Hippo Holdings Inc. — Insider Transactions
Form 4 filings by directors, officers, and 10%+ shareholders
SEC rules require corporate insiders — including directors, executive officers, and any shareholder owning more than 10% of a company's shares — to report changes in their ownership within two business days of a transaction. These disclosures are filed as Form 4. Open-market purchases (code P) are generally considered the most meaningful signal, as insiders are spending their own money.
| Insider | Title | Type | Shares | Price | Value | Owns After | Date |
|---|---|---|---|---|---|---|---|
| Stienstra Michael | GM & Chief Insurance, HHIP | Sale | 3,900 | $31.12 | $121,368 | 71,281 | Dec 22, 2025 |
| NICHOLS JOHN DRAKE | — | Gift | 4,935 | — | — | 16,563 | Dec 18, 2025 |
| McCathron Richard | Chief Executive Officer | Sale | 5,000 | $29.82 | $149,100 | 452,704 | Dec 9, 2025 |
| Ostergaard Torben | CEO Spinnaker | Sale | 152 | $32.63 | $4,960 | 55,207 | Nov 21, 2025 |
| Zeltser Guy | Chief Financial Officer | Tax Withholding | 4,182 | $31.11 | $130,102 | 70,679 | Nov 18, 2025 |
| Stienstra Michael | GM & Chief Insurance, HHIP | Tax Withholding | 2,463 | $31.11 | $76,624 | 75,181 | Nov 15, 2025 |
| Ostergaard Torben | CEO Spinnaker | Tax Withholding | 2,123 | $31.11 | $66,047 | 58,852 | Nov 15, 2025 |
| McCathron Richard | Chief Executive Officer | Tax Withholding | 11,326 | $31.11 | $352,352 | 457,704 | Nov 15, 2025 |
| Hay Laura J | — | Award / Grant | 2,502 | — | — | 2,502 | Oct 1, 2025 |
| Holliday Susan Claire | — | Award / Grant | 2,502 | — | — | 2,502 | Oct 1, 2025 |
| Zeltser Guy | Chief Financial Officer | Sale | 4,977 | $37.46 | $186,438 | 75,061 | Sep 17, 2025 |
| Stienstra Michael | GM & Chief Insurance, HHIP | Tax Withholding | 752 | $36.97 | $27,801 | 77,644 | Sep 10, 2025 |
| Ostergaard Torben | CEO Spinnaker | Tax Withholding | 1,358 | $36.97 | $50,205 | 60,975 | Sep 10, 2025 |
| Zeltser Guy | Chief Financial Officer | Tax Withholding | 1,029 | $36.97 | $38,042 | 80,038 | Sep 10, 2025 |
| McCathron Richard | Chief Executive Officer | Tax Withholding | 1,358 | $36.97 | $50,205 | 469,030 | Sep 10, 2025 |
| McCathron Richard | Chief Executive Officer | Sale | 2,725 | $34.12 | $92,977 | 470,388 | Sep 8, 2025 |
| McCathron Richard | Chief Executive Officer | Sale | 2,275 | $34.00 | $77,350 | 473,113 | Aug 22, 2025 |
| Stienstra Michael | GM & Chief Insurance, HHIP | Tax Withholding | 2,341 | $30.91 | $72,360 | 78,396 | Aug 15, 2025 |
| Ostergaard Torben | CEO Spinnaker | Tax Withholding | 2,016 | $30.91 | $62,315 | 62,333 | Aug 15, 2025 |
| Zeltser Guy | Chief Financial Officer | Tax Withholding | 3,973 | $30.91 | $122,805 | 81,067 | Aug 15, 2025 |
| McCathron Richard | Chief Executive Officer | Tax Withholding | 10,759 | $30.91 | $332,561 | 475,388 | Aug 15, 2025 |
| Len FW Investor, LLC | — | Other | 81,900 | — | — | 2,990,727 | Jul 1, 2025 |
| Ostergaard Torben | CEO Spinnaker | Sale | 2,444 | $29.95 | $73,198 | 64,349 | Jun 12, 2025 |
| Ostergaard Torben | CEO Spinnaker | Sale | 4,889 | $24.61 | $120,318 | 66,793 | Jun 4, 2025 |
| NICHOLS JOHN DRAKE | — | Award / Grant | 5,801 | $24.35 | $141,254 | 16,760 | Jun 3, 2025 |
| WIJNBERG SANDRA S | — | Award / Grant | 5,801 | $24.35 | $141,254 | 17,077 | Jun 3, 2025 |
| Landman Sam | — | Award / Grant | 5,801 | $24.35 | $141,254 | 19,534 | Jun 3, 2025 |
| Fouche Lori Dickerson | — | Award / Grant | 4,738 | — | — | 21,815 | Jun 3, 2025 |
| FRATER HUGH R | — | Award / Grant | 5,801 | $24.35 | $141,254 | 17,077 | Jun 3, 2025 |
| Feder Eric | — | Award / Grant | 5,801 | $24.35 | $141,254 | 17,077 | Jun 3, 2025 |
| Schaaf Mark | — | Award / Grant | 5,801 | $24.35 | $141,254 | 11,365 | Jun 3, 2025 |
| Ostergaard Torben | CEO Spinnaker | Tax Withholding | 3,602 | $22.10 | $79,604 | 71,682 | May 15, 2025 |
| Stienstra Michael | GM & Chief Insurance, HHIP | Tax Withholding | 2,876 | $22.10 | $63,560 | 80,737 | May 15, 2025 |
| McCathron Richard | Chief Executive Officer | Tax Withholding | 10,760 | $22.10 | $237,796 | 486,147 | May 15, 2025 |
| Zeltser Guy | Chief Financial Officier | Tax Withholding | 3,972 | $22.10 | $87,781 | 85,040 | May 14, 2025 |
| Wand Assaf | Executive Chairman BoD | Sale | 12,250 | $25.04 | $306,740 | 474,564 | Apr 1, 2025 |
| McCathron Richard | Chief Executive Officer | Award / Grant | 56,326 | — | — | 496,907 | Mar 5, 2025 |
| Stienstra Michael | GM & Chief Insurance, HHIP | Award / Grant | 23,965 | — | — | 83,613 | Mar 4, 2025 |
| Ostergaard Torben | CEO Spinnaker | Award / Grant | 23,965 | — | — | 75,284 | Mar 4, 2025 |
| Ellis Stewart | CFO/ Chief Strategy Officer | Award / Grant | 42,794 | — | — | 346,545 | Mar 4, 2025 |
| Wand Assaf | Executive Chairman BoD | Sale | 12,250 | $28.90 | $354,025 | 486,814 | Mar 3, 2025 |
| Stienstra Michael | GM & Chief Insurance, HHIP | Tax Withholding | 3,031 | $30.11 | $91,263 | 61,977 | Feb 18, 2025 |
| Ostergaard Torben | CEO Spinnaker | Tax Withholding | 3,516 | $30.11 | $105,867 | 51,319 | Feb 15, 2025 |
| Ellis Stewart | CFO/ Chief Strategy Officer | Tax Withholding | 14,464 | $30.11 | $435,511 | 303,751 | Feb 15, 2025 |
| McCathron Richard | Chief Executive Officer | Tax Withholding | 11,693 | $30.11 | $352,076 | 327,930 | Feb 15, 2025 |
| Ostergaard Torben | CEO Spinnaker | Sale | 21,146 | $30.05 | $635,437 | 74,120 | Feb 5, 2025 |
| Wand Assaf | Executive Chairman BoD | Sale | 8,048 | $26.52 | $213,433 | 503,266 | Feb 3, 2025 |
| Ostergaard Torben | CEO Spinnaker | Sale | 3,022 | $27.25 | $82,350 | 95,266 | Jan 29, 2025 |
| Ostergaard Torben | CEO Spinnaker | Sale | 3,022 | $25.77 | $77,877 | 98,288 | Jan 8, 2025 |
| Wand Assaf | Executive Chairman BoD | Sale | 3,754 | $26.51 | $99,519 | 511,314 | Jan 2, 2025 |