Form of 2011 Stock Option Award Agreement



 Exhibit 10.1 
 AFFIRMATIVE INSURANCE HOLDINGS, INC. 
 AMENDED AND RESTATED 2004 STOCK
INCENTIVE PLAN 
 as amended 
 STOCK OPTION AGREEMENT 
 This Stock Option Agreement (the
“Agreement”) is made and entered into as of the date of grant set forth below (the “Date of Grant”) by and between Affirmative Insurance Holdings, Inc., a Delaware corporation (the
“Company”), and the participant named below (the “Participant”). Capitalized terms not defined herein shall have the meaning ascribed to them in the Company’s Amended and Restated 2004 Stock
Incentive Plan, as amended (the “Plan”). 
  

			
	Participant:	  	
		  	  

		
	Address:	  	
		  	  

		
	Total Option Shares:	  	
		  	  

		
	Exercise Price Per Share:	  	
		  	  

		
	Date of Grant:	  	
		  	  

		
	Expiration Date:	  	
		  	  

		
	Vesting Commencement Date:	  	
		  	  

		
	Vesting Schedule:	  	The Option will become vested and exercisable with respect to the Shares (as defined below) in three equal annual installments: (i) one-third (1/3) of the Shares will vest and
become exercisable on the first anniversary of the Vesting Commencement Date, (ii) the second one-third (1/3) of the Shares will vest and become exercisable on the second anniversary of the Vesting Commencement Date and (iii) the remaining one-third
(1/3) of the Shares will vest and become exercisable on the third anniversary of the Vesting Commencement Date.
		
	Type of Stock Option:	  	 ̈ Incentive Stock Option
		
		  	x Nonstatutory Stock Option


  
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 1. Grant of Option. The Company hereby grants to Participant an option (this
“Option”) to purchase the total number of shares of Common Stock of the Company set forth above as Total Option Shares (the “Shares”) at the Exercise Price Per Share set forth above (the
“Exercise Price”), subject to all of the terms and conditions of this Agreement and the Plan. If designated as an Incentive Stock Option above, the Option is intended to qualify as an “incentive stock option” (an
“ISO”) within the meaning of Section 422 of the Internal Revenue Code of 1986, as amended (the “Code”), although the Company makes no representation or guarantee that such Option will qualify as
an ISO. 
 2. Exercise Period; Vesting. 
 2.1. Exercise Period. Unless expired as provided in Section 3 of this Agreement, this Option may be exercised from time to time after the Date of Grant set forth above (the
“Date of Grant”) to the extent the Option has vested in accordance with the vesting schedule in Subsection 2.2. 
 2.2. Vesting. Provided Participant’s employment pursuant to his employment agreement has not terminated prior to such vesting dates, the Option will become vested and exercisable according to
the Vesting Schedule. If application of the vesting percentage causes a fractional share, such share shall be rounded down to the nearest whole share for each vesting period except for the last period in such vesting period, at the end of which last
period this Option shall become exercisable for the full remainder of the Shares. The Shares issued upon exercise of the Option will be subject to the restrictions on transfer set forth in Sections 8 and 9 below. 

3. Expiration. The Option shall expire on the Expiration Date set forth above or earlier as provided in Section 4
below or, if applicable, pursuant to Section 11 of the Plan. 
 4. Termination of Continuous Service. 

4.1. Termination for Any Reason Except Death, Disability or Cause. Unless otherwise provided in an employment agreement the terms
of which have been approved by the Administrator, if Participant’s Continuous Service is terminated for any reason, except death, disability or for Cause, the Option, to the extent (and only to the extent) that it would have been exercisable by
Participant on the date of termination, may be exercised by Participant no later than three (3) months after the date of termination, but in any event no later than the Expiration Date. 

4.2. Termination Because of Death or Disability. If Participant’s Continuous Service is terminated because of death or
disability of Participant, the Option, to the extent that it would have been exercisable by Participant on the date of termination, may be exercised by Participant (or Participant’s legal representative) no later than twelve (12) months
after the date of termination, but in any event no later than the Expiration Date. If permitted by this Agreement, any exercise beyond twelve (12) months after the date of termination when the termination is for Participant’s disability is
deemed to be a Nonstatutory Stock Option (an “NSO”) and not an ISO. 

  
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 4.3. Termination for Cause. If Participant’s Continuous Service is terminated
for Cause, then the Option will expire on the Participant’s date of termination. 
 4.4. No Obligation to Employ.
Nothing in the Plan or this Agreement shall confer on Participant any right to continue in the employ of, or other relationship with, the Company or any Affiliate, or limit in any way the right of the Company or any Affiliate to terminate
Participant’s employment or other relationship at any time, with or without Cause. 
 5. Manner of Exercise.

 5.1. Stock Option Exercise Agreement. To exercise this Option, Participant (or in the case of exercise after
Participant’s death or incapacity, Participant’s executor, administrator, heir or legatee, as the case may be) must deliver to the Company an executed stock option exercise agreement in the form attached hereto as Exhibit A, or in
such other form as may be approved by the Administrator from time to time (the “Exercise Agreement”), which shall set forth, inter alia, (a) Participant’s election to exercise the Option, (b) the
number of Shares being purchased, (c) any restrictions imposed on the Shares and (d) any representations, warranties, and agreements regarding Participant’s investment intent and access to information as may be required by the Company
to comply with applicable securities laws. If someone other than Participant exercises the Option, then such person must submit documentation reasonably acceptable to the Company verifying that such person has the legal right to exercise the Option.

 5.2. Limitations on Exercise. The Option may not be exercised unless such exercise is in compliance with all
applicable federal and state securities laws, as they are in effect on the date of exercise. The Option may not be exercised for fewer than one (1) Share unless it is exercised as to all Shares as to which the Option is then exercisable.

 5.3. Payment. The Exercise Agreement shall be accompanied by full payment of the Exercise Price for the shares being
purchased in cash (by certified check or wire transfer), or where permitted by law and upon written approval by the Administrator: 
 (a) by surrender of shares of the Company’s Common Stock that (i) either (1) have been owned by Participant for more than six (6) months and have been paid for within the meaning of
SEC Rule 144 (and, if such shares were purchased from the Company by use of promissory note, such note has been fully paid with respect to such shares); or (2) were obtained by Participant in the open public market; and (ii) are clear of
all liens, claims, encumbrances or security interests; 
 (b) provided that a Listing Date has occurred: (i) through a
“same day sale” commitment from Participant and a broker-dealer that is a member of the National Association of Securities Dealers (an “NASD Dealer”) whereby Participant irrevocably elects to exercise the Option and
to sell a portion of the Shares so purchased sufficient to pay for the total Exercise Price and whereby the NASD Dealer irrevocably commits upon receipt of such Shares to forward the total Exercise Price directly to the Company, or (ii) through
a “margin” commitment from Participant and an NASD Dealer whereby Participant irrevocably elects to exercise the Option and to pledge the Shares so purchased to the NASD Dealer in a margin account as security for a loan from NASD Dealer in
the amount of the total Exercise Price, and 

  
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whereby the NASD Dealer irrevocably commits upon receipt of such Shares to forward the total Exercise Price directly to the Company; provided, however, a cashless exercise by a
Director or executive officer that involves or may involve a direct or indirect extension of credit or arrangement of an extension of credit by the Company or an Affiliate in violation of Section 402(a) of the Sarbanes-Oxley Act (codified as
Section 13(k) of the Securities Exchange Act of 1934, 15 U.S.C. § 78m(k)) shall be prohibited; 
 (c) by any other
form of legal consideration that may be acceptable to the Administrator; or 
 (d) by any combination of the foregoing.

 5.4. Tax Withholding. Prior to the issuance of the Shares upon exercise of the Option, Participant must pay or provide
for any applicable federal, state and local withholding obligations of the Company. 
 5.5. Issuance of Shares. Provided
that the Exercise Agreement and payment are in form and substance satisfactory to counsel for the Company, the Company shall issue the Shares registered in the name of Participant, Participant’s authorized assignee, or Participant’s legal
representative, and shall deliver certificates representing the Shares with the appropriate legends affixed thereto. 
 6.
Notice of Disqualifying Disposition of ISO Shares. If the Option is an ISO, and if Participant sells or otherwise disposes of any of the Shares acquired pursuant to the ISO on or before the later of (a) the date two (2) years after
the Date of Grant, and (b) the date one (1) year after transfer of such Shares to Participant upon exercise of the Option, Participant shall immediately notify the Company in writing of such disposition. Participant agrees that Participant
may be subject to income tax withholding by the Company on the compensation income recognized by Participant from the early disposition by payment in cash or out of the current wages or other compensation payable to Participant. 

7. Compliance with Laws and Regulations. The exercise of the Option and the issuance and transfer of Shares shall be subject to
compliance by the Company and Participant with all applicable requirements of federal and state securities laws and with all applicable requirements of any stock exchange on which the Company’s Common Stock may be listed at the time of such
issuance or transfer. Participant understands that the Company is under no obligation to register or qualify the Shares with the SEC, any state securities commission or any stock exchange to effect such compliance. 

8. Nontransferability of Option. If the Option is an ISO, the Option may not be transferred in any manner other than by will or by
the laws of descent and distribution and may be exercised during the lifetime of Participant only by Participant or in the event of Participant’s incapacity, by Participant’s legal representative. The terms of the Option shall be binding
upon the executors, administrators, successors and assigns of Participant. If the Option is not an ISO, upon written approval by the Administrator, it may be transferred by gift or domestic relations order to a member of the Participant’s
immediate family (child, stepchild, grandchild, parent, stepparent, grandparent, spouse, former spouse, sibling, niece, nephew, mother-in-law, father-in-

  
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law, son-in-law, daughter-in-law, brother-in-law, or sister-in-law, including adoptive relationships, any person sharing the Participant’s household (other than a tenant or employee), a
trust in which these persons have more than 75% of the beneficial interest, a foundation in which these persons (or the Participant) control the management of assets, and any other entity in which these persons (or the Participant) own more than 75%
of the voting interests. 
 9. Privileges of Stock Ownership. Participant shall not have any of the rights of a
stockholder with respect to any Shares until the Shares are issued to Participant. 
 10. General. 

10.1. Interpretation. Any dispute regarding the interpretation of this Agreement shall be submitted by Participant or the Company
to the Administrator for review. The resolution of such a dispute by the Administrator shall be final and binding on the Company and Participant. 
 10.2. Entire Agreement. The Plan and Participant’s employment agreement are incorporated herein by reference. This Agreement and the Plan constitute the entire agreement of the parties and
supercede all prior undertakings and agreements with respect to the subject matter hereof. If any inconsistency should exit between the nondiscretionary terms and conditions of this Agreement and the Plan, the Plan shall govern and control.

 10.3. Notices. Any notice required to be given or delivered to the Company under the terms of this Agreement shall be
in writing and addressed to the Corporate Secretary of the Company at its principal corporate offices. Any notice required to be given or delivered to Participant shall be in writing and addressed to Participant at the address indicated above or to
such other address as such party may designate in writing from time to time to the Company. All notices shall be deemed to have been given or delivered upon: (a) personal delivery; (b) five (5) days after deposit in the United States
mail by certified or registered mail (return receipt requested); (c) two (2) business day after deposit with any return receipt express courier (prepaid); or (d) one (1) business day after transmission by facsimile. 

10.4. Successors and Assigns. The Company may assign any of its rights under this Agreement. This Agreement shall be binding upon
and inure to the benefit of the successors and assigns of the Company. Subject to the restrictions on transfer set forth herein, this Agreement shall be binding upon Participant and Participant’s heirs, executors, administrators, legal
representatives, successors and assigns. 
 10.5. Governing Law. This Agreement shall be governed by and construed in
accordance with the laws of the State of Delaware without giving effect to its conflict of law principles. If any provision of this Agreement is determined by a court of law to be illegal or unenforceable, then such provision will be enforced to the
maximum extent possible and the other provisions will remain fully effective and enforceable. 
 11. Acceptance.
Participant hereby acknowledges receipt of a copy of the Plan and this Agreement. Participant has read and understands the terms and provisions thereof, and accepts the Option subject to all the terms and conditions of the Plan and this Agreement.
Participant acknowledges that there may be adverse tax consequences upon exercise of the Option or disposition of the Shares and that Participant should consult a tax advisor prior to such exercise or disposition. 

[SIGNATURE PAGE FOLLOWS] 

  
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 IN WITNESS WHEREOF, the Company has caused this Agreement to be executed by its duly
authorized representative and Participant has executed this Agreement, effective as of the Date of Grant. 

AFFIRMATIVE INSURANCE HOLDINGS, INC. 

By:                   
                                         
                                         
                                    

Name: Gary Y. Kusumi 
 Title: Chief Executive Officer 
 PARTICIPANT 

 

                   
                                         
                                         
                                         
  
 (Signature) 

Printed Name: 
  

  
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 EXHIBIT A 
 FORM OF STOCK OPTION EXERCISE AGREEMENT 
 AFFIRMATIVE INSURANCE HOLDINGS, INC.

 AMENDED AND RESTATED 2004 STOCK INCENTIVE PLAN 

as amended 

STOCK OPTION EXERCISE AGREEMENT 
 This Stock Option Exercise Agreement (the “Exercise Agreement”) is made and entered into as
of                             (the “Effective Date”), by and between Affirmative
Insurance Holdings, Inc., a Delaware corporation (the “Company”), and the purchaser named below (the “Purchaser”). Capitalized terms not defined herein shall have the meanings ascribed to them in the
Company’s Amended and Restated 2004 Stock Incentive Plan, as amended (the “Plan”) or the Stock Option Agreement. 
  

			
	 Participant:
	    	 
		
	 Social Security Number:
	    	 
		
	 Address:
	    	 
		
		    	 
		
	 Option Shares Being Purchased:
	    	 
		
	 Exercise Price Per Share:
	    	 
		
	 Date of Grant:
	    	 
		
	 Expiration Date:
	    	 
		
	 Type of Stock Option:
	    	 ̈ Incentive Stock Option
		
		    	x Nonstatutory Stock Option

 1. Exercise of Option. 

1.1. Exercise. Pursuant to exercise of that certain option (the “Option”) granted to Purchaser under the
Plan and the Stock Option Agreement and subject to the terms and conditions of this Exercise Agreement, Purchaser hereby purchases from the Company, and the Company hereby sells to Purchaser, the Total Number of Shares set forth above (the
“Shares”) of the Company’s Common Stock at the Exercise Price Per Share set forth above (the “Exercise Price”). As used in this Exercise Agreement, the term “Shares” refers
to the Shares purchased under this Exercise Agreement and includes all securities received (a) in replacement of the Shares, (b) as a result of stock dividends or stock splits with respect to the Shares, and (c) all securities
received in replacement of the Shares in a merger, recapitalization, reorganization or similar corporate transaction. 

  
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 1.2. Title to Shares. The exact spelling of the name(s) under which
Purchaser will take title to the Shares is: 
 Purchaser desires to take title to the Shares as follows: 

 ̈ Individual, as separate property 

 ̈ Husband and wife, as community property 

 ̈ Joint Tenants 
  ̈ Other; please specify: 
 1.3.
Payment. Purchaser hereby delivers payment of the Exercise Price in cash (by check), whether or not acquired through a loan from the Company, in the amount of $            , receipt
of which is acknowledged by the Company. 
 2. Delivery. 

2.1. Deliveries by Purchaser. Purchaser hereby delivers to the Company (a) this Exercise Agreement, (b) if
Purchaser is married, a consent of spouse in the form of Exhibit A attached hereto executed by Purchaser’s spouse, (c) the Exercise Price and payment or other provision for any applicable tax obligations in the form of a check,
or, if permitted under applicable law and permitted by the Administrator, a secured full recourse promissory note (“Note”) and (d) if the Purchaser has provided a Note for exercise of the Shares, a stock pledge agreement
executed by Purchaser (“Pledge Agreement”) and two (2) copies of a blank stock power (“Stock Power”), both executed by Purchaser (and Purchaser’s spouse, if any). 

2.2. Deliveries by the Company. Upon its receipt of the Exercise Price, payment or other provision for any applicable tax
obligations and all the documents to be executed and delivered by Purchaser to the Company under Section 2.1 hereof, the Company will issue a duly executed stock certificate evidencing the Shares in the name of Purchaser,
provided, however, if the Purchaser has provided a Note for exercise of the Shares, such stock certificate shall be placed in escrow as provided in Section 10 hereof to secure payment of Purchaser’s obligation under
the Note. 
 3. Representations and Warranties of Purchaser. Purchaser represents and warrants to the Company that:

 3.1. Agrees to Terms of the Plan. Purchaser has received a copy of the Plan and the Stock Option Agreement, has read
and understands the terms of the Plan, the Stock Option Agreement and this Exercise Agreement, and agrees to be bound by their terms and conditions. Purchaser acknowledges that there may be adverse tax consequences upon exercise of the Option or
disposition of the Shares, and that Purchaser should consult a tax advisor prior to such exercise or disposition. 

  
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 3.2. SEC Rule 144. Purchaser understands that Rule 144 promulgated under the
Securities Act may indefinitely restrict transfer of the Shares so long as Purchaser remains an “affiliate” of the Company or if “current public information” about the Company (as defined in Rule 144) is not publicly available.

 4. Compliance with Securities Laws. Purchaser understands and acknowledges that, notwithstanding any
other provision of the Stock Option Agreement to the contrary, the exercise of any rights to purchase any Shares is expressly conditioned upon compliance with the Securities Act and all applicable state securities laws. Purchaser agrees to cooperate
with the Company to ensure compliance with such laws. 
 5. Rights as a Stockholder. Subject to the terms and conditions
of this Exercise Agreement, Purchaser will have all of the rights of a stockholder of the Company with respect to the Shares from and after the date that Shares are issued to Purchaser until such time as Purchaser disposes of the Shares. 

6. Escrow. If the Purchaser has provided a Note for exercise of the Shares, as security for Purchaser’s faithful performance
of this Exercise Agreement, Purchaser agrees, immediately upon receipt of the stock certificate(s) evidencing the Shares, to deliver such certificate(s), together with the Stock Powers executed by Purchaser and by Purchaser’s spouse, if any
(with the date and number of Shares left blank), to the Secretary of the Company or other designee of the Company (the “Escrow Holder”), who is hereby appointed to hold such certificate(s) and Stock Powers in escrow and
to take all such actions and to effectuate all such transfers and/or releases of such Shares as are in accordance with the terms of this Exercise Agreement. Purchaser and the Company agree that Escrow Holder will not be liable to any party to this
Exercise Agreement (or to any other party) for any actions or omissions unless Escrow Holder is grossly negligent or intentionally fraudulent in carrying out the duties of Escrow Holder under this Exercise Agreement. Escrow Holder may rely upon any
letter, notice or other document executed with any signature purported to be genuine and may rely on the advice of counsel and obey any order of any court with respect to the transactions contemplated by this Exercise Agreement. The Shares will
remain in escrow so long as they are subject to the Pledge Agreement. 
 7. Tax Consequences. PURCHASER UNDERSTANDS THAT
PURCHASER MAY SUFFER ADVERSE TAX CONSEQUENCES AS A RESULT OF PURCHASER’S PURCHASE OR DISPOSITION OF THE SHARES. PURCHASER REPRESENTS: (a) THAT PURCHASER HAS CONSULTED WITH ANY TAX ADVISOR THAT PURCHASER DEEMS ADVISABLE IN CONNECTION WITH
THE PURCHASE OR DISPOSITION OF THE SHARES AND (b) THAT PURCHASER IS NOT RELYING ON THE COMPANY FOR ANY TAX ADVICE. 

  
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 8. Compliance with Laws and Regulations. The issuance and transfer of the Shares will
be subject to and conditioned upon compliance by the Company and Purchaser with all applicable state, local and U.S. Federal laws and regulations and with all applicable requirements of any stock exchange or automated quotation system on which the
Company’s Common Stock may be listed or quoted at the time of such issuance or transfer. 
 9. Successors and
Assigns. The Company may assign any of its rights under this Exercise Agreement. This Exercise Agreement shall be binding upon and inure to the benefit of the successors and assigns of the Company. This exercise Agreement will be binding upon
Purchaser and Purchaser’s heirs, executors, administrators, legal representatives, successors and assigns. 
 10.
Governing Law; Severability. This Exercise Agreement shall be governed by and construed in accordance with the laws of the State of Delaware without giving effect to its conflict of law principles. If any provision of this Exercise Agreement
is determined by a court of law to be illegal or unenforceable, then such provision will be enforced to the maximum extent possible and the other provisions will remain fully effective and enforceable. 

11. Notices. Any notice required to be given or delivered to the Company shall be in writing and addressed to the Corporate
Secretary of the Company at its principal corporate offices. Any notice required to be given or delivered to Purchaser shall be in writing and addressed to Purchaser at the address indicated above or to such other address as Purchaser may designate
in writing from time to time to the Company. All notices shall be deemed effectively given upon personal delivery, (a) five (5) days after deposit in the United States mail by certified or registered mail (return receipt requested),
(b) two (2) business day after its deposit with any return receipt express courier (prepaid), or (c) one (1) business day after transmission by facsimile. 
 12. Further Instruments. The parties agree to execute such further instruments and to take such further action as may be reasonably necessary to carry out the purposes and intent of this Exercise
Agreement. 
 13. Headings. The captions and headings of this Exercise Agreement are included for ease of reference only
and will be disregarded in interpreting or construing this Exercise Agreement. 
 14. Entire Agreement. The Plan, the
Stock Option Agreement and this Exercise Agreement, together with all Exhibits thereto, constitute the entire agreement and understanding of the parties with respect to the subject matter of this Exercise Agreement, and supersede all prior
understandings and agreements, whether oral or written, between the parties hereto with respect to the specific subject matter hereof. If there is any inconsistency between the terms of this Exercise Agreement and the terms of the Plan and Stock
Option Agreement, the terms of the Plan and Stock Option Agreement shall govern and control. 
 [SIGNATURE PAGE FOLLOWS]


  
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 IN WITNESS WHEREOF, the Company has caused this Exercise Agreement to be executed in
triplicate by its duly authorized representative and Purchaser has executed this Exercise Agreement in triplicate as of the Effective Date, indicated above. 

 

			
	AFFIRMATIVE INSURANCE HOLDINGS, INC.
		
	 By:
	 	 
	 Name:
	 	 
	 Title:
	 	 
	
	PARTICIPANT
	
	 
	 (Signature)

	
	 Printed Name:




  
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 EXHIBIT A 
 SPOUSE CONSENT 
 The undersigned spouse of (the
“Purchaser”) has read, understands, and hereby approves the Stock Option Exercise Agreement (the “Agreement”) between Purchaser and Affirmative Insurance Holdings, Inc., a Delaware corporation (the
“Company”). In consideration of the Company’s granting my spouse the right to purchase the Shares as set forth in the Agreement, the undersigned hereby agrees to be irrevocably bound by the Agreement and further agrees
that any community property interest I may have in the Shares shall similarly be bound by the Agreement. The undersigned hereby appoints Purchaser as my attorney-in-fact with respect to any amendment or exercise of any rights under the Agreement.

  

			
	 Dated:
	 	 
	
	SPOUSE
	
	  
 (Signature)

	
	  
 Printed Name

		
	 Address: