Darryl Rawlings
TRUPANIONAbout Darryl Rawlings
Darryl Rawlings is Chair of the Board at Trupanion and the company’s founder and former CEO; he is age 55 and has served on the Board since 2000, with a diploma from the British Columbia Institute of Technology . He resigned as CEO effective August 1, 2024 and now serves as a non‑employee director and consultant to the company’s pet food initiative . The Board determined he is not independent due to his recent executive role and current consulting arrangement .
Past Roles
| Organization | Role | Tenure | Committees/Impact |
|---|---|---|---|
| Trupanion, Inc. | Founder; Chief Executive Officer (former) | CEO through Aug 1, 2024; Director since 2000 | Led IPO (2014) and expansion to U.S., Canada, Europe, Puerto Rico, Australia; subscription pets covered >1,000,000 and annual revenue exceeded $1B under his leadership |
External Roles
| Organization | Role | Tenure | Committees/Impact |
|---|---|---|---|
| NAPHIA (North American Pet Health Insurance Association) | Founder and member | Not disclosed | Industry advocacy; raising standards and awareness in pet insurance |
Board Governance
- Chair of the Board; not independent; no committee memberships .
- Lead Independent Director is Murray Low; he chairs independent director executive sessions and coordinates board agendas and stockholder consultation .
- 2024 activity and attendance: Board held 6 meetings; no director attended fewer than 75% of Board or relevant committee meetings during their service .
- Separation of roles: Following Rawlings’ resignation and Tooth’s appointment as CEO, Chair and CEO roles are held by different individuals, which the Board believes enhances oversight .
| Governance Item | Status | Evidence |
|---|---|---|
| Independence | Not independent | Recently CEO; current consultant |
| Board/Committee Assignments | Chair; no committees | “None” under committees for Rawlings |
| Lead Independent Director | Murray Low | Role and responsibilities detailed |
| Attendance | ≥75% threshold met (board-wide) | No director below 75% in 2024 |
Fixed Compensation (Director)
| Component | Amount | Timing/Terms | Notes |
|---|---|---|---|
| Annual director retainer | $150,000 | 2024 program | Payable in RSUs or cash; election options and limits per ownership guidelines |
| Additional chair retainer | $50,000 | 2024 program | Chair of Board; pro‑rated after becoming non‑employee director |
| RSU deferral option | N/A | Adopted Nov 2024 | Directors may elect to defer RSU settlement until board departure |
| Fees earned (Rawlings, 2024) | $83,290 | Prorated | Director and chair retainer paid in cash post‑CEO resignation |
| Other director fees (meeting fees) | None disclosed | 2024 | No meeting fees noted |
Performance Compensation (Executive context during 2024 service)
Rawlings had executive compensation prior to Aug 1, 2024, including short‑term incentives and equity grants.
- Short‑term incentive (legacy plan, Jan–Jun 2024): Corporate metrics included Gross New Pets Under Three, Cancellations, and Subscription Adjusted Operating Income; monthly achievement averaged 38% (AOI 25%, cancellations 17%, gross new pets under three <1%) . Rawlings’ H1 target was $60,000; earned $22,744, paid in cash .
- Management Incentive Plan (MIP, Jul–Dec 2024): Metrics were Adjusted Operating Income (AOI), Lifetime Value per Pet (LVP), Internal Rate of Return (IRR); company payout was 106% of target driven by LVP (200%) and IRR (92%), offset by AOI (65%). Rawlings did not transition to the MIP and had only a July legacy period target; earned $4,640 .
| Metric (Legacy/MIP) | Definition | Why It Matters |
|---|---|---|
| Subscription Adjusted Operating Income (AOI) | Profit from an existing pet before new pet acquisition investment | Funds pet acquisition and growth initiatives |
| Gross New Pets Under Three | New enrollments for pets under age three | Drives revenue growth, LVP, and IRR |
| Cancellations | Number of cancelled pets | Affects growth, LVP, and IRR negatively |
| Total Adjusted Operating Income (AOI) | Non‑GAAP AOI excluding acquisition, development, nonrecurring items and certain non‑cash charges | Reflects pricing, expense discipline, subscriber growth/retention |
| Lifetime Value per Pet (LVP) | 36‑month margin per pet minus allocated fixed expenses times implied subscriber life | Measures ARPU, retention, profit per insured pet |
| Internal Rate of Return (IRR) | Discount rate equating lifetime cash flows of new pet to acquisition cost | Captures disciplined PAC spend, ARPU, retention, profit |
| 2024 Short‑Term Incentives (Rawlings) | Target Opportunity | Achievement | Earned | Delivery |
|---|---|---|---|---|
| Jan–Jun (Legacy) | $60,000 | 38% | $22,744 | Cash only |
| Jul (Legacy, no MIP transition) | $10,000 | 46% | $4,640 | Cash only |
| 2024 Equity Grants (awarded Feb 2024) | Type | Shares | Vesting | Notes |
|---|---|---|---|---|
| Spot bonus | RSUs | 5,000 | 4 years | Granted while CEO |
| Performance year 2023 | RSUs | 50,000 | 2 years | Granted for 2023 performance; reported in 2024 SCT as stock awards ($1,363,500) |
Other Directorships & Interlocks
| Entity | Type | Role | Potential Interlock/Conflict |
|---|---|---|---|
| Public company boards | — | None disclosed | No other public boards listed in biography |
| Aflac Incorporated | Strategic investor | Aflac holds ~8.50% of TRUP; Aflac’s CFO (Max Brodén) sits on TRUP’s Board | Board reviewed independence considering Aflac alliance and director affiliations; determined Brodén is independent |
| Family relationships | Territory Partners | Father (David Sr.) and brother (David Jr.) are Territory Partners paid CAN$228,351 and CAN$97,178 respectively (2024) | Related‑party transactions disclosed; standard independent contractor roles |
Expertise & Qualifications
- Founder of Trupanion with >20 years building the pet medical insurance industry; led 2014 IPO and geographic expansion to U.S., Canada, Europe, Puerto Rico, Australia; subscription base >1,000,000 pets; annual revenue topped $1B under his leadership .
- Industry leadership via NAPHIA founder/member; mission‑focused on improving veterinary care access .
- Education: British Columbia Institute of Technology .
Equity Ownership
| Holder/Instrument | Shares | % of Outstanding | Notes |
|---|---|---|---|
| Direct (Rawlings) | 623,671 | — | Directly held |
| Kuyashii Primary Equities LLC | 857,809 | — | Wholly‑owned subsidiary of Kuyashii, LLC (Rawlings and spouse are sole members); Rawlings has sole voting/investment power |
| Options exercisable ≤60 days | 5,448 | — | Options currently exercisable |
| RSUs vesting ≤60 days | 7,507 | — | RSUs scheduled to vest |
| Total beneficial ownership | 1,494,435 | 3.49% | Based on 42,776,104 shares outstanding (record date Apr 16, 2025) |
| Excluded trust holdings | 200,000 | — | Rawlings GST Trust; trustee is director Murray Low; beneficiaries are Rawlings’ children via Trust Beneficiaries |
Policies:
- Company prohibits hedging and limits pledging via Insider Trading Policy and Pledging Guidelines for Directors and Officers . No pledging or hedging by Rawlings is disclosed in the proxy.
Employment & Contracts (Consulting)
| Agreement | Compensation | Term | Termination | Notes |
|---|---|---|---|---|
| Consulting agreement (pet food initiative) | $200,000 per annum; paid monthly; plus potential equity awards and other remuneration at committee discretion | Initial one‑year; auto‑renews annually | Rawlings may terminate any time; Company may terminate with 10 days’ notice | $83,333 paid in 2024 under the agreement |
Compensation Committee Analysis (Board context)
- Compensation Committee members: Richard Enthoven, Betsy McLaughlin, Howard Rubin (Chair); independent under NASDAQ/SEC rules .
- Use of independent consultants: Meridian engaged in 2024; replaced by Willis Towers Watson effective Jan 1, 2025; committee assessed both as independent and conflict‑free .
- Say‑on‑pay support: ~96.4% approval at 2024 Annual Meeting .
Governance Assessment
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Strengths:
- Significant equity ownership (3.49%) aligns Rawlings with stockholder outcomes .
- Clear separation of Chair and CEO roles since Aug 2024; active Lead Independent Director oversight and independent committee structures .
- Robust governance policies (Code of Conduct, clawbacks beyond SEC/NASDAQ, hedging ban, pledging limits) .
-
Concerns and potential RED FLAGS:
- Not independent due to recent CEO tenure and ongoing paid consulting while serving as Chair; may affect perceived board independence .
- Related‑party transactions with immediate family (father and brother) as Territory Partners; while disclosed and consistent with program, they constitute related‑party exposure .
- Trust holdings excluded from Rawlings’ beneficial ownership where the trustee is the Lead Independent Director (Murray Low); while common in estate planning, investor scrutiny may consider governance optics of director‑linked trust structures .
- Director compensation elections: Rawlings elected cash only for retainer in 2024 (post‑CEO), reducing incremental annual equity accumulation from director service; however, his pre‑existing ownership is substantial .
Overall, Rawlings brings deep domain expertise and substantial ownership alignment, but continued consulting during his chairmanship and family related‑party interactions warrant monitoring for conflicts and board independence perceptions .