HIPO Insider Trading
Hippo Holdings Inc. | Fire, Marine & Casualty Insurance
Comprehensive Trading Performance Summary
The investment history of corporate insiders at Hippo Holdings Inc. provides a unique lens into the internal conviction of the company's leadership. By analyzing SEC Form 4 filings, investors can track how directors and officers are allocating their own capital. High-conviction buying often signals that management believes the current market price significantly undervalues future growth prospects, while strategic selling might occur for personal liquidity or portfolio diversification. Monitoring these shifts in ownership is essential for understanding the alignment between management and shareholders in the Fire, Marine & Casualty Insurance sector.
Transactions on Chart
Open Full Chart| Filing Date | Trade Date | Reporting Person | Relationship | Type | Price | Qty | Total, $ | Owned After | Change, % |
|---|---|---|---|---|---|---|---|---|---|
| 2026-03-11 21:06 | 2026-03-09 | McCathron Richard | Director, Officer - Chief Executive Officer | SELL | $25.86 | 5,000 | $129,300 | 615,650 | -0.8% |
| 2026-02-28 00:58 | 2026-02-25 | Ostergaard Torben | Officer - CEO Spinnaker | SELL | $30.44 | 600 | $18,266 | 46,094 | -1.3% |
| 2026-02-19 03:04 | 2026-02-17 | Ostergaard Torben | Officer - CEO Spinnaker | SELL | $28.57 | 6,105 | $174,391 | 46,694 | -11.6% |
| 2026-02-19 03:02 | 2025-11-14 | Zeltser Guy | Officer - Chief Financial Officer | BUY | $7.23 | 665 | $4,808 | 69,525 | +1.0% |
| 2026-02-12 00:52 | 2026-02-09 | McCathron Richard | Director, Officer - Chief Executive Officer | SELL | $29.14 | 5,000 | $145,700 | 442,704 | -1.1% |
| 2026-01-14 01:47 | 2026-01-09 | McCathron Richard | Director, Officer - Chief Executive Officer | SELL | $31.52 | 5,000 | $157,600 | 447,704 | -1.1% |
| 2025-12-29 20:20 | 2025-12-22 | Stienstra Michael | Officer - GM & Chief Insurance, HHIP | SELL | $31.12 | 3,900 | $121,366 | 71,281 | -5.2% |
| 2025-12-12 00:41 | 2025-12-09 | McCathron Richard | Director, Officer - Chief Executive Officer | SELL | $29.82 | 5,000 | $149,100 | 452,704 | -1.1% |
| 2025-11-26 00:24 | 2025-11-21 | Ostergaard Torben | Officer - CEO Spinnaker | SELL | $31.99 | 3,645 | $116,592 | 55,207 | -6.2% |
| 2025-11-20 00:56 | 2025-11-18 | Zeltser Guy | Officer - Chief Financial Officer | SELL | $32.16 | 1,819 | $58,494 | 68,860 | -2.6% |
| 2025-09-19 23:33 | 2025-09-17 | Zeltser Guy | Officer - Chief Financial Officer | SELL | $37.48 | 5,177 | $194,032 | 74,861 | -6.5% |
| 2025-09-11 01:04 | 2025-09-08 | McCathron Richard | Director, Officer - Chief Executive Officer | SELL | $34.12 | 2,725 | $92,969 | 470,388 | -0.6% |
| 2025-08-26 23:38 | 2025-08-22 | McCathron Richard | Director, Officer - Chief Executive Officer | SELL | $34.00 | 2,275 | $77,351 | 473,113 | -0.5% |
| 2025-07-03 13:02 | 2025-07-01 | Len FW Investor, LLC | Other | SELL | $28.17 | 514,309 | $14,488,085 | 2,476,418 | -17.2% |
| 2025-06-16 23:47 | 2025-06-12 | Ostergaard Torben | Officer - CEO Spinnaker | SELL | $29.95 | 2,444 | $73,198 | 64,349 | -3.7% |
| 2025-06-06 23:50 | 2025-06-04 | Ostergaard Torben | Officer - CEO Spinnaker | SELL | $24.61 | 4,889 | $120,317 | 66,793 | -6.8% |
| 2025-04-03 23:34 | 2025-04-01 | Wand Assaf | Director, Officer - Executive Chairman BoD | SELL | $25.04 | 12,250 | $306,701 | 474,564 | -2.5% |
| 2025-03-06 01:33 | 2025-03-03 | Wand Assaf | Director, Officer - Executive Chairman BoD | SELL | $28.90 | 12,250 | $354,045 | 486,814 | -2.5% |
| 2025-02-20 02:59 | 2025-02-18 | Stienstra Michael | Officer - GM & Chief Insurance, HHIP | SELL | $30.02 | 2,329 | $69,913 | 59,648 | -3.8% |
| 2025-02-07 01:14 | 2025-02-04 | Ostergaard Torben | Officer - CEO Spinnaker | SELL | $30.17 | 40,431 | $1,219,609 | 54,835 | -42.4% |
| 2025-02-06 00:33 | 2025-02-03 | Wand Assaf | Director, Officer - Executive Chairman BoD | SELL | $26.76 | 12,250 | $327,799 | 499,064 | -2.4% |
| 2025-02-01 01:06 | 2025-01-29 | Ostergaard Torben | Officer - CEO Spinnaker | SELL | $27.25 | 3,022 | $82,359 | 95,266 | -3.1% |
| 2025-01-11 00:16 | 2025-01-08 | Ostergaard Torben | Officer - CEO Spinnaker | SELL | $25.77 | 3,022 | $77,872 | 98,288 | -3.0% |
| 2025-01-04 02:01 | 2025-01-02 | Wand Assaf | Director, Officer - Executive Chairman BoD | SELL | $26.02 | 12,250 | $318,772 | 511,314 | -2.3% |
| 2025-01-04 01:59 | 2025-01-02 | Ellis Stewart | Officer - CFO/ Chief Strategy Officer | SELL | $26.34 | 10,000 | $263,416 | 318,215 | -3.0% |
| 2024-12-27 00:11 | 2024-12-23 | Ostergaard Torben | Officer - CEO Spinnaker | SELL | $25.91 | 3,022 | $78,297 | 101,310 | -2.9% |
| 2024-12-21 01:28 | 2024-12-18 | Ellis Stewart | Officer - CFO/ Chief Strategy Officer | SELL | $25.91 | 12,000 | $310,958 | 328,215 | -3.5% |
| 2024-12-20 02:34 | 2024-12-17 | Ostergaard Torben | Officer - CEO Spinnaker | SELL | $26.46 | 2,092 | $55,360 | 104,332 | -2.0% |
| 2024-12-05 00:40 | 2024-12-02 | Wand Assaf | Director, Officer - Executive Chairman BoD | SELL | $31.67 | 12,250 | $387,951 | 523,564 | -2.3% |
| 2024-11-26 03:41 | 2024-11-21 | McCathron Richard | Director, Officer - Chief Executive Officer | SELL | $30.16 | 15,000 | $452,432 | 339,623 | -4.2% |
| 2024-11-20 00:42 | 2024-11-18 | Stienstra Michael | Officer - GM & Chief Insurance, HHIP | SELL | $28.38 | 2,448 | $69,477 | 65,008 | -3.6% |
| 2024-11-13 00:51 | 2024-11-08 | Stienstra Michael | Officer - GM & Chief Insurance, HHIP | SELL | $25.55 | 855 | $21,845 | 70,249 | -1.2% |
| 2024-11-13 00:51 | 2024-11-08 | McCathron Richard | Director, Officer - Chief Executive Officer | SELL | $25.55 | 10,000 | $255,547 | 366,146 | -2.7% |
| 2024-11-09 01:21 | 2024-11-06 | Badia Anirudh | Officer - Chief Accounting Officer | SELL | $24.49 | 2,552 | $62,495 | 102,315 | -2.4% |
| 2024-11-06 00:32 | 2024-11-01 | Wand Assaf | Director, Officer - Executive Chairman BoD | SELL | $20.81 | 12,250 | $254,902 | 535,814 | -2.2% |
| 2024-10-03 23:39 | 2024-10-01 | Wand Assaf | Director, Officer - Executive Chairman BoD | SELL | $16.19 | 12,250 | $198,383 | 548,064 | -2.2% |
| 2024-08-15 04:20 | 2024-08-12 | Harry Yuval | Officer - Chief Revenue Officer | SELL | $18.49 | 18,925 | $349,912 | 104,247 | -15.4% |
| 2024-05-29 23:21 | 2024-05-24 | Harry Yuval | Officer - Chief Revenue Officer | SELL | $18.16 | 14,995 | $272,315 | 123,993 | -10.8% |
| 2024-05-17 00:42 | 2024-05-14 | Harry Yuval | Officer - Chief Revenue Officer | SELL | $18.51 | 1,192 | $22,064 | 143,149 | -0.8% |
| 2024-03-26 23:10 | 2024-03-22 | Harry Yuval | Officer - Chief Revenue Officer | OPT+S | $17.20 | 14,938 | $256,883 | 145,162 | 0.0% |
| 2024-03-14 00:19 | 2024-03-11 | Badia Anirudh | Officer - Chief Accounting Officer | SELL | $18.39 | 1,735 | $31,906 | 122,454 | -1.4% |
| 2023-08-22 00:30 | 2023-08-17 | NICHOLS JOHN DRAKE | Director | BUY | $10.72 | 29,573 | $317,014 | 50,000 | +144.8% |
| 2023-08-17 00:22 | 2023-08-14 | NICHOLS JOHN DRAKE | Director | BUY | $10.24 | 20,427 | $209,211 | 20,427 | +100.0% |
| 2023-03-21 03:46 | 2023-03-16 | Knauf Noah | Director | BUY | $14.43 | 208,531 | $3,008,685 | 208,531 | +100.0% |
| 2023-03-11 00:42 | 2023-03-09 | Landman Sam | Director | BUY | $12.89 | 1,985 | $25,587 | 7,563 | +35.6% |
| 2021-11-27 02:01 | 2021-11-24 | McCathron Richard | Director, Officer - President | BUY | $3.75 | 27,000 | $101,299 | 2,905,609 | +0.9% |
| 2021-11-24 01:05 | 2021-11-19 | Landman Sam | Director | BUY | $3.72 | 6,000 | $22,320 | 11,813 | +103.2% |
| 2021-11-24 01:03 | 2021-11-19 | Wand Assaf | Director, Officer - See Remarks | BUY | $3.70 | 40,650 | $150,588 | 17,151,793 | +0.2% |
| 2021-08-26 00:40 | 2021-08-23 | Wand Assaf | Director, Officer - See Remarks | BUY | $4.00 | 11,800 | $47,141 | 17,111,143 | +0.1% |
| 2021-08-24 01:46 | 2021-08-19 | Wand Assaf | Director, Officer - See Remarks | BUY | $4.31 | 11,395 | $49,155 | 17,099,343 | +0.1% |
How to Interpret $HIPO Trades
Not every insider transaction in Hippo Holdings Inc. is a signal for immediate action. Professional investors look for "cluster buying"—when multiple executives simultaneously purchase $HIPO shares on the open market. It is crucial to distinguish between scheduled sales (under Rule 10b5-1) and voluntary increases in ownership, which demonstrate management’s true conviction that the stock is undervalued.
Data Source & Accuracy for HIPO
Insider activity data for Hippo Holdings Inc. is streamed in real-time directly from the SEC EDGAR system. We analyze raw Form 4 filings, filtering out technical adjustments and complex derivative transactions. This provides a transparent view of how ownership structure is evolving in $HIPO, allowing you to follow the capital of those with the most intimate knowledge of the company.
UNDERSTANDING THE DATA
FILING DATE: The date and time when the transaction was reported to the SEC. This is when the public first receives the information.
TRADE DATE: The actual day the insider executed the purchase or sale in the market.
INDUSTRY: The specific market sector the company operates in. Useful for identifying broader institutional capital flows across sectors.
OWNED AFTER: The total number of shares held by the insider following the transaction. This highlights the insider's remaining conviction in the company.
CHANGE %: The percentage increase or decrease of the insider's total position. Large percentage changes often carry more weight than the dollar amount alone.
TRADE TYPES DEFINITIONS
BUY: An open market purchase. Typically indicates an insider's belief that the stock is undervalued or poised for growth.
SELL: An open market sale. While often used for diversification or liquidity, large or unexpected sales can be a warning signal.
OPT+S (OPTION EXERCISE & SALE): This occurs when an insider exercises their stock options and sells them immediately. Often part of a structured compensation plan.