
“Plan”); (iii) on or within 20 days after the closing of an equity financing that results in gross proceeds to the Company of at least $20,000,000 (“Financing”); or (iv) October 1, 2014. 

The amount of the Bonus will depend on which Payment Event triggers the right to payment as follows: 

 

															
	IPO	 	 	Change of Control	 	 	Financing	 	 	October 1, 2014	 
	$	300,000	  	 	$	250,000	  	 	$	250,000	  	 	$	250,000	  

 The Company will pay the Bonus to you in a single lump sum; provided, however, that if net sale proceeds
payable upon a Change of Control are contingent, deferred, or conditional (i.e., escrowed or subject to any earn-out or similar arrangement), then a corresponding portion of the Bonus will be paid to you on the earlier of (x) the date on which
such deferred portion is paid so long as you are continuously employed by the Company (or any controlled affiliate) or its successor from the date of this Agreement through such date, or (y) the date your employment is terminated by the Company
(or any controlled affiliate) or its successor without Cause (as defined in the Plan). For purposes of this Agreement, an asset sale transaction will not be considered a termination of your employment if you are employed by the successor. 

 Notwithstanding anything to the contrary in this Agreement, if the Payment Event is
October 1, 2014, the Company’s obligation to make any Bonus payment will be suspended to the extent and for so long as (x) the making of such Bonus payment would result in a violation or a breach of any covenant contained in any loan
or other bona fide agreement to which the Company or any of its subsidiaries is a party or (y) the Company and its subsidiaries do not have a sufficient amount of cash to support the working capital needs of its business, as determined by the
Company’s board of directors in its sole discretion, and, in each case, subject to Section 409A of the Code and the Treasury Regulations thereunder; provided, however, that, with respect to any suspended Bonus payment, if at any time after
such suspension the conditions in clause (x) and (y) above are both no longer present, then the Company shall make such Bonus payment within 5 business days thereafter. 

The Bonus may be paid in cash or in kind, or in some combination thereof, as determined by the Company in its sole discretion. 

All payments under this Agreement will be subject to all applicable tax withholdings. Notwithstanding anything in this Agreement to the
contrary, in the event that any portion of any payment to you under this Agreement or otherwise may become subject to the excise tax under Section 4999 of the Internal Revenue Code (the “Code”) or may be nondeductible to
the Company (or any affiliate) or its successor under Section 280G of the Code, payment of those amounts shall be contingent upon the Company obtaining the approval of Company stockholders as provided in Section 280G of the Code and the
Treasury Regulations thereunder, and the Company is under no obligation to seek such approval. If such stockholder approval is not obtained, then the portion of the payment under this Agreement that would otherwise cause any amount to be
nondeductible to the Company or its successor under Section 280G of the Code shall be forfeited and you will have no further claim of right to such amount. 

This Agreement contains the entire understanding of the Company and you with respect to the subject matter hereof and supersedes any and all
prior understandings, written or oral. This Agreement may be amended or otherwise modified only by a written instrument signed by both the Company and you. This Agreement and the rights hereunder will be governed by and construed in all respects in
accordance with the laws of the State of Delaware, without regard to its conflict of laws rules. You are not permitted to assign this Agreement or any of your rights hereunder to any other party. 

You acknowledge that you are an employee “at-will” and the Company may terminate your employment at any time for any reason, with or
without cause. You agree that you will sign a release of claims in favor of the Company and its affiliates no later than the date of the first scheduled payment of the Bonus, and no Bonus will be paid if you do not sign the release by that date.
Upon payment of the Bonus, or any earlier dissolution or wind-down of the Company, this Agreement will be cancelled and of no further effect. 

The payments under this Agreement are intended to be exempt from application of Section 409A of the Code. The Company does not guarantee
any particular tax treatment of the compensation arrangement in this Agreement. 
 This Agreement may be executed in counterparts which
together shall be deemed to constitute one instrument. 

  
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 Please acknowledge your agreement to the foregoing by countersigning this Agreement in the space
provided below. 
  

			
	Connecture, Inc.
		
	By:	 	 /s/ Robert Douglas Schneider

	Name:	 	Doug Schneider
	Title:	 	CEO

  

	
	Acknowledged and agreed:
	
	 /s/ Dave Sockel

	Dave Sockel

 [Signature Page to Bonus Agreement] 

  
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