Richard O’Toole
WEBSTER FINANCIALAbout Richard O’Toole
Richard O’Toole, age 68, has served on Webster’s board since 2022 and is the Lead Independent Director. He is Executive Vice President at The Related Companies, with over 40 years of legal, mergers and acquisitions, real estate, and tax expertise, and previously served as General Counsel at Related (2014–2022) . He is affirmed independent under NYSE standards, and in 2024 all directors standing for re-election attended at least 95% of board and committee meetings; every regular board meeting included an executive session of independent directors, presided over by the Lead Independent Director .
Past Roles
| Organization | Role | Tenure | Committees/Impact |
|---|---|---|---|
| The Related Companies | Executive Vice President | 2008–present | Senior executive leadership; growth through development and management of projects |
| The Related Companies | General Counsel | 2014–2022 | Tax structuring and origination of new business opportunities |
| Paul Hastings LLP | Partner, Tax Department | 2000–2005 | Legal and tax expertise |
| Sterling Bancorp | Director; Chair of Board | Director since 2011; Chair 2017–2022 | Led board at Sterling pre-merger; transitioned to WBS board Jan 31, 2022 |
External Roles
| Organization | Role | Tenure | Committees/Impact |
|---|---|---|---|
| Equinox Holding Inc. (private) | Director | Since 2016 | Compensation Committee |
| Motivate (operator of Citi Bike; private) | Director | Since 2015 | Compensation Committee |
| Ladder Capital Corp (NYSE: LADR) | Director (prior) | 2017–2019 | Public company board experience |
Board Governance
- Board leadership structure: Chairman/CEO (Ciulla) and Lead Independent Director (O’Toole). LID responsibilities include presiding over executive sessions, calling meetings of independent directors, reviewing/approving board agendas, contributing to CEO performance review and succession planning, acting as investor advocate, liaising with regulators, and engaging with major stockholders upon request .
- Independence: The board affirmed all directors other than the CEO are independent; committees (Audit, Risk, Compensation & HR, Nominating & Corporate Governance, Technology) are composed solely of independent directors .
- Attendance and engagement: 2024 board held nine meetings; all directors standing for re-election attended at least 95% of board and committee meetings; every regular meeting included an executive session of independent directors .
Committee Assignments and Activity
| Year | Committee Memberships (O’Toole) | Chair Roles | Meetings (2024) |
|---|---|---|---|
| 2025 | Risk; Nominating & Corporate Governance; Executive | Lead Independent Director | Risk: 6 ; Nominating & Corporate Governance: 5 |
| 2024 | Nominating & Corporate Governance (Chair); Compensation; Executive; Lead Independent Director (effective Feb 1, 2024) | Nominating & Corporate Governance Chair; LID | Nominating & Corporate Governance: 4 |
| 2023 | Nominating & Corporate Governance (Chair); Compensation; Executive | Nominating & Corporate Governance Chair | Nominating & Corporate Governance: 3 |
Fixed Compensation
- Director fee structure (2024): Annual board retainer $95,000; annual equity award $115,000; Lead Independent Director additional retainer $45,000; committee chair retainers: Audit $35,000, Risk $30,000, Compensation & HR $20,000, Nominating & Corporate Governance $20,000, Technology $20,000; committee member retainers: Audit $15,000, Risk $12,500, Compensation & HR $10,000, Nominating & Corporate Governance $10,000, Technology $10,000 .
- Director fee structure (2023): Annual board retainer $90,000; annual equity award $110,000; Lead Independent Director retainer $40,000; committee chair retainers as above; member retainers implemented in 2024 following the annual meeting .
O’Toole – Director Compensation (Actuals)
| Metric | 2023 | 2024 |
|---|---|---|
| Fees (Cash) ($) | $110,000 | $149,375 |
| Stock Awards ($) | $106,192 | $113,804 |
| All Other Compensation ($) | $4,334 | $4,154 |
| Total ($) | $220,526 | $267,333 |
Notes: Webster reimburses reasonable travel expenses for directors; no option awards are issued to non-employee directors; none have options outstanding . Equity awards are restricted stock with one-year vest and two-year post-vest holding period; dividends are paid on unvested shares (reflected in “All Other Compensation”) .
Performance Compensation
- Annual director equity grants are time-based restricted shares, not performance-conditioned; vest after one year with a two-year holding period .
- Shareholder-approved annual cap on non-employee director equity awards: $500,000 grant-date fair value under the amended 2021 Stock Incentive Plan .
Equity Grant Details (O’Toole)
| Grant Date | Shares Granted | Grant-Date Price/Share | Grant-Date Fair Value | Vesting/Holding Terms |
|---|---|---|---|---|
| Apr 24, 2024 | 2,499 | $45.54 | Included in $113,804 total award value | 1-year vest; 2-year holding period post-vest |
Other Directorships & Interlocks
| Company | Type | Role | Overlaps / Potential Interlocks |
|---|---|---|---|
| Ladder Capital Corp (NYSE: LADR) | Public | Director (2017–2019) | Prior public company service; no current disclosed business ties to Webster |
| Equinox Holding Inc. | Private | Director; Compensation Committee | No related party transactions disclosed with Webster |
| Motivate (Citi Bike operator) | Private | Director; Compensation Committee | No related party transactions disclosed with Webster |
Expertise & Qualifications
- Over 40 years in legal, M&A, real estate, and tax; strong corporate governance oversight experience .
- Executive leadership at The Related Companies; board leadership at Sterling (Chair) before its merger with Webster .
- Skills matrix shows O’Toole contributes public company/corporate governance, financial services industry, executive leadership, risk management, strategic planning/M&A, and legal/regulatory expertise .
Equity Ownership
| Item | Detail |
|---|---|
| Beneficial Ownership (as of Apr 1, 2025) | 34,976 shares; <1% of outstanding; none pledged |
| Shares Outstanding (as of Apr 1, 2025) | 168,301,119 |
| Director Stock Ownership Guidelines | 5x annual cash retainer ($475,000 for 2024 and 2025); directors not meeting guideline must hold all long-term incentives until compliant |
| Plan Cap for Non-Employee Directors | $500,000 grant-date fair value per calendar year |
Insider Trades and Holdings Updates
| Filing Date | Transaction Date | Form | Summary | Reported Holdings |
|---|---|---|---|---|
| Apr 25, 2024 | Apr 24, 2024 | Form 4 | Annual restricted stock award of 2,499 shares (grant) | N/A |
| May 22, 2025 | May 21, 2025 | Form 4 | Holdings update; beneficial ownership reported for O’Toole |
Governance Assessment
- Strengths: O’Toole’s role as Lead Independent Director provides robust independent oversight, with clearly defined duties including executive session leadership, agenda review, CEO performance input, investor advocacy, and regulator engagement—supporting board effectiveness and investor confidence . He is independent, maintains high attendance, and serves on risk and governance committees with substantive activity (Risk: 6 meetings; Nominating & Corporate Governance: 5 meetings in 2024) . Director compensation is balanced (cash + time-based equity with post-vest holding), aligned to peer medians and subject to ownership guidelines and an annual cap, limiting pay inflation and encouraging long-term alignment .
- Watch items: As an executive at The Related Companies and director at private firms (Equinox, Motivate), monitor for any lending or services transactions that could trigger related party review; Webster’s policies require arm’s-length terms and Nominating & Corporate Governance Committee oversight of related party transactions, and no O’Toole-related transactions are disclosed in 2024/2025 . No pledging of shares is disclosed; anti-pledging is noted at the company level historically, and the 2025 proxy confirms none of such shares are pledged .
- RED FLAGS: None disclosed regarding related party transactions, attendance shortfalls, option repricing, tax gross-ups, or hedging/pledging; director equity is time-based with mandated holding periods .