HIPO
Hippo Holdings Inc
NYSE: HIPO · FINANCIAL SERVICES · INSURANCE - PROPERTY & CASUALTY
$26.71
-5.16% today
Updated 2026-06-03
Market cap
$646.21M
P/E ratio
5.64
P/S ratio
1.35x
EPS (TTM)
$4.40
Dividend yield
—
52W range
$24 – $39
Volume
0.1M
Hippo Holdings Inc (HIPO) Insider transactions
Net insider activity
Net selling (205,280 shares)
Buy transactions
31
Sell transactions
69
All transactions
| Date | Insider | Title | Type | Shares | Price | Value |
|---|---|---|---|---|---|---|
| 2026-05-15 | ZELTSER, GUY | Chief Financial Officer | Sale | 4,169 | $26.41 | $110112.88 |
| 2026-05-15 | STIENSTRA, MICHAEL | GM & Chief Insurance, HHIP | Sale | 1,259 | $26.41 | $33253.09 |
| 2026-05-15 | OSTERGAARD, TORBEN | CEO Spinnaker | Sale | 3,667 | $26.10 | $95706.13 |
| 2026-05-15 | OSTERGAARD, TORBEN | CEO Spinnaker | Sale | 1,340 | $26.41 | $35392.48 |
| 2026-05-15 | MCCATHRON, RICHARD | Director, Chief Executive Officer | Sale | 8,779 | $26.41 | $231873.58 |
| 2026-05-14 | ZELTSER, GUY | Chief Financial Officer | Buy | 743 | $22.72 | $16880.96 |
| 2026-05-11 | MCCATHRON, RICHARD | Director, Chief Executive Officer | Sale | 5,000 | $27.10 | $135500.00 |
| 2026-04-27 | ZELTSER, GUY | Chief Financial Officer | Sale | 1,091 | $28.21 | $30775.91 |
| 2026-04-27 | STIENSTRA, MICHAEL | GM & Chief Insurance, HHIP | Sale | 794 | $28.21 | $22397.87 |
| 2026-04-27 | OSTERGAARD, TORBEN | CEO Spinnaker | Sale | 1,438 | $28.21 | $40564.40 |
| 2026-04-27 | MCCATHRON, RICHARD | Director, Chief Executive Officer | Sale | 1,438 | $28.21 | $40564.40 |
| 2026-04-09 | MCCATHRON, RICHARD | Director, Chief Executive Officer | Sale | 5,000 | $26.05 | $130250.00 |
| 2026-03-09 | MCCATHRON, RICHARD | Director, Chief Executive Officer | Sale | 5,000 | $25.86 | $129300.00 |
| 2026-03-03 | MCCATHRON, RICHARD | Director, Chief Executive Officer | Buy | 113,719 | — | — |
| 2026-03-03 | MCCATHRON, RICHARD | Director, Chief Executive Officer | Buy | 75,813 | — | — |
| 2026-03-02 | ZELTSER, GUY | Chief Financial Officer | Buy | 37,024 | — | — |
| 2026-03-02 | ZELTSER, GUY | Chief Financial Officer | Buy | 24,683 | — | — |
| 2026-03-02 | STIENSTRA, MICHAEL | GM & Chief Insurance, HHIP | Buy | 14,810 | — | — |
| 2026-03-02 | STIENSTRA, MICHAEL | GM & Chief Insurance, HHIP | Buy | 9,874 | — | — |
| 2026-03-02 | OSTERGAARD, TORBEN | CEO Spinnaker | Buy | 14,810 | — | — |
| 2026-03-02 | OSTERGAARD, TORBEN | CEO Spinnaker | Buy | 9,874 | — | — |
| 2026-02-25 | OSTERGAARD, TORBEN | CEO Spinnaker | Sale | 600 | $30.44 | $18266.10 |
| 2026-02-17 | OSTERGAARD, TORBEN | CEO Spinnaker | Sale | 6,105 | $28.57 | $174391.16 |
| 2026-02-15 | ZELTSER, GUY | Chief Financial Officer | Sale | 4,483 | $28.59 | $128177.49 |
| 2026-02-15 | STIENSTRA, MICHAEL | GM & Chief Insurance, HHIP | Sale | 2,752 | $28.59 | $78684.91 |
| 2026-02-15 | OSTERGAARD, TORBEN | CEO Spinnaker | Sale | 2,408 | $28.59 | $68849.30 |
| 2026-02-15 | MCCATHRON, RICHARD | Director, Chief Executive Officer | Sale | 11,586 | $28.59 | $331265.75 |
| 2026-02-09 | MCCATHRON, RICHARD | Director, Chief Executive Officer | Sale | 5,000 | $29.14 | $145700.00 |
| 2026-01-09 | MCCATHRON, RICHARD | Director, Chief Executive Officer | Sale | 5,000 | $31.52 | $157600.00 |
| 2025-12-22 | STIENSTRA, MICHAEL | GM & Chief Insurance, HHIP | Sale | 3,900 | $31.12 | $121365.66 |
| 2025-12-18 | NICHOLS, JOHN DRAKE | Director | Sale | 4,935 | — | — |
| 2025-12-09 | MCCATHRON, RICHARD | Director, Chief Executive Officer | Sale | 5,000 | $29.82 | $149100.00 |
| 2025-11-21 | OSTERGAARD, TORBEN | CEO Spinnaker | Sale | 3,493 | $31.96 | $111631.74 |
| 2025-11-21 | OSTERGAARD, TORBEN | CEO Spinnaker | Sale | 152 | $32.63 | $4960.16 |
| 2025-11-18 | ZELTSER, GUY | Chief Financial Officer | Sale | 1,719 | $32.12 | $55219.61 |
| 2025-11-18 | ZELTSER, GUY | Chief Financial Officer | Sale | 100 | $32.74 | $3274.00 |
| 2025-11-15 | ZELTSER, GUY | Chief Financial Officer | Sale | 4,182 | $31.11 | $130117.49 |
| 2025-11-15 | STIENSTRA, MICHAEL | GM & Chief Insurance, HHIP | Sale | 2,463 | $31.11 | $76633.04 |
| 2025-11-15 | OSTERGAARD, TORBEN | CEO Spinnaker | Sale | 2,123 | $31.11 | $66054.39 |
| 2025-11-15 | MCCATHRON, RICHARD | Director, Chief Executive Officer | Sale | 11,326 | $31.11 | $352393.77 |
| 2025-11-14 | ZELTSER, GUY | Chief Financial Officer | Buy | 665 | $7.23 | $4807.95 |
| 2025-10-01 | HOLLIDAY, SUSAN CLAIRE | Director | Buy | 2,502 | — | — |
| 2025-10-01 | HAY, LAURA J | Director | Buy | 2,502 | — | — |
| 2025-09-17 | ZELTSER, GUY | Chief Financial Officer | Sale | 4,977 | $37.46 | $186422.99 |
| 2025-09-17 | ZELTSER, GUY | Chief Financial Officer | Sale | 200 | $38.05 | $7609.00 |
| 2025-09-10 | ZELTSER, GUY | Chief Financial Officer | Sale | 1,029 | $36.97 | $38042.13 |
| 2025-09-10 | STIENSTRA, MICHAEL | GM & Chief Insurance, HHIP | Sale | 752 | $36.97 | $27801.44 |
| 2025-09-10 | OSTERGAARD, TORBEN | CEO Spinnaker | Sale | 1,358 | $36.97 | $50205.26 |
| 2025-09-10 | MCCATHRON, RICHARD | Director, Chief Executive Officer | Sale | 1,358 | $36.97 | $50205.26 |
| 2025-09-08 | MCCATHRON, RICHARD | Director, Chief Executive Officer | Sale | 2,725 | $34.12 | $92969.37 |
| 2025-08-22 | MCCATHRON, RICHARD | Director, Chief Executive Officer | Sale | 2,275 | $34.00 | $77350.91 |
| 2025-08-15 | ZELTSER, GUY | Chief Financial Officer | Sale | 3,973 | $30.91 | $122805.43 |
| 2025-08-15 | STIENSTRA, MICHAEL | GM & Chief Insurance, HHIP | Sale | 2,341 | $30.91 | $72360.31 |
| 2025-08-15 | OSTERGAARD, TORBEN | CEO Spinnaker | Sale | 2,016 | $30.91 | $62314.56 |
| 2025-08-15 | MCCATHRON, RICHARD | Director, Chief Executive Officer | Sale | 10,759 | $30.91 | $332560.69 |
| 2025-07-01 | LEN, FW INVESTOR, LLC | Former 10% Owner | Sale | 514,309 | $28.17 | $14.49M |
| 2025-06-12 | OSTERGAARD, TORBEN | CEO Spinnaker | Sale | 2,444 | $29.95 | $73197.80 |
| 2025-06-04 | OSTERGAARD, TORBEN | CEO Spinnaker | Sale | 4,889 | $24.61 | $120316.82 |
| 2025-06-03 | WIJNBERG, SANDRA S | Director | Buy | 5,801 | $24.35 | $141254.35 |
| 2025-06-03 | WIJNBERG, SANDRA S | Director | Buy | 4,738 | — | — |
| 2025-06-03 | SCHAAF, MARK | Director | Buy | 5,801 | $24.35 | $141254.35 |
| 2025-06-03 | SCHAAF, MARK | Director | Buy | 4,738 | — | — |
| 2025-06-03 | NICHOLS, JOHN DRAKE | Director | Buy | 5,801 | $24.35 | $141254.35 |
| 2025-06-03 | NICHOLS, JOHN DRAKE | Director | Buy | 4,738 | — | — |
| 2025-06-03 | LANDMAN, SAM | Director | Buy | 5,801 | $24.35 | $141254.35 |
| 2025-06-03 | LANDMAN, SAM | Director | Buy | 4,738 | — | — |
| 2025-06-03 | FRATER, HUGH R | Director | Sale | 5,801 | $24.35 | $141254.35 |
| 2025-06-03 | FRATER, HUGH R | Director | Buy | 4,738 | — | — |
| 2025-06-03 | FOUCHE, LORI DICKERSON | Director | Buy | 5,801 | $24.35 | $141254.35 |
| 2025-06-03 | FOUCHE, LORI DICKERSON | Director | Buy | 4,738 | — | — |
| 2025-06-03 | FEDER, ERIC | Director | Buy | 5,801 | $24.35 | $141254.35 |
| 2025-06-03 | FEDER, ERIC | Director | Buy | 4,738 | — | — |
| 2025-05-15 | ZELTSER, GUY | Chief Financial Officier | Sale | 3,972 | $22.10 | $87781.20 |
| 2025-05-15 | STIENSTRA, MICHAEL | GM & Chief Insurance, HHIP | Sale | 2,876 | $22.10 | $63559.60 |
| 2025-05-15 | OSTERGAARD, TORBEN | CEO Spinnaker | Sale | 3,602 | $22.10 | $79604.20 |
| 2025-05-15 | MCCATHRON, RICHARD | Director, Chief Executive Officer | Sale | 10,760 | $22.10 | $237796.00 |
| 2025-05-14 | ZELTSER, GUY | Chief Financial Officier | Buy | 2,276 | $8.50 | $19346.00 |
| 2025-04-01 | WAND, ASSAF | Director, Executive Chairman BoD | Sale | 12,250 | $25.04 | $306700.80 |
| 2025-03-05 | MCCATHRON, RICHARD | Director, Chief Executive Officer | Buy | 112,651 | — | — |
| 2025-03-05 | MCCATHRON, RICHARD | Director, Chief Executive Officer | Buy | 56,326 | — | — |
| 2025-03-04 | STIENSTRA, MICHAEL | GM & Chief Insurance, HHIP | Buy | 23,965 | — | — |
| 2025-03-04 | OSTERGAARD, TORBEN | CEO Spinnaker | Buy | 23,965 | — | — |
| 2025-03-04 | ELLIS, STEWART | CFO/ Chief Strategy Officer | Buy | 42,794 | — | — |
| 2025-03-03 | WAND, ASSAF | Director, Executive Chairman BoD | Sale | 12,250 | $28.90 | $354044.60 |
| 2025-02-18 | STIENSTRA, MICHAEL | GM & Chief Insurance, HHIP | Sale | 2,329 | $30.02 | $69913.32 |
| 2025-02-15 | STIENSTRA, MICHAEL | GM & Chief Insurance, HHIP | Sale | 3,031 | $30.11 | $91263.41 |
| 2025-02-15 | OSTERGAARD, TORBEN | CEO Spinnaker | Sale | 3,516 | $30.11 | $105866.76 |
| 2025-02-15 | MCCATHRON, RICHARD | Director, Chief Executive Officer | Sale | 11,693 | $30.11 | $352076.23 |
| 2025-02-15 | ELLIS, STEWART | CFO/ Chief Strategy Officer | Sale | 14,464 | $30.11 | $435511.04 |
| 2025-02-05 | OSTERGAARD, TORBEN | CEO Spinnaker | Sale | 19,285 | $30.29 | $584173.51 |
| 2025-02-04 | OSTERGAARD, TORBEN | CEO Spinnaker | Sale | 21,146 | $30.05 | $635437.30 |
| 2025-02-03 | WAND, ASSAF | Director, Executive Chairman BoD | Sale | 8,048 | $26.52 | $213408.01 |
| 2025-02-03 | WAND, ASSAF | Director, Executive Chairman BoD | Sale | 4,202 | $27.22 | $114390.63 |
| 2025-01-29 | OSTERGAARD, TORBEN | CEO Spinnaker | Sale | 3,022 | $27.25 | $82358.87 |
| 2025-01-08 | OSTERGAARD, TORBEN | CEO Spinnaker | Sale | 3,022 | $25.77 | $77872.10 |
| 2025-01-02 | WAND, ASSAF | Director, Executive Chairman BoD | Sale | 8,496 | $25.81 | $219255.42 |
| 2025-01-02 | WAND, ASSAF | Director, Executive Chairman BoD | Sale | 3,754 | $26.51 | $99516.66 |
| 2025-01-02 | ELLIS, STEWART | CFO/ Chief Strategy Officer | Sale | 5,667 | $26.11 | $147974.44 |
| 2025-01-02 | ELLIS, STEWART | CFO/ Chief Strategy Officer | Sale | 4,333 | $26.64 | $115441.09 |
| 2024-12-23 | OSTERGAARD, TORBEN | CEO Spinnaker | Sale | 3,022 | $25.91 | $78297.30 |
Frequently asked questions
Are HIPO insiders buying or selling?
Over the transactions on record, HIPO insiders have been net sellers, with about $23.71M in stock sold across 69 sales, against 9 open-market purchases.
Does insider selling at HIPO mean the stock will fall?
Not by itself. Most executive selling is pre-scheduled through 10b5-1 plans filed months in advance, and insiders sell for diversification, taxes, and liquidity far more often than out of any view on the price. Insider buying is the stronger signal, especially when several insiders buy around the same time, because there is usually only one reason to put personal cash into the stock.
Which HIPO insiders are selling the most?
Recent selling is concentrated in a few names. LEN, FW INVESTOR, LLC accounts for the largest share on record, with about $14.49M sold. Selling by one or two individuals matters less than broad selling across the whole leadership team, which is the pattern worth watching.