Matthew Winter
H&R BLOCKAbout Matthew E. Winter
Matthew E. Winter (age 68) has served on H&R Block’s Board since 2017 and currently chairs the Compensation Committee while also serving on the Audit Committee . He is a former President of The Allstate Corporation (2015–2018) and previously led Allstate Personal Lines, with earlier senior roles across major financial institutions and insurers; he holds a B.S. (University of Michigan), J.D. (Albany Law School), LL.M. (University of Virginia), and completed Harvard Business School’s Advanced Management Program . The Board has affirmatively determined Winter is independent under NYSE standards and H&R Block’s Independence Standards . He earned the CERT Certificate in Cybersecurity Oversight from Carnegie Mellon University in July 2023, enhancing his risk and cyber governance credentials .
Past Roles
| Organization | Role | Tenure | Committees/Impact |
|---|---|---|---|
| The Allstate Corporation | President | Jan 2015 – Feb 2018 | Led enterprise operations and strategy across personal lines insurance |
| Allstate Insurance Company | President, Allstate Personal Lines | Began Dec 2013 | Drove consumer products and operations execution in personal lines |
| Allstate Corporation/Insurance Company | Various executive roles | 2009 onward (prior to roles above) | Senior leadership across operations/financial services |
| U.S. Army | Active duty | >12 years | Leadership discipline and risk management background |
| Legal Practice | Attorney | Several years | Legal expertise relevant to governance/compliance |
External Roles
| Organization | Role | Tenure | Committees/Impact |
|---|---|---|---|
| ADT Inc. | Lead Independent Director | Current | Board leadership; oversight of governance and strategy |
| The Hartford Financial Services Group, Inc. | Director | Current | Insurance and financial services oversight |
| Winter‑Lehman Family Foundation | Board | Current | Philanthropy governance |
| Stockbridge Bowl Association | Board | Current | Community non-profit governance |
| Volunteers in Medicine – Berkshires | Board of Trustees | Current | Non-profit health services oversight |
| Feeding America; Leukemia & Lymphoma Society; Houston Food Bank; CT/Houston Opera | Former Director | Prior | Non-profit and civic board experience |
Board Governance
- Committee assignments: Compensation Committee Chair; Audit Committee member .
- Audit Committee financial expert: Board determined Winter, Johnson, and Reich each qualify under SEC criteria; all Audit members are independent .
- Independence: Board affirmed Winter (and 6 other directors) are independent under NYSE and company standards .
- Attendance: Board held 6 meetings in FY2025; every incumbent director attended at least 75% of applicable Board/committee meetings; overall attendance exceeded 95% .
- Annual meeting: All current directors virtually attended last year’s annual meeting .
- Board leadership: Independent Chairman structure; Chairman leads executive sessions of non-employee directors at each regular Board meeting .
- ESG and risk oversight: Board and committees maintain ERM, cyber, and ESG oversight; Audit receives at least annual information security deep dives .
Fixed Compensation
| Component | Amount | Notes |
|---|---|---|
| Annual Cash Board Retainer | $85,000 | Paid quarterly |
| Compensation Committee Chair Retainer | $25,000 | Chair fee |
| Audit Committee Member Retainer | $15,000 | Member fee |
| Fees Earned or Paid in Cash (FY2025) | $125,000 | Winter total cash (retainer + chair + member) |
| Annual Equity Retainer (DSUs) | $190,000 | Granted post-election; DSUs fully vested at grant |
| Stock Awards (ASC 718 fair value, FY2025) | $196,813 | Reported grant-date fair value |
| H&R Block Foundation Match | $5,000 | 501(c)(3) match |
| Total Director Compensation (FY2025) | $326,813 | Cash + stock + other |
| Compensation Cap | $750,000 | Annual cap per 2018 Plan (excludes added Chairman-only compensation) |
| Ownership Guidelines (Directors) | 5x annual cash retainer | Retain covered shares until guideline met; prohibits pledging/hedging |
Performance Compensation
| Instrument | Grant Date | Value | Units Outstanding | Vesting/Payment | Dividend Treatment |
|---|---|---|---|---|---|
| DSUs (Annual Director Grant) | Nov 6, 2024 | ≈$190,000 | 54,359 DSUs outstanding as of 6/30/2025 | Fully vested at grant; payable in common stock 6 months after service ends | No dividends prior to payment; dividend equivalents accrue and are paid when DSUs become payable |
| Share Units & Equivalents (beneficial ownership measure) | As of Sept 15, 2025 | N/A | 54,705 | Includes DSUs and other share equivalents; no voting rights | Value mirrors common stock |
Directors do not receive options or performance-conditioned equity; there are no director meeting fees unless meetings exceed 10/year . As of June 30, 2025, no non-employee director had stock options outstanding .
Other Directorships & Interlocks
| Company | Sector | Role | Potential Interlock/Conflict Consideration |
|---|---|---|---|
| ADT Inc. | Security services | Lead Independent Director | No HRB-related party transactions reported in FY2025; Board policy requires G&N review/approval if any arise |
| The Hartford | Insurance/financial services | Director | No related party transactions reported in FY2025; any >$120k transaction would trigger review |
- Director service limit: Governance Guidelines restrict directors to no more than three other public company boards; current nominees comply .
- Related person transactions: Company reported none since start of FY2025 beyond executive compensation items .
Expertise & Qualifications
- Executive leadership and operating experience across insurance and financial services; former President of Allstate .
- Financial literacy and audit committee financial expert designation; robust ERM and cyber governance exposure .
- Cyber oversight credential (CERT Certificate, July 2023) signaling board-level cybersecurity proficiency .
- Public company governance experience and committee leadership (Compensation Chair) .
Equity Ownership
| Holder | Beneficially Owned Shares | Share Units & Equivalents | Total | % of Class |
|---|---|---|---|---|
| Matthew E. Winter | — | 54,705 | 54,705 | <1% (*) |
- Director stock ownership guidelines: minimum holdings equal to 5x annual cash retainer; covered shares include directly/indirectly owned shares, equivalents, and after-tax vested option value (if any) .
- Hedging/pledging: Prohibited by Insider Trading Policy; directors cannot pledge company stock or engage in derivatives/hedging .
Governance Assessment
- Positive signals: Independent status; dual committee roles with Compensation Chair and Audit member; audit committee financial expert; strong attendance; independent Chairman structure with regular executive sessions; robust ERM and cyber oversight; formal related-party policy with G&N review .
- Pay-for-performance governance: High say-on-pay support in 2024 (≈98%), reflecting investor confidence in comp oversight; use of independent compensation consultant (CAP LLC) and defined peer groups for benchmarking .
- Alignment: Director pay mix balances cash retainer with DSUs; ownership guidelines enhance alignment, with prohibitions on hedging/pledging .
- Potential risks/RED FLAGS: None disclosed regarding attendance shortfalls, related-party transactions, pledging, or option repricing; director service counts comply with guidelines .