Lesley Thompson
About Lesley Thompson
Independent director since 2021; age 52; Managing Director, Willis Towers Watson Management (Cayman) Ltd. since March 2020 and Secretary since April 2020; credentials include ACMA & CGMA, Fellow of Captive Insurance (FCI), and Accredited Director (Acc. Dir.) through the Chartered Governance Institute of Canada . She brings insurance, accounting, and corporate governance experience to the board .
Past Roles
| Organization | Role | Tenure | Committees/Impact |
|---|---|---|---|
| Willis Towers Watson Management (Cayman) Ltd. | Managing Director; Secretary | Mar 2020–present; Apr 2020–present | Leads insurance management and brokerage; governance responsibility |
| Maples Fiduciary Services (Cayman) Ltd. | Vice President | Feb 2016–Mar 2020 | Headed insurance management; provided independent director services |
| Aon Insurance Managers (Bermuda) Ltd.; HSBC Financial Services (Cayman) Ltd.; Atlas Insurance Management (Cayman) Ltd.; Advantage International Management (Cayman) Ltd. | Senior roles (Assistant VP, Assistant Manager, Group VP) | Jan 2000–Jan 2016 | Managed large portfolios of P&C and life & annuity captives/SPVs/segregated portfolios |
External Roles
| Organization | Role | Tenure | Notes |
|---|---|---|---|
| ICP Investment Holdings Limited | Director | Nov 2016–present | External directorship |
| ICP Reinsurance Limited | Director | Jan 2017–present | External directorship |
| Evergreen Pacific Reinsurance Company Limited | Director | Aug 2019–(disclosed as current in 2022 proxy) | Listed in 2022 proxy biography |
| Insurance Managers Association of Cayman | Executive Committee member; past Chairperson | Since Aug 2020 | Industry leadership |
Board Governance
- Independence: Board determined Thompson is independent under Nasdaq and SEC rules; Audit, Compensation, and Nominating committees are fully independent .
- Committee assignments and chair roles:
- Audit Committee member; designated “audit committee financial expert” .
- Compensation Committee member .
- Nominating & Corporate Governance Committee Chair .
- Underwriting Committee Chair .
- Investment Committee: nominee list indicates membership, while the committee roster shows Investment Committee composed of Gowda (Chair), Timothy, Madhu; Thompson is not listed there (note the inconsistency in proxy sections) .
- Attendance: Board held five meetings in 2023; each director attended at least 80% .
- Lead Independent Director: not disclosed.
- Executive sessions frequency: not disclosed.
Fixed Compensation
| Component | Amount | Period | Details |
|---|---|---|---|
| Annual cash retainer | $15,000 | FY2024 | Non-Employee Director Compensation Program |
| Annual cash retainer | $15,000 | FY2023 | Non-Employee Director Compensation Program |
| Meeting/committee fees | Not separately disclosed | — | Board authorized director remuneration; not itemized beyond cash retainer |
Performance Compensation
| Grant Type | Grant Date | Shares/Units | Fair Value | Vesting | Notes |
|---|---|---|---|---|---|
| Restricted ordinary shares (OXBR) | Jan 2, 2024 | 23,809 | $25,000 (aggregate grant date value per director table) | 50% at 180 days; 50% at first anniversary | Granted to each non-employee director under 2021 Plan |
| Restricted ordinary shares (OXBR) | Jan 9, 2024 | 10,549 | $25,000 (aggregate value per 2023 table context) | 50% at 180 days; 50% at first anniversary | Earlier proxy notes this grant; subsequent EGM proxy lists 23,809 shares—company disclosures differ on count |
| Restricted shares (SP Holdings subsidiary) | Mar 25, 2024 | 2,000 | Not disclosed | Vests ratably over 1 year | SurancePlus Holdings 2024 Plan; for non-employee directors including Thompson |
- Equity plan guardrails: 2025 Omnibus Incentive Plan prohibits repricing/backdating; no excise tax gross-ups on change-of-control; clawback policy applies to incentive-based compensation; performance goals include revenue, EBITDA, TSR, margins, underwriting metrics (PML/AAL), ROE, cash flow, etc. .
Other Directorships & Interlocks
| Company | Relationship to OXBR | Potential Interlock/Conflict |
|---|---|---|
| Willis Towers Watson group (WTW) | Global broker/insurance services; Thompson leads WTW Cayman | Potential perceived conflict if WTW provides services to OXBR entities; no related-party transaction disclosed involving Thompson |
| ICP Investment Holdings; ICP Reinsurance; Evergreen Pacific Re | External insurance/reinsurance entities | No disclosed transactions with OXBR; monitor for business overlaps |
Expertise & Qualifications
- Chartered Management Accountant (ACMA & CGMA); Fellow of Captive Insurance (FCI); Accredited Director (Acc. Dir.) .
- Designated audit committee financial expert .
- Deep insurance management, captive governance, underwriting oversight; past leadership in industry association .
Equity Ownership
| As-of Date | Beneficially Owned Shares | % of Outstanding | Notes |
|---|---|---|---|
| Apr 15, 2024 | 50,358 | <1% | As per principal shareholders table |
| Dec 31, 2024 (restricted shares outstanding) | 50,358 | N/A | Aggregate restricted stock awards outstanding |
| Jul 25, 2025 | 56,412 | <1% | Beneficial ownership updated; “less than 1%” indicated |
- Hedging/pledging: Company insider trading policy prohibits hedging in OXBR equity; pledging not specifically addressed in disclosed policy .
- Ownership guidelines: not disclosed for directors .
Governance Assessment
- Committee effectiveness: Thompson chairs Nominating & Corporate Governance and Underwriting Committees; is Audit and Compensation member; designated financial expert, supporting board oversight of financial reporting and underwriting risk .
- Independence & engagement: Confirmed independent; at least 80% meeting attendance; brings specialized insurance governance expertise .
- Pay alignment and safeguards: Modest cash retainer with equity grants that vest over time; clawback policy in place; plan prohibits repricing/backdating and excise tax gross-ups, which are shareholder-friendly .
- Related-party and conflicts: No related-party transactions disclosed involving Thompson; note her WTW Cayman leadership could present perceived conflicts if WTW interacts with OXBR, but none disclosed .
RED FLAGS
- CEO-Chairman duality persists (Madhu); board recognizes structure and maintains oversight, but combined roles often draw governance scrutiny .
- Voting power adjustment mechanics (9.9% cap) can complicate shareholder franchise and may create atypical voting outcomes .
- Disclosure inconsistency on 2024 director share grant counts (10,549 vs. 23,809) warrants clarification from IR .
Compensation Committee Analysis
- Members: Dwight Merren (Chair), Lesley Thompson, Arun Gowda; all independent and “non-employee directors” under 16b-3 .
- Consultant: Zayla Partners engaged for 2023 and going forward; peer groups used informationally to avoid pay “ratcheting” .
- Peer group examples (recent disclosures include broader peers): Atlantic American, Conifer, FG Financial, MBIA, eHealth, Paysign, Acacia Research, Waterstone Financial, Security National Financial, Citizens, Flexshopper, Regional Management, ICC Holdings, Reliance Global Group, Oportun Financial .
Related-Party Transactions
- No transactions disclosed involving Thompson. Related items involve CEO/CFO (e.g., HCI/TypTap, Jet.AI, OAC Sponsor, tokenized reinsurance), reviewed under Audit Committee policy .
Notes on Director Compensation Tables
| Name | Cash Fees | Stock Awards | Total (FY2024) |
|---|---|---|---|
| Lesley Thompson | $15,000 | $25,000 | $40,000 |
| Name | Cash Fees | Stock Awards | Total (FY2023) |
|---|---|---|---|
| Lesley Thompson | $15,000 | $25,000 | $40,000 |
Grant detail for 2024 (OXBR): 23,809 restricted shares on Jan 2, 2024, 50% vest at 180 days and 50% at first anniversary; plus 2,000 restricted shares in SP Holdings vesting ratably over 1 year from Mar 25, 2024 .
Additional Signals for Investors
- Board diversity: 1 female among 5 directors; matrix disclosed .
- Audit Committee properly reports independent auditor oversight and pre-approval policies .
- Clawback policy and anti-hedging policy disclosed and in force .
Appendix: Election Results (Recent)
- 2025 AGM director election: Lesley Thompson received 2,534,146 votes for, 122,698 against, 28 abstain; broker non-votes 2,315,191 .
- 2024 AGM director election: Lesley Thompson received 1,870,813 votes for, 91,248 against, 50,373 abstain; broker non-votes 2,047,016 .