KINGSWAY FINANCIAL SERVICES INC
For the period ended May 18, 2026. Filed Apr 6, 2026.
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What shareholders are asked to vote on at a company's meeting. It is where to find what directors and top executives are paid, and who owns the most shares.
May 18, 2026 · Filed Apr 6, 2026
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UNITED STATES
SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549
SCHEDULE 14A
Proxy Statement Pursuant to Section 14(a) of
The Securities Exchange Act of 1934 (Amendment No. )
Filed by the Registrant☒
Filed by a Party other than the Registrant☐
Check the appropriate box:
| ☐ | Preliminary Proxy Statement |
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| ☐ | Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) |
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| ☒ | Definitive Proxy Statement |
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| ☐ | Definitive Additional Materials |
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| ☐ | Soliciting Material Pursuant to §240.14a-12 |
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KINGSWAY FINANCIAL SERVICES INC.
(Name of Registrant as Specified in Its Charter)
(Name of Person(s) Filing Proxy Statement, if other than the Registrant)
Payment of Filing Fee (Check the appropriate box):
| ☒ | No fee required. |
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| ☐ | Fee paid previously with preliminary materials. |
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| ☐ | Fee computed on table in exhibit required by Item 25(b) per Exchange Act Rules 14a-6(i)(1) and 0-11. |
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NOTICE OF ANNUAL MEETING OF SHAREHOLDERS OF
KINGSWAY FINANCIAL SERVICES INC.
PROXY STATEMENT
FOR THE MEETING TO BE HELD ON MONDAY, MAY 18, 2026
DATED APRIL 6, 2026
NOTICE OF ANNUAL MEETING OF SHAREHOLDERS
NOTICE IS HEREBY GIVEN THAT an annual meeting (the “Meeting”) of the shareholders of Kingsway Financial Services Inc. (the “Corporation”) will be held at 9:00 a.m. Eastern Time (“ET”) on Monday, May 18, 2026. The Meeting will be held in person at the New York Stock Exchange. The purpose of the Meeting is:
| 1) | To elect eight (8) directors of the Corporation to hold office for a term of one (1) year or until their successors are duly appointed and qualified; |
| 2) | To ratify the appointment of Plante & Moran, PLLC as the auditors of the Corporation for the fiscal year ending December 31, 2026; |
| 3) | To approve an amendment to the Corporation’s Certificate of Incorporation to change the Corporate name; |
| 4) | To approve an amendment to the Corporation’s 2020 Equity Incentive Plan dated September 21, 2020 (the “2020 Equity Incentive Plan”) to increase the number of Common Shares reserved for issuance; and |
| 5) | To approve, on a non-binding and advisory basis, the compensation of the named executive officers of the Corporation (say-on-pay) for fiscal year 2025. |
We may also transact such other business as may properly come before the Meeting and any postponements or adjournments thereof.
The accompanying proxy statement provides additional information relating to the matters to be dealt with at the Meeting and is deemed to form part of this Notice of Annual Meeting of Shareholders (the “Notice of Meeting”).
Only shareholders of record at the close of business on March 20, 2026, are entitled to notice of the Meeting and to vote at the Meeting or any adjournment or postponement thereof.
SHAREHOLDERS WHO ARE UNABLE TO ATTEND THE MEETING SHOULD COMPLETE, DATE AND SIGN THE ENCLOSED FORM OF PROXY AND RETURN IT IN THE ENVELOPE PROVIDED FOR THAT PURPOSE, OR VOTE BY TELEPHONE OR OVER THE INTERNET.
Proxies to be used at the Meeting must be deposited with Computershare Investor Services Inc., PO Box 43006, Providence RI 02940-3006 , before 9:00 a.m. ET on May 18, 2026, or if the Meeting is adjourned or postponed, no later than 3:00 p.m. ET on the second business day preceding the day to which the Meeting is adjourned or postponed. The proxy voting cut-off may be waived or extended by the Chairman of the Board at his discretion without notice.
By Order of the Board of Directors
Adam J. Patinkin
Chairman of the Board of Directors
10 S. Riverside Plaza, Suite 1520
Chicago, Illinois 60606
IMPORTANT NOTICE REGARDING THE INTERNET AVAILABILITY OF PROXY MATERIALS FOR THE MEETING OF SHAREHOLDERS TO BE HELD ON MAY 18, 2026.
The proxy statement and our 2025 Annual Report on Form 10-K, including all amendments thereto, are available on our website,www.kingsway-financial.com.
TABLE OF CONTENTS
| LETTER TO SHAREHOLDERS | 1 |
|---|---|
| GENERAL PROXY INFORMATION | 2 |
| Solicitation of Proxies | 2 |
| Quorum | 2 |
| Voting Securities and Principal Holders Thereof | 2 |
| Security Ownership of Certain Beneficial Owners and Management | 3 |
| Delinquent Section 16(a) Reports | 6 |
| Q&A on Proxy Voting | 6 |
| PARTICULARS OF MATTERS TO BE ACTED UPON | 10 |
| Proposal 1 – Election of Directors | 10 |
| Proposal 2 – Appointment of Auditors | 14 |
| Proposal 3 – Amendment to Certificate of Incorporation to Change Corporate Name | 16 |
| Proposal 4 – Amendment to the 2020 Equity Incentive Plan | 17 |
| Proposal 5 – Advisory Vote to Approve Named Executive Officer Compensation | 20 |
| CORPORATE GOVERNANCE MATTERS | 21 |
| Corporate Governance Guidelines and Code of Business Conduct & Ethics | 21 |
| Securities Trading Policy | 21 |
| Board Committees | 21 |
| Communications with the Board | 24 |
| Board Leadership Structure and Role in Risk Oversight | 24 |
| COMPENSATION OF EXECUTIVE OFFICERS AND DIRECTORS | 25 |
| Named Executive Officers for 2025 | 24 |
| 2025 Summary Compensation Table | 25 |
| 2025 Outstanding Equity Awards at Fiscal Year-End | 26 |
| Potential Payments Upon Termination or Change in Control | 26 |
| Policies and Practices for Granting Equity Awards | 26 |
| 2025 Pay Versus Performance Table | 27 |
| Director Compensation | 27 |
| Equity Compensation Plan Information | 28 |
| CERTAIN RELATIONSHIPS AND TRANSACTIONS WITH RELATED PERSONS | 29 |
| OTHER MATTERS | 29 |
| HOUSEHOLDING OF PROXY MATERIALS | 29 |
| SHAREHOLDER PROPOSALS FOR 2026 ANNUAL MEETING | 30 |
| ADDITIONAL INFORMATION | 31 |
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