Margaret Dillon
Guidewire SoftwareAbout Margaret Dillon
Margaret Dillon, age 66, has served as an independent director of Guidewire Software, Inc. since September 2019 (tenure ~6 years). She previously held senior leadership roles at Liberty Mutual Insurance Company from December 1993 to September 2017, including Senior Vice President and Chief Financial Officer, Personal Insurance, and Executive Vice President and Chief Customer Officer, U.S. Consumer Markets. She holds a B.S. in Computer Science and an M.S. in Finance from Boston College .
Past Roles
| Organization | Role(s) | Tenure | Committees/Impact |
|---|---|---|---|
| Liberty Mutual Insurance Company | Senior Vice President & CFO, Personal Insurance; Executive Vice President & Chief Customer Officer, U.S. Consumer Markets | Dec 1993 – Sep 2017 | Senior operator at a Fortune 500 P&C insurer; deep financial and customer leadership experience |
External Roles
| Organization | Role | Tenure | Public/Private | Committees/Impact |
|---|---|---|---|---|
| White Mountains Insurance Group | Director | Since May 2021 | Public | Diversified insurance and financial services holding company |
| Hi Marley | Director | Since Feb 2022 | Private | SaaS intelligent communication platform for the insurance industry |
Board Governance
- Independence: With the exception of the CEO, all director nominees are independent under Guidewire’s guidelines and NYSE rules; Audit Committee members are independent and meet Rule 10A requirements .
- Committee assignments and expertise:
- Audit Committee member (FY2025); Audit Committee met nine times in FY2025; all current Audit Committee members qualify as “financial experts” as defined by SEC rules .
- Audit Committee member (FY2024); qualifies as “financial expert”; Audit Committee met eight times in FY2024 .
- Nominating & Corporate Governance Committee Chair (FY2024); NCG met four times in FY2024 .
- Attendance and engagement: The Board held five meetings in FY2025; each current director attended at least 75% of Board and applicable committee meetings .
- Board skills matrix: Dillon self-reports experience in insurance industry, senior leadership, investment, governance/risk/compliance, public company board experience, and financial expertise; years on board 6; age 66 .
Fixed Compensation
| Fiscal Year | Fees Earned or Paid in Cash ($) | Stock Awards ($) | Total ($) |
|---|---|---|---|
| FY2025 | 72,301 | 208,885 | 281,186 |
- Program structure (non-employee directors):
- Annual Board cash retainer: $50,000; Chairman of the Board additional $50,000; Lead Customer Advocate additional $30,000 .
- Committee cash retainers: Audit Chair $30,000 (increased from $25,000 effective Jan 1, 2025), Audit Member $12,500; Compensation Chair $20,000, Member $10,000; NCG Chair $10,000, Member $5,000; Risk Chair $20,000, Member $10,000; Business Opportunities Chair $5,000, Member $2,500 .
- Equity: Initial and annual RSU grants targeted at $225,000; actual grant-date fair value may differ due to 10-trading day trailing average pricing methodology .
- No fringe or other benefits for non-employee directors; total annual director pay capped at $750,000 under the 2020 Stock Plan .
Mix and vesting: Based on disclosed amounts ($208,885 stock awards; $72,301 cash), equity comprises approximately 74% of her FY2025 director compensation; RSUs vest in full on the earlier of one-year anniversary of vesting start or the next annual meeting, and fully vest upon a sale of the Company .
Performance Compensation
| Element | Metric Type | Measurement | Applicability to Director Compensation |
|---|---|---|---|
| RSUs (Non-employee director) | Time-based vesting | Full vesting at one-year anniversary or next annual meeting; accelerated on sale | No performance metrics disclosed for director RSUs |
- No performance-vesting (e.g., revenue, EBITDA, TSR) features are disclosed for non-employee director equity grants; awards are time-based .
Other Directorships & Interlocks
| Company | Overlap with GWRE Ecosystem | Potential Interlock/Conflict Note |
|---|---|---|
| White Mountains Insurance Group (Public) | Guidewire serves P&C insurers broadly; no specific transactions disclosed with White Mountains | No related-party transactions involving Ms. Dillon disclosed by Guidewire |
| Hi Marley (Private) | Insurance-focused SaaS; ecosystem adjacency | No related-party transactions involving Ms. Dillon disclosed by Guidewire |
Expertise & Qualifications
- Fortune 500 P&C insurance operator; CFO and customer leadership roles indicate both financial acumen and market-facing expertise .
- Audit Committee “financial expert” designation; broad governance, risk, and compliance experience .
- Skills matrix: insurance industry, senior leadership, public company board experience, investment, financial skills; years on board 6; age 66 .
Equity Ownership
| Holder | Shares Beneficially Owned (#) | Percent of Class (%) | Unvested RSUs (#) | Ownership Guideline Compliance |
|---|---|---|---|---|
| Margaret Dillon | 15,197 | <1% | 1,211 (as of Jul 31, 2025) | Non-employee directors with ≥3 years of service have satisfied guideline of 5x annual cash retainer; Dillon qualifies based on tenure |
- Beneficial ownership methodology includes RSUs issuable within 60 days when determining individual percentages; company outstanding shares at record date: 85,018,893 .
Governance Assessment
- Board effectiveness: Dillon adds domain depth in P&C insurance and financial oversight; Audit Committee financial expert status enhances disclosure integrity and risk oversight .
- Independence and attendance: Independent director with satisfactory engagement (≥75% meeting attendance); Audit Committee independence and qualifications reduce governance risk .
- Compensation alignment: High equity proportion and strict stock ownership guidelines (5x retainer) drive alignment; RSUs time-based without performance features typical for directors; no perquisites disclosed .
- Conflicts/related parties: Company reports one related-party employment involving another director’s family member; no transactions involving Dillon; Audit Committee reviews related-party transactions and maintains oversight of independence .
- Red flags: No late Section 16 filings disclosed for Dillon in FY2025; company noted late filings for other individuals due to administrative error . No hedging/pledging or say-on-pay concerns related to Dillon disclosed in these materials.
Citations: