As of August 29, 2026, Hippo Holdings's top three insider holders are Fw Investor, Llc Len (TenPercentOwner, 2.91Mn shares), Assaf Wand (Director, 686.07K shares), Richard Mccathron (Chief Executive Officer, 572.13K shares).
| # | Insider | Position | Direct | Indirect | Total | Share of Insiders | Last Filed |
|---|---|---|---|---|---|---|---|
| 1 | Fw Investor, Llc Len | TenPercentOwner | 72,720,726 | 0 | 72,720,726 | 87.7% | 19 Aug, 2022 |
| 2 | Sponsor Z Llc Reinvent | Other | 5,630,000 | 0 | 5,630,000 | 6.8% | 03 Aug, 2021 |
| 3 | Mark J Pincus | Other | 0 | 1,000,000 | 1,000,000 | 1.2% | 03 Aug, 2021 |
| 4 | Wall Ventures Management Gp, Llc Fifth | TenPercentOwner | 0 | 961,882 | 961,882 | 1.2% | 18 Aug, 2022 |
| 5 | Richard Mccathron | Chief Executive Officer | 572,132 | 0 | 572,132 | 0.7% | 18 Aug, 2026 |
| 6 | Assaf Wand | Executive Chairman Bod | 0 | 474,564 | 474,564 | 0.6% | 03 Apr, 2025 |
| 7 | Aviad Pinkovezky | Chief Product Officer | 283,290 | 0 | 283,290 | 0.3% | 17 Feb, 2022 |
| 8 | Ran Harpaz | Chief Operating Officer | 162,599 | 0 | 162,599 | 0.2% | 17 Nov, 2022 |
| 9 | Stewart Ellis | Director | 126,455 | 0 | 126,455 | 0.2% | 19 Aug, 2026 |
| 10 | Guy Zeltser | Chief Financial Officer | 116,618 | 0 | 116,618 | 0.1% | 18 Aug, 2026 |
| 11 | Anirudh Badia | Chief Accounting Officer | 102,315 | 0 | 102,315 | 0.1% | 08 Nov, 2024 |
| 12 | Yuval Harry | Chief Revenue Officer | 97,251 | 0 | 97,251 | 0.1% | 22 Oct, 2024 |
| 13 | Christopher Donahue | General Manager, Mga Cuo | 95,019 | 0 | 95,019 | 0.1% | 16 Nov, 2023 |
| 14 | Michael Stienstra | Gm Chief Insurance, Hhip | 89,901 | 0 | 89,901 | 0.1% | 18 Aug, 2026 |
| 15 | Laura Boettcher | Chief Operating Officer | 71,381 | 0 | 71,381 | 0.1% | 18 Aug, 2026 |
| 16 | Simon Fleming-Wood | Chief Marketing Officer | 66,068 | 0 | 66,068 | 0.1% | 17 May, 2023 |
| 17 | Torben Ostergaard | Ceo Spinnaker | 61,824 | 0 | 61,824 | 0.1% | 18 Aug, 2026 |
| 18 | Lee Linden | Other | 30,000 | 0 | 30,000 | 0.0% | 03 Aug, 2021 |
| 19 | Linda Rottenberg | Other | 30,000 | 0 | 30,000 | 0.0% | 03 Aug, 2021 |
| 20 | Sam Landman | Director | 29,080 | 0 | 29,080 | 0.0% | 04 Jun, 2026 |
| 21 | Hugh R Frater | Director | 26,623 | 0 | 26,623 | 0.0% | 04 Jun, 2026 |
| 22 | Lori Dickerson Fouche | Director | 26,623 | 0 | 26,623 | 0.0% | 04 Jun, 2026 |
| 23 | Eric Feder | Director | 21,815 | 0 | 21,815 | 0.0% | 04 Jun, 2026 |
| 24 | John Drake Nichols | Director | 21,371 | 0 | 21,371 | 0.0% | 04 Jun, 2026 |
| 25 | Mark Schaaf | Director | 20,911 | 0 | 20,911 | 0.0% | 04 Jun, 2026 |
| 26 | Noah Knauf | Director | 11,794 | 0 | 11,794 | 0.0% | 09 Jun, 2023 |
| 27 | Amy Errett | Director | 11,276 | 0 | 11,276 | 0.0% | 04 Aug, 2023 |
| 28 | Laura J Hay | Director | 7,310 | 0 | 7,310 | 0.0% | 04 Jun, 2026 |
| 29 | Susan Claire Holliday | Director | 7,310 | 0 | 7,310 | 0.0% | 04 Jun, 2026 |
Each row is that insider’s most recently reported position, from Form 4 filings over the last 60 months — which is why this total does not tie to the quarterly series above, where a quarter counts only the insiders who filed in it. Shares held through a fund or institutional portfolio are counted on the institutional ownership page instead.
| Date | Insider | Position | Transaction | Shares | Price | Value | Shares Held After | Ownership |
|---|---|---|---|---|---|---|---|---|
| 15 Aug, 2026 | Stewart Ellis | Director | Acquired A | 5,350 | $33.04 | $176.76K | 126,455 | Direct |
| 15 Aug, 2026 | Richard Mccathron | Chief Executive Officer | Disposed F | 8,301 | $32.83 | $272.49K | 572,132 | Direct |
| 15 Aug, 2026 | Laura Boettcher | Chief Operating Officer | Disposed F | 1,586 | $32.83 | $52.06K | 71,381 | Direct |
| 15 Aug, 2026 | Michael Stienstra | Gm Chief Insurance, Hhip | Disposed F | 1,259 | $32.83 | $41.33K | 89,901 | Direct |
| 15 Aug, 2026 | Guy Zeltser | Chief Financial Officer | Disposed F | 3,945 | $32.83 | $129.50K | 116,618 | Direct |
| 15 Aug, 2026 | Torben Ostergaard | Ceo Spinnaker | Disposed F | 1,340 | $32.83 | $43.99K | 62,993 | Direct |
| 17 Aug, 2026 | Torben Ostergaard | Ceo Spinnaker | Disposed S | 1,169 | $33.00 | $38.58K | 61,824 | Direct |
| 10 Aug, 2026 | Richard Mccathron | Chief Executive Officer | Disposed S | 5,000 | $32.00 | $160.00K | 580,433 | Direct |
| 28 Jul, 2026 | Guy Zeltser | Chief Financial Officer | Disposed S | 1,669 | $30.98 | $51.71K | 120,563 | Direct |
| 09 Jul, 2026 | Richard Mccathron | Chief Executive Officer | Disposed S | 5,000 | $28.53 | $142.65K | 585,433 | Direct |
| 10 Jun, 2026 | Laura Boettcher | Chief Operating Officer | Acquired A | 11,674 | $0.00 | $0 | 72,967 | Direct |
| 09 Jun, 2026 | Richard Mccathron | Chief Executive Officer | Disposed S | 5,000 | $25.00 | $125.00K | 590,433 | Direct |
| 03 Jun, 2026 | Stewart Ellis | Director | Acquired A | 4,820 | $0.00 | $0 | 121,105 | Direct |
| 02 Jun, 2026 | Laura J Hay | Director | Acquired A | 2,502 | $25.40 | $63.55K | 2,502 | Direct |
| 02 Jun, 2026 | Mark Schaaf | Director | Acquired A | 4,738 | $25.40 | $120.35K | 16,103 | Direct |
| 02 Jun, 2026 | Lori Dickerson Fouche | Director | Acquired A | 4,738 | $25.40 | $120.35K | 21,815 | Direct |
| 02 Jun, 2026 | Eric Feder | Director | Acquired A | 4,738 | $25.40 | $120.35K | 21,815 | Direct |
| 02 Jun, 2026 | Hugh R Frater | Director | Acquired A | 4,738 | $25.40 | $120.35K | 21,815 | Direct |
| 02 Jun, 2026 | Susan Claire Holliday | Director | Acquired A | 2,502 | $25.40 | $63.55K | 2,502 | Direct |
| 02 Jun, 2026 | Sam Landman | Director | Acquired A | 4,738 | $25.40 | $120.35K | 24,272 | Direct |