John T. Fitzgerald
About John T. Fitzgerald
John T. “JT” Fitzgerald, age 53, is President & CEO of Kingsway Financial Services (KFS) and a director since April 21, 2016; he became CEO in September 2018 after serving as EVP from April 2016 and President & COO from March 8, 2017 . He holds a B.S. from DePaul University and an MBA from Northwestern University’s Kellogg School; prior roles include managing director at Adirondack Capital, a seat-owner on the Chicago Board of Trade, and CEO/Chairman of Hunter MFG, LLP (Chairman 2006–2016) . Performance context: company pay-versus-performance disclosures show total shareholder return for a $100 investment at $168.72 (2022), $178.72 (2023), and $154.38 (2024), while net income moved from $15,065k (2022) to $24,012k (2023) and -$8,295k (2024) . Management commentary highlights scaling of the Kingsway Search Xcelerator segment and momentum entering 2025 .
Past Roles
| Organization | Role | Years | Strategic Impact |
|---|---|---|---|
| Kingsway Financial Services | EVP; then President & COO; then CEO | EVP Apr 21, 2016; President & COO Mar 8, 2017; CEO Sep 2018 | Led transition to Search Xcelerator strategy and portfolio scaling |
| Argo Management Group | Co‑founder (private equity investment partnership) | Since 2002 (prior to Kingsway acquisition in 2016) | Provided investment sourcing/management; Argo’s Fund generated distributions to KFS and Fitzgerald in 2023–2024 |
| Hunter MFG, LLP | CEO; Chairman | Chairman 2006–2016 | Operating leadership; experience in building consumer brands |
| Adirondack Capital, LLC | Managing Director | Not disclosed | Financial futures/derivatives trading leadership |
| Chicago Board of Trade | Seat owner | Not disclosed | Market expertise; derivatives trading |
External Roles
No current public company board service disclosed for Fitzgerald; he serves as a KFS director and is not independent .
Fixed Compensation
| Year | Base Salary ($) | Target Bonus % | Actual Bonus ($) | All Other Compensation ($) | Total ($) |
|---|---|---|---|---|---|
| 2024 | 600,000 | Not disclosed | Not yet determined | 37,250 | 637,250 |
| 2023 | 574,231 | Not disclosed | — | 35,961 | 610,192 |
| 2022 | 500,000 | Not disclosed | 500,000 | 32,250 | 1,032,250 |
Notes:
- All Other Compensation includes employer contributions to 401(k) and Employee Share Purchase Plan .
Performance Compensation
Equity Awards and Vesting
| Award Type | Grant Date | Quantity | Vesting Schedule | Status as of 12/31/2024 | Market Value (12/31/2024) |
|---|---|---|---|---|---|
| Restricted Common Shares (2018) | Sep 5, 2018 | 500,000 | Fully vested on Mar 28, 2024; non‑voting until vesting | Fully vested | N/A |
| Restricted Common Shares (2021) | Mar 31, 2021 | 1,000,000 | 200,000 vested at grant; 800,000 vest in 100,000‑share tranches each Sep 5 until 2028 | 400,000 unvested at 12/31/2024 | $3,348,000 at $8.37/share |
| Stock Options | — | — | — | None outstanding | — |
Key terms:
- During restriction periods, dividends/distributions on restricted shares are held by the company and subject to the same vesting restrictions; voting rights exist for the 2021 restricted shares .
- Upcoming tranche overhang: 100,000 shares vest annually on Sep 5 in 2025, 2026, 2027, and 2028 .
Annual Incentive Metrics
| Metric | Weighting | Target | Actual | Payout |
|---|---|---|---|---|
| Profitability (e.g., net income/EBITDA) | Not disclosed | Not disclosed | Considered by Compensation Committee | Not disclosed |
| Shareholder return (TSR) | Not disclosed | Not disclosed | Considered by Compensation Committee | Not disclosed |
| Strategic objectives | Not disclosed | Not disclosed | Considered by Compensation Committee | Not disclosed |
Equity Ownership & Alignment
| Beneficial Ownership | Shares | % Outstanding | Notes |
|---|---|---|---|
| Total beneficial ownership (incl. restricted) | 1,609,529 | 5.84% | Includes 60,000 common shares held indirectly by a trust and 8,000 Class B preferred shares held indirectly; and 400,000 2021 restricted shares |
| Vested vs. unvested | 2018 RSUs fully vested; 2021 RSUs 400,000 unvested at YE 2024 | — | See vesting table above |
| Options (exercisable/unexercisable) | — | — | No option awards outstanding |
| Hedging/Pledging | Hedging and monetization transactions prohibited by KFS policy; no pledging disclosed for Fitzgerald |
Employment Terms
| Term | Detail |
|---|---|
| Role start dates | EVP Apr 21, 2016; President & COO Mar 8, 2017; CEO Sep 2018 |
| Severance (CEO) | Lump‑sum equal to 12 months base salary upon termination without Cause or resignation due to Constructive Termination; requires release |
| Constructive Termination triggers | Material diminution in duties; >10% salary reduction across execs; material reduction in incentive opportunities; hostile work environment (with cure periods) |
| Change‑of‑Control terms | Not disclosed (no CoC multiple or acceleration specified in proxy) |
| Non‑compete / non‑solicit / garden leave | Not disclosed |
Board Governance
- Director since April 21, 2016; not independent; no committee memberships beyond full Board .
- Independent, non‑executive Chairman of the Board (Terence M. Kavanagh) since Sept 16, 2013; board met 8 times in 2024, with ≥75% attendance for each director; independent committees (Audit, Compensation, Nominating, Investment) .
- Compensation Committee members (as of Apr 9, 2025): Joseph D. Stilwell (Chair), Terence M. Kavanagh; the committee has never engaged a compensation consultant .
- Dual‑role implications: CEO also serves as a director, but governance mitigants include independent Chair and fully independent key committees .
Director Compensation (context)
Non‑employee directors receive $80,000 annual cash retainer; Chairman of the Board and Audit Chair each receive an additional $40,000; employee directors like Fitzgerald do not receive director fees .
Related Party Transactions
Argo Holdings Fund I: in 2024, KFS received $1,086,956 in distributions; Fitzgerald received $271,739; two immediate family members each received $135,869 . In 2023, KFS received $456,521; Fitzgerald received $114,130; two immediate family members each received $57,065 .
Performance & Track Record
- TSR and net income trend: $100 TSR value was $168.72 (2022), $178.72 (2023), and $154.38 (2024); net income $15,065k (2022), $24,012k (2023), and -$8,295k (2024) .
- 2024 pay‑versus‑performance tables show lower “compensation actually paid” versus prior years for the CEO amid 2024 earnings pressure .
- 8‑K/press commentary in 2025 emphasizes scaling of the Search Xcelerator portfolio and a perceived business inflection point .
Financial Performance (context)
| Metric | FY 2020 | FY 2021 | FY 2022 | FY 2023 | FY 2024 |
|---|---|---|---|---|---|
| Revenues ($) | 15,023,000* | 1,442,000* | 2,008,000 | 1,848,000* | 1,594,000 |
| EBITDA ($) | 11,343,000* | 5,762,000* | 6,873,000* | 8,383,000* | 7,045,000* |
Values retrieved from S&P Global. Some values lack document citations and are marked with an asterisk.
Risk Indicators & Red Flags
- Securities trading policy prohibits hedging/monetization transactions; no pledging disclosure for Fitzgerald .
- Late Section 16(a) Form 4: one late filing in 2024 for Fitzgerald (administrative error) .
- Prior involvement in Hunter MFG receivership/bankruptcy (2017–2018) disclosed .
Compensation Structure Analysis
- Increased fixed pay share: CEO base rose to $600,000 in 2024; no CEO stock award disclosed in 2024; 2022 included a $500,000 bonus, suggesting higher guaranteed vs. at‑risk mix in 2024 versus 2022 .
- Equity is heavily RSU‑based (2018 and 2021 grants) with long‑dated, annual vesting to 2028; no options outstanding, reducing leverage/risk profile versus options‑heavy plans .
- Performance goal specifics (weights/targets) not disclosed; committee cites profitability, TSR, and strategic objectives qualitatively .
- No CoC multiples or tax gross‑ups disclosed; Compensation Committee does not use consultants, limiting peer‑driven pay inflation risk .
Say‑on‑Pay & Shareholder Feedback
Say‑on‑pay is proposed annually; no historical approval percentages disclosed in the proxy .
Employment & Contracts (Retention Risk)
- Severance provides 12 months of base salary for termination without Cause or constructive termination, with specific protections around role diminishment and incentive opportunity reductions; no disclosed CoC acceleration, implying moderate retention support without golden parachute multiples .
Investment Implications
- Alignment: Fitzgerald holds 5.84% beneficially with sizable unvested RSUs (400k at YE 2024), creating multi‑year alignment via annual vesting and voting rights on 2021 RSUs, though dividends on unvested shares are restricted until vesting .
- Vesting overhang: 100k shares vest each Sep 5 through 2028; expect periodic vest‑related tax withholdings or potential sales around these dates—watch Form 4s near vesting .
- Governance mitigants to dual role: independent Chair and independent committees provide checks on CEO‑director duality; no director fees paid to employee director .
- Pay structure: 2024 compensation shows higher fixed pay with no disclosed CEO equity grant, while legacy RSUs continue to vest; lack of disclosed quantitative incentive targets limits pay‑for‑performance transparency .
- Related party flows: ongoing distributions from Argo Holdings Fund to KFS and Fitzgerald/family indicate continuing ties; monitor for conflicts per KFS related‑party policy .
- Performance context: 2024 net income loss and TSR decline versus 2023 raise execution risk into 2025 despite management’s Search Xcelerator scaling narrative; monitor subsequent quarterly results and capital deployment .