There have been 50 recent insider transactions recorded for Hippo Holdings Inc. (HIPO), including 13 buys and 34 sells. Total insider buying was valued at $852.33K and total insider selling at $18.21M.
Notable insiders with recent activity include Mccathron Richard, Ostergaard Torben, Stienstra Michael. Insider transactions can provide insights into how company leadership views the stock's valuation and future prospects.
Insider Transactions — HIPO
| Date |
Name |
Role |
Transaction |
Shares |
Avg. Price |
Value |
Shares Owned |
| 2026-03-09 |
Mccathron Richard |
Chief Executive Officer |
Informative Sell |
5,000 |
$25.86 |
$129.3K |
615,650 |
| 2026-03-03 |
Mccathron Richard |
Chief Executive Officer |
RSU Award |
113,719 |
- |
- |
544,837 |
| 2026-03-02 |
Ostergaard Torben |
CEO Spinnaker |
RSU Award |
14,810 |
- |
- |
60,904 |
| 2026-03-02 |
Stienstra Michael |
GM & Chief Insurance, Hhip |
RSU Award |
14,810 |
- |
- |
83,339 |
| 2026-03-02 |
Zeltser Guy |
Chief Financial Officer |
RSU Award |
37,024 |
- |
- |
102,066 |
| 2026-02-25 |
Ostergaard Torben |
CEO Spinnaker |
Informative Sell |
600 |
$30.44 |
$18.27K |
46,094 |
| 2026-02-17 |
Ostergaard Torben |
CEO Spinnaker |
Informative Sell |
6,105 |
$28.57 |
$174.39K |
46,694 |
| 2026-02-15 |
Mccathron Richard |
Chief Executive Officer |
Tax Withholding of RSU |
11,586 |
$28.59 |
$331.27K |
431,118 |
| 2026-02-15 |
Ostergaard Torben |
CEO Spinnaker |
Tax Withholding of RSU |
2,408 |
$28.59 |
$68.85K |
52,799 |
| 2026-02-15 |
Stienstra Michael |
GM & Chief Insurance, Hhip |
Tax Withholding of RSU |
2,752 |
$28.59 |
$78.68K |
68,529 |
| 2026-02-15 |
Zeltser Guy |
Chief Financial Officer |
Tax Withholding of RSU |
4,483 |
$28.59 |
$128.18K |
65,042 |
| 2026-02-09 |
Mccathron Richard |
Chief Executive Officer |
Informative Sell |
5,000 |
$29.14 |
$145.7K |
442,704 |
| 2026-01-09 |
Mccathron Richard |
Chief Executive Officer |
Informative Sell |
5,000 |
$31.52 |
$157.6K |
447,704 |
| 2025-12-22 |
Stienstra Michael |
GM & Chief Insurance, Hhip |
Informative Sell |
3,900 |
$31.12 |
$121.37K |
71,281 |
| 2025-12-18 |
Nichols John Drake |
Director |
Gift (Given) |
4,935 |
- |
- |
16,563 |
| 2025-12-09 |
Mccathron Richard |
Chief Executive Officer |
Informative Sell |
5,000 |
$29.82 |
$149.1K |
452,704 |
| 2025-11-21 |
Ostergaard Torben |
CEO Spinnaker |
Informative Sell |
152 |
$32.63 |
$4.96K |
55,207 |
| 2025-11-18 |
Zeltser Guy |
Chief Financial Officer |
Informative Sell |
100 |
$32.74 |
$3.27K |
68,860 |
| 2025-11-15 |
Mccathron Richard |
Chief Executive Officer |
Tax Withholding of RSU |
11,326 |
$31.11 |
$352.39K |
457,704 |
| 2025-11-15 |
Ostergaard Torben |
CEO Spinnaker |
Tax Withholding of RSU |
2,123 |
$31.11 |
$66.05K |
58,852 |
| 2025-11-15 |
Stienstra Michael |
GM & Chief Insurance, Hhip |
Tax Withholding of RSU |
2,463 |
$31.11 |
$76.63K |
75,181 |
| 2025-11-15 |
Zeltser Guy |
Chief Financial Officer |
Tax Withholding of RSU |
4,182 |
$31.11 |
$130.12K |
70,679 |
| 2025-11-14 |
Zeltser Guy |
Chief Financial Officer |
Informative Buy |
665 |
$7.23 |
$4.81K |
69,525 |
| 2025-10-01 |
Hay Laura J |
Officer |
Unknown |
- |
- |
- |
- |
| 2025-10-01 |
Hay Laura J |
Director |
RSU Award |
2,502 |
- |
- |
2,502 |
| 2025-10-01 |
Holliday Susan Claire |
Officer |
Unknown |
- |
- |
- |
- |
| 2025-10-01 |
Holliday Susan Claire |
Director |
RSU Award |
2,502 |
- |
- |
2,502 |
| 2025-09-17 |
Zeltser Guy |
Chief Financial Officer |
Informative Sell |
200 |
$38.05 |
$7.61K |
74,861 |
| 2025-09-10 |
Mccathron Richard |
Chief Executive Officer |
Tax Withholding of RSU |
1,358 |
$36.97 |
$50.21K |
469,030 |
| 2025-09-10 |
Ostergaard Torben |
CEO Spinnaker |
Tax Withholding of RSU |
1,358 |
$36.97 |
$50.21K |
60,975 |
| 2025-09-10 |
Stienstra Michael |
GM & Chief Insurance, Hhip |
Tax Withholding of RSU |
752 |
$36.97 |
$27.8K |
77,644 |
| 2025-09-10 |
Zeltser Guy |
Chief Financial Officer |
Tax Withholding of RSU |
1,029 |
$36.97 |
$38.04K |
80,038 |
| 2025-09-08 |
Mccathron Richard |
Chief Executive Officer |
Informative Sell |
2,725 |
$34.12 |
$92.97K |
470,388 |
| 2025-08-22 |
Mccathron Richard |
Chief Executive Officer |
Informative Sell |
2,275 |
$34.00 |
$77.35K |
473,113 |
| 2025-08-15 |
Mccathron Richard |
Chief Executive Officer |
Tax Withholding of RSU |
10,759 |
$30.91 |
$332.56K |
475,388 |
| 2025-08-15 |
Ostergaard Torben |
CEO Spinnaker |
Tax Withholding of RSU |
2,016 |
$30.91 |
$62.31K |
62,333 |
| 2025-08-15 |
Stienstra Michael |
GM & Chief Insurance, Hhip |
Tax Withholding of RSU |
2,341 |
$30.91 |
$72.36K |
78,396 |
| 2025-08-15 |
Zeltser Guy |
Chief Financial Officer |
Tax Withholding of RSU |
3,973 |
$30.91 |
$122.81K |
81,067 |
| 2025-07-01 |
Len Fw Investor, Llc |
Other: Former 10% Owner |
Informative Sell |
514,309 |
$28.17 |
$14.49M |
2,476,418 |
| 2025-06-12 |
Ostergaard Torben |
CEO Spinnaker |
Informative Sell |
2,444 |
$29.95 |
$73.2K |
64,349 |
| 2025-06-04 |
Ostergaard Torben |
CEO Spinnaker |
Informative Sell |
4,889 |
$24.61 |
$120.32K |
66,793 |
| 2025-06-03 |
Frater Hugh R |
Director |
RSU Award (Return) |
5,801 |
$24.35 |
$141.25K |
17,077 |
| 2025-06-03 |
Wijnberg Sandra S |
Director |
RSU Award |
5,801 |
$24.35 |
$141.25K |
17,077 |
| 2025-06-03 |
Nichols John Drake |
Director |
RSU Award |
5,801 |
$24.35 |
$141.25K |
16,760 |
| 2025-06-03 |
Feder Eric |
Director |
RSU Award |
5,801 |
$24.35 |
$141.25K |
17,077 |
| 2025-06-03 |
Fouche Lori Dickerson |
Director |
RSU Award |
5,801 |
$24.35 |
$141.25K |
17,077 |
| 2025-06-03 |
Landman Sam |
Director |
RSU Award |
5,801 |
$24.35 |
$141.25K |
19,534 |
| 2025-06-03 |
Schaaf Mark |
Director |
RSU Award |
5,801 |
$24.35 |
$141.25K |
11,365 |
| 2025-05-15 |
Mccathron Richard |
Chief Executive Officer |
Tax Withholding of RSU |
10,760 |
$22.10 |
$237.8K |
486,147 |
| 2025-05-15 |
Ostergaard Torben |
CEO Spinnaker |
Tax Withholding of RSU |
3,602 |
$22.10 |
$79.6K |
71,682 |
■ Informative Buy/Sell — open market transaction (most significant)
■ Uninformative Buy — award, option exercise, conversion
■ Uninformative Sell — tax withholding, award vest sale
■ Neutral — gift, trust, expiry
