Margaret Dillon - Director | WHITE MOUNTAINS INSURANCE GROUP (WTM) Executive Profile & Compensation

About Margaret Dillon

Margaret Dillon, age 65, has served as an independent Class III director of White Mountains Insurance Group since 2021, with committee assignments on the Audit Committee and the Compensation/Nominating & Governance Committee (CNG) . She previously held senior leadership roles at Liberty Mutual, bringing extensive executive, financial, and property & casualty insurance expertise to the board . As of March 31, 2025, she beneficially owned 795 WTM shares; no director owns 1% or more of outstanding shares .

Past Roles

Organization	Role	Tenure	Committees/Impact
Liberty Mutual Insurance Company	EVP & Chief Customer Officer, US Consumer Markets	2014–2017	Customer strategy and operations oversight
Liberty Mutual Insurance Company	SVP & CFO, Personal Lines	2002–2014	Financial leadership across U.S. personal lines
Liberty Mutual Insurance Company	Controller, Personal Markets	1998–2001	Financial controls and reporting
International Paper	Technology and finance roles	1984–1993	Early career in tech/finance functions

External Roles

Organization	Role	Tenure/Committee	Notes
Guidewire Software (Public)	Director	Audit Committee	Board-level oversight in core P&C insurance technology domain

Board Governance

Committee assignments: Audit Committee member; CNG Committee member; not a committee chair (Audit Chair is Peter Carlson; CNG Chair is Philip Gelston) .
Independence: The Board determined Dillon is independent under NYSE standards .
Attendance: In 2024 the Board met 6 times; Audit 8; CNG 5; Finance 4. Each director attended more than 75% of aggregate Board and applicable committee meetings; all directors attended the 2024 Annual General Meeting .
Board structure: Independent Board Chair (Weston Hicks) leads executive sessions of non-management directors .
Shareholder engagement: The Board and management reached out to holders of 72% of outstanding shares in 2024; discussions included compensation and governance topics .

Fixed Compensation

Component	Amount ($)	Detail
Annual cash retainer	$135,000	Non-employee directors standard cash retainer
Audit Committee member retainer	$15,000	Additional cash retainer for Audit Committee members
Total cash (2024)	$150,000	Dillon’s “Fees Paid in Cash” for 2024
Annual equity grant	165 shares	Granted May 23, 2024; valued at $1,718.81 per share = $283,604
Stock awards ($)	$283,604	Dillon’s “Stock Awards” for 2024
Total 2024 director compensation	$433,604	Cash + equity; no options or meeting fees disclosed

Notes:

Additional chair retainers do not apply to Dillon (she is not a chair) .
Program intent: equity increases director ownership; directors also eligible for matching gifts up to $10,000 .

Performance Compensation

Grant Date	Shares Awarded	Type	Fair Value ($)	Source
May 23, 2024	165	Director Share Award	$283,604	165 shares valued at $1,718.81 per share
May 22–23, 2025	150	Director Share Award	—	Form 4 filed 05/23/2025 reflecting 150-share director award

Program features:

WTM grants fully valued common shares to directors; no option awards to directors disclosed; equity is time-based, not tied to performance metrics .

Other Directorships & Interlocks

Company	Role	Committee	Potential Interlock Note
Guidewire Software	Director	Audit Committee	Guidewire supplies software to P&C insurers; WTM owns P&C businesses, but no related-party transactions were reported in 2024

Expertise & Qualifications

Extensive financial and P&C insurance domain expertise from Liberty Mutual CFO and customer leadership roles .
Audit committee experience at Guidewire (public company) .
Brings risk oversight and operational acumen relevant to WTM’s multi-segment insurance and capital solutions portfolio .

Equity Ownership

Holder	Beneficial Ownership (shares)	Economically Owned (shares)	Notes
Margaret Dillon	795	795	As of March 31, 2025; no director owns ≥1% of shares
WTM total shares outstanding	—	—	2,573,726 as of March 31, 2025 (context)

Additional alignment policies:

Director stock ownership guideline: 5x annual cash retainer; robust director and executive officer ownership guidelines highlighted by the Board .
Insider Trading Policy in place; policy filed as Exhibit 19 to the 2024 Form 10-K .

Governance Assessment

Strengths: Independent status; dual committee service (Audit and CNG); strong attendance; equity-based director compensation fostering alignment; Board-level shareholder engagement and independent chair leadership .
Compensation mix: Retainer-based cash plus annual common share grants; no options or per-meeting fees; structure emphasizes ownership without pay-for-performance risks for directors .
Conflicts/related-party review: Audit Committee approves related-party transactions; none required approval in 2024; Dillon is on CNG (overseeing governance, succession, ESG) and Audit (oversight of financial integrity and ESG risk) .
RED FLAGS: None disclosed—no pledging noted; no related-party transactions; director equity grants are standard; continued monitoring warranted given Guidewire’s industry role, though no conflict was reported .

Insider Trades (Director Awards & Filings)

Filing Date	Transaction/Period Date	Transaction Type	Shares Acquired	Shares Disposed	Link
05/23/2025	05/22/2025	Director Share Award	150	0	WTM IR Form 4 SEC EDGAR
05/24/2024	05/23/2024	Director Share Award	165	0	WTM IR Form 4
05/28/2021	05/28/2021	Form 3 (Initial)	—	—	Listed on IR Insider Transactions page (no transaction)

Director compensation program elements (for context and benchmarking):

Non-employee director cash retainer $135,000; Audit Committee member retainer $15,000; Audit Chair $35,000; other committee chairs $25,000; Board Chair additional $100,000; annual equity retainer 165 shares (2024 grant) .
2024 director compensation for Dillon: $150,000 cash; $283,604 stock awards; total $433,604 .