HIPO · Insider Trading
Hippo Holdings Inc.
Every open-market purchase and sale reported by HIPO officers, directors and 10%+ beneficial owners on SEC Form 4, which must be filed within two business days of the transaction. Sales often reflect scheduled 10b5-1 plans or tax withholding rather than a directional view, so read counts alongside the size and the filer.
| Filed | Insider | Role | Type | Shares | Value |
|---|---|---|---|---|---|
| 2026-10-16 | Torben Ostergaard | CEO Spinnaker | Sell | −1,169 | −$40.96K |
| 2026-10-13 | Richard McCathron | Chief Executive Officer | Sell | −5,000 | −$170.90K |
| 2026-09-11 | Richard McCathron | Chief Executive Officer | Sell | −5,000 | −$161.15K |
| 2026-08-19 | Stewart Ellis | Director | A | +5,350 | +$176.76K |
| 2026-08-18 | Richard McCathron | Chief Executive Officer | F | −8,301 | −$272.49K |
| 2026-08-18 | Torben Ostergaard | CEO Spinnaker | MIXED | −2,509 | −$82.56K |
| 2026-08-18 | Michael Stienstra | GM & Chief Insurance, HHIP | F | −1,259 | −$41.33K |
| 2026-08-18 | Guy Zeltser | Chief Financial Officer | F | −3,945 | −$129.50K |
| 2026-08-18 | Laura Boettcher | Chief Operating Officer | F | −1,586 | −$52.06K |
| 2026-08-12 | Richard McCathron | Chief Executive Officer | Sell | −5,000 | −$160.00K |
| 2026-07-30 | Guy Zeltser | Chief Financial Officer | Sell | −1,669 | −$51.71K |
| 2026-07-13 | Richard McCathron | Chief Executive Officer | Sell | −5,000 | −$142.65K |
| 2026-06-12 | Laura Boettcher | Chief Operating Officer | A | +11,674 | — |
| 2026-06-11 | Richard McCathron | Chief Executive Officer | Sell | −5,000 | −$125.00K |
| 2026-06-05 | Stewart Ellis | Director | A | +4,820 | — |
| 2026-06-04 | Lori Dickerson Fouche | Director | A | +9,546 | +$120.35K |
| 2026-06-04 | Eric Feder | Director | A | +4,738 | +$120.35K |
| 2026-06-04 | Sam Landman | Director | A | +9,546 | +$120.35K |
| 2026-06-04 | Hugh R Frater | Director | A | +9,546 | +$120.35K |
| 2026-06-04 | Laura J Hay | Director | A | +7,310 | +$63.55K |
| 2026-06-04 | John Drake Nichols | Director | A | +9,546 | +$120.35K |
| 2026-06-04 | Mark Schaaf | Director | A | +9,546 | +$120.35K |
| 2026-06-04 | Sandra S Wijnberg | Director | A | +9,546 | +$120.35K |
| 2026-06-04 | Susan Claire Holliday | Director | A | +7,310 | +$63.55K |
| 2026-05-19 | Richard McCathron | Chief Executive Officer | F | −8,779 | −$231.87K |
| 2026-05-19 | Torben Ostergaard | CEO Spinnaker | MIXED | −5,007 | −$131.10K |
| 2026-05-19 | Guy Zeltser | Chief Financial Officer | MIXED | −3,426 | −$93.23K |
| 2026-05-19 | Michael Stienstra | GM & Chief Insurance, HHIP | F | −1,259 | −$33.25K |
| 2026-05-13 | Richard McCathron | Chief Executive Officer | Sell | −5,000 | −$135.50K |
| 2026-04-29 | Richard McCathron | Chief Executive Officer | F | −1,438 | −$40.56K |
| 2026-04-29 | Torben Ostergaard | CEO Spinnaker | F | −1,438 | −$40.56K |
| 2026-04-29 | Michael Stienstra | GM & Chief Insurance, HHIP | F | −794 | −$22.40K |
| 2026-04-29 | Guy Zeltser | Chief Financial Officer | F | −1,091 | −$30.78K |
| 2026-04-13 | Richard McCathron | Chief Executive Officer | Sell | −5,000 | −$130.25K |
| 2026-03-11 | Richard McCathron | Chief Executive Officer | Sell | −5,000 | −$129.30K |
| 2026-03-05 | Richard McCathron | Chief Executive Officer | A | +189,532 | — |
| 2026-03-05 | Guy Zeltser | Chief Financial Officer | A | +61,707 | — |
| 2026-03-05 | Michael Stienstra | GM & Chief Insurance, HHIP | A | +24,684 | — |
| 2026-03-05 | Torben Ostergaard | CEO Spinnaker | A | +24,684 | — |
| 2026-02-27 | Torben Ostergaard | CEO Spinnaker | Sell | −600 | −$18.27K |
| 2026-02-18 | Michael Stienstra | GM & Chief Insurance, HHIP | F | −2,752 | −$78.68K |
| 2026-02-18 | Guy Zeltser | Chief Financial Officer | MIXED | −3,818 | −$123.37K |
| 2026-02-18 | Richard McCathron | Chief Executive Officer | F | −11,586 | −$331.27K |
| 2026-02-18 | Torben Ostergaard | CEO Spinnaker | MIXED | −8,513 | −$243.24K |
| 2026-02-11 | Richard McCathron | Chief Executive Officer | Sell | −5,000 | −$145.70K |
| 2026-01-13 | Richard McCathron | Chief Executive Officer | Sell | −5,000 | −$157.60K |
| 2025-12-29 | Michael Stienstra | GM & Chief Insurance, HHIP | Sell | −3,900 | −$121.37K |
| 2025-12-19 | John Drake Nichols | Director | G | −4,935 | — |
| 2025-12-11 | Richard McCathron | Chief Executive Officer | Sell | −5,000 | −$149.10K |
| 2025-11-25 | Torben Ostergaard | CEO Spinnaker | Sell | −3,645 | −$116.59K |
| Insider | Role | Shares Held | Value |
|---|---|---|---|
| Len FW Investor, LLC | — | 2,476,418 | $95.12M |
| Assaf Wand | Executive Chairman BoD | 1,158,081 | $44.48M |
| Richard McCathron | Chief Executive Officer | 562,132 | $21.59M |
| Stewart Ellis | CFO/ Chief Strategy Officer | 136,790 | $5.25M |
| Guy Zeltser | Chief Financial Officer | 116,618 | $4.48M |
| Anirudh Badia | Chief Accounting Officer | 102,315 | $3.93M |
| Michael Stienstra | GM & Chief Insurance, HHIP | 89,901 | $3.45M |
| Laura Boettcher | Chief Operating Officer | 71,441 | $2.74M |
| John Drake Nichols | Director | 66,563 | $2.56M |
| Hugh R Frater | Director | 64,869 | $2.49M |
| Torben Ostergaard | CEO Spinnaker | 60,655 | $2.33M |
| Sandra S Wijnberg | Director | 31,303 | $1.20M |
| Sam Landman | Director | 29,080 | $1.12M |
| Eric Feder | Director | 26,815 | $1.03M |
| Lori Dickerson Fouche | Director | 21,815 | $837.91K |
| Mark Schaaf | Director | 20,911 | $803.19K |
| Laura J Hay | Director | 2,502 | $96.10K |
| Susan Claire Holliday | Director | 2,502 | $96.10K |
Form 4 reports a change in beneficial ownership by an officer, director or 10%+ holder, and must be filed within two business days of the transaction — so this is close to real time, unlike the 45-day-lagged 13F institutional data.
Transaction codes matter more than the raw buy/sell count. Code P is an open-market purchase — an insider choosing to buy with their own money, which is the signal most research treats as informative. Code S is a sale, but sales are frequently pre-scheduled under a 10b5-1 plan or cover tax withholding on vesting equity, so a run of sales often says nothing directional. Codes A and M are grants and option exercises rather than open-market decisions.
Full filing history and per-insider positions are on the HIPO quote page; the site-wide leaderboard is on the insider transactions hub.
Market data may be delayed, incomplete, or inaccurate. Not a recommendation to buy, sell, or hold any security. Verify quotes with your broker before trading. See Terms §17.