Exhibit 10.1

EXECUTIVE TRANSITION ADDENDUM

TO

EXECUTIVE EMPLOYMENT AGREEMENT

This Executive Transition Addendum (“Addendum”) is entered into as of this 4th
day of April, 2013 (the “Effective Date”), by and between Gary Y. Kusumi
(“Executive”) and Affirmative Insurance Holdings, Inc. (the “Company”).

WHEREAS, Executive currently serves as Chief Executive Officer (“CEO”) and as
Chairman of the Board of Directors (the “Board”) of the Company;

WHEREAS, Executive and the Company previously entered into that Executive
Employment Agreement dated October 1, 2010 (the “Employment Agreement”);

WHEREAS, the Employment Agreement expires on October 1, 2013 (the “Expiration
Date”) and the Executive has informed the Board that he will retire at the
Expiration Date;

WHEREAS, the Company will appoint an Acting Chief Executive Officer (the “Acting
CEO”) as of the Effective Date;

WHEREAS, the Company and Executive mutually agree that it is in the best
interests of the Company to retain through the Expiration Date Executive’s
advice and counsel on matters related to business operations and any other
matters pertaining to the Company that may assist management and the Board; and

WHEREAS, the Company and Executive desire to enter into this Addendum that
contemplates Executive’s retention until the Expiration Date.

NOW, THEREFORE, in consideration of the mutual promises and covenants contained
herein, it is hereby agreed by and between the parties hereto as follows
effective as of the Effective Date:

1. CONTINUED EMPLOYMENT.

1.1 Term of Employment. Executive’s term of employment under this Addendum shall
begin on the Effective Date and end on the Expiration Date (the “Employment
Term”).

1.2 Transition. As of the Effective Date, employees of the Company then
reporting to Executive shall report to the Acting CEO, and the Acting CEO shall
report to the Board. As reasonably requested by the Board, Executive shall
assist and advise the Acting CEO regarding all matters in which Executive was
involved or of which Executive had knowledge while employed by the Company. The
Board will nominate Executive to become a member of the Board for 2013-2014. For
the avoidance of doubt, Executive expressly agrees that none of the activities
related to the transition of duties described in this Addendum shall constitute
“Good Reason” as defined in the Employment Agreement.

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2. COMPENSATION. For services during the Employment Term, Executive shall
receive through the Expiration Date the compensation and benefits provided
pursuant to the terms and conditions of the Employment Agreement.

3. GENERAL PROVISIONS. Except as otherwise expressly set forth in this Addendum,
the Employment Agreement shall continue in full force and effect.

IN WITNESS WHEREOF, the parties have executed this Addendum as of this 4th day
of April, 2013.

 

Affirmative Insurance Holdings, Inc. By:  

/s/ David I. Schamis

Name:   David I. Schamis Title:   Chairman, Compensation Committee

 

Accepted and agreed:

/s/ Gary Y. Kusumi

Gary Y. Kusumi