Company: OSBC
Filing Date: 2025-05-08
Form Type: 424B3
Source: 0001104659-25-046065
Chunk: 381

Company: OLD SECOND BANCORP INC
Filing Date: 2025-05-08
Form: 424B3
Chunk 381
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 Executive desires to serve on the Boards and continue employment with the Company under the terms and provisions set forth below; and

### WHEREAS
, the Company and the Executive desire to enter into this Agreement to provide certain benefits to the Executive and certain protections for the Bank, subject to and in accordance with this Agreement; and

### WHEREAS
, the Executive acknowledges that the restrictions contained herein are necessary and reasonable in scope and duration and are a material inducement for the Company to enter into this Agreement and the corresponding Compensation and Benefits Assurance Agreement executed contemporaneously herewith (the “

#### CBAA
”) and commence a relationship with the Executive.

#### NOW, THEREFORE
, in consideration of the foregoing recitals and the provisions hereafter set forth, and for other good and valuable consideration, the receipt and sufficiency of which are mutually acknowledged, the parties hereto agree as follows:

1.

#### Employment; Service as a Director.
The Company hereby agrees to employ the Executive from and after the Effective Time as an Executive Vice President and as “President of National Specialty Lending,” “President, FreedomRoad Financial” and “President, Performance Finance” of the Bank and the Company, with such authority, duties and responsibilities as set forth on Exhibit A , reporting to, and subject to the direction of, the Chief Executive Officer of the Company (the “

#### CEO
”). At the Effective Time, Executive shall be appointed to the boards of directors of both the Company and the Bank (the “

#### Boards
”). During the Term, the Company shall also cause the Executive to be nominated to stand for election to the Boards as described in Section 7.12 of the Merger Agreement, and if so elected the Executive shall serve for no additional consideration as a member of those Boards. While employed under this Agreement, the Executive shall at all times devote his full time, attention, and best efforts on behalf of the Company and the Bank, and shall perform all services, acts, and duties connected with his position in such manner as the Company and the Bank from time to time shall direct, acting at all times in good faith and in the Company’s and the Bank’s best interests.

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TABLE OF CONTENTS

2.

#### Term.
The Company agrees to employ the Executive and the Executive agrees to serve as an Executive of the Company for an indefinite period (such period from the Effective Time to the termination of the Executive’s employment is referred to as the “

#### Term