Michael Stienstra
About Michael Stienstra
Michael Stienstra is Hippo’s Chief Insurance Officer and General Manager of the Hippo Home Insurance Program (HHIP) since January 2024, and previously served as Hippo’s Chief Actuary starting April 2021 . He is 40 years old , holds a BBA in Actuarial Science and Mathematics from the University of Wisconsin–Madison and an MBA from Northwestern University’s Kellogg School (Marketing and Finance concentrations) . Prior to Hippo, he was Senior Vice President leading the actuarial team for Personal Risk Services at Chubb (Oct 2018–Apr 2021) , and earlier held senior underwriting/actuarial roles (including at ACE and AIG) and chaired the Casualty Actuarial Society Task Force on Automated Vehicles . Under his tenure within HHIP leadership, Investor Day materials highlight portfolio repricing, lower loss costs, and significant loss ratio improvement since 2022 .
Past Roles
| Organization | Role | Years | Strategic Impact |
|---|---|---|---|
| Hippo Holdings Inc. | Chief Actuary | Apr 2021–Jan 2024 | Built actuarial foundation supporting portfolio repricing and loss ratio improvement . |
| Chubb (Personal Risk Services) | Senior Vice President, Actuarial Team Lead | Oct 2018–Apr 2021 | Led personal lines actuarial team; deep homeowners pricing/underwriting experience . |
External Roles
| Organization | Role | Years | Strategic Impact |
|---|---|---|---|
| Casualty Actuarial Society | Chair, Task Force on Automated Vehicles | Not disclosed | Industry leadership on evolving risk topics (automated vehicles) . |
Fixed Compensation
- Hippo is an “emerging growth company” and discloses scaled executive compensation for NEOs only; Stienstra is not a named executive officer in 2024 disclosures, so base salary/bonus specifics are not disclosed .
Performance Compensation
- Not specifically disclosed for Stienstra. The 2024 incentive framework described in the proxy applied to NEOs (50% service/retention; 50% company/individual performance with committee discretion), and cannot be assumed for Stienstra without specific disclosure .
Equity Ownership & Alignment
- Anti-hedging policy prohibits hedging transactions (e.g., collars, swaps, exchange funds), aligning incentives with shareholders for officers including Section 16 insiders .
- Clawback policy (effective Oct 2, 2023) requires recoupment of erroneously received incentive-based compensation for Section 16 officers over the preceding three fiscal years upon an accounting restatement .
Ownership evolution snapshots
| Metric | 02/20/2024 | 02/18/2025 | 08/15/2025 | 09/10/2025 |
|---|---|---|---|---|
| Beneficially owned shares (post-transaction or reported) | 12,036 | 59,648 (incl. 36,489 RSUs) | 78,396 (incl. 46,271 RSUs) | 77,644 (incl. 44,246 RSUs) |
Insider transactions and vesting-related dispositions
| Date | Transaction Code | Shares | Price | Notes |
|---|---|---|---|---|
| 02/15/2025 | F (disposition) | 3,031 | $30.11 | Disposition at vest; RSU-related per summary text . |
| 02/18/2025 | S (sale under plan) | 2,329 | $30.0186 | 10b5-1 sale; multi-trade weighted average . |
| 08/15/2025 | F (disposition) | 2,341 | $30.91 | RSU-related disposition; post-transaction ownership 78,396 (incl. 46,271 RSUs) . |
| 09/10/2025 | S (sale) | 752 | $36.97 | Post-transaction ownership 77,644 (incl. 44,246 RSUs) . |
| 11/15/2025 | F (disposition) | 2,463 | $31.1137 | RSU-related disposition . |
Trading arrangements and expected vesting
| Item | Details |
|---|---|
| Rule 10b5-1 plan adoption | Adopted 09/21/2025; plan to sell up to 43,290 shares through 09/30/2026; includes sale of up to 9,892 RSUs expected to vest during the plan term . |
| Late Section 16 filings (admin error) | One Form 4 for refresh RSUs was filed late for several executives including Stienstra . |
- Pledging: No explicit pledging policy disclosure; anti-hedging policy in place .
Employment Terms
- Insider Trading Policy filed as exhibit to the 2024 Form 10-K governs directors/officers; aligns with NYSE standards .
- Anti-hedging policy prohibits hedging instruments that misalign incentives .
- Compensation clawback policy effective Oct 2, 2023 for Section 16 officers .
- Specific employment agreement terms (non-compete, severance, change-in-control) for Stienstra are not disclosed; proxy references such arrangements for certain executives generally, but no executive-specific contract for Stienstra is provided .
Performance & Track Record
- HHIP portfolio transformation shows repricing and loss cost reduction: average premiums up ~45%, loss costs down >20% (ex-cat and cat) since 2022 .
- Rating improvements included 18 new variables; worst risks saw >200% increases while best risks saw 5–25% decreases .
- Underwriting year performance (Ultimate Loss and ALAE %) indicates sustained improvement.
| Metric | 2018 | 2019 | 2020 | 2021 | 2022 | 2023 | 2024E |
|---|---|---|---|---|---|---|---|
| HHIP Ultimate Loss & ALAE (%) | 130% | 125% | 121% | 102% | 98% | 83% | 54–32–3–15% (chart sequence; 2024E points shown across categories in slide) |
Note: 2024E chart points show multiple plotted values; slide indicates broad improvement trajectory rather than a single consolidated ratio .
Compensation Structure Analysis
- Pay-for-performance alignment signals: RSU vesting reported via Form 4 “F” dispositions; presence of a Rule 10b5-1 plan mitigates discretionary timing concerns and suggests pre-scheduled sales tied to vesting .
- Governance overlays (clawback, anti-hedging) strengthen alignment with long-term shareholder outcomes .
Risk Indicators & Red Flags
- Late filing instance for a refresh RSU Form 4 due to administrative error was noted across several executives including Stienstra .
- No disclosures of hedging or exchange fund use permitted (prohibited); pledging not disclosed .
- No legal proceedings or investigations pertaining to Stienstra are disclosed in the cited filings.
Expertise & Qualifications
- 19+ years of relevant insurance/actuarial experience; deep underwriting and actuarial leadership across CHUBB/ACE/AIG prior to Hippo .
- MBA (Kellogg) and actuarial training (UW–Madison), aligning with technical risk selection and portfolio management competencies .
Equity Ownership & Alignment (Summary)
- Initial Form 3 reported 12,036 shares owned (Feb 2024) .
- Subsequent beneficial ownership increased through 2025 alongside RSU vesting; multiple “F” dispositions and plan-governed sales executed, with RSU components explicitly noted in filings .
Investment Implications
- Execution track record: HHIP underwriting improvements (repricing, lower loss costs, enhanced rating variables) support improved economics and margin recovery under Stienstra’s operational purview .
- Insider selling pressure: A Rule 10b5-1 plan adopted 09/21/2025 contemplates up to 43,290 shares sold through 09/30/2026, including up to 9,892 expected-to-vest RSUs—anticipate periodic F-code disposals at vesting and scheduled sales, which can add predictable, modest supply to the float .
- Alignment: Anti-hedging and clawback frameworks reduce governance risk; absence of disclosed pledging is a positive, though explicit pledging policy is not stated .
- Data gaps: No disclosed base salary/bonus/severance/change-in-control terms for Stienstra due to EGC-scaled proxy and non-NEO status; monitor future 8-K Item 5.02 filings and Form 4s for continued visibility .