As of the latest Form 4 filed Jun 12, 2026.
What Hippo Holdings Inc insiders — officers, directors and 10% owners — have bought and sold in their own stock, straight from their SEC Form 4 filings. Values are shares × the reported transaction price where both are disclosed.
Buys plotted up, sells down; bar height is the disclosed dollar value (shares × reported price). Our Form 4 history is only complete from mid-2026, so early months are sparse — the series fills in as more filings land. Open-market purchases and sales only.
Newest filing first — the 49 most recent filings for HIPO.
| Filed | Trade date | Insider | Transaction | Shares | Price | Value | 10b5-1 | Filing |
|---|---|---|---|---|---|---|---|---|
| 2026-06-12 | 2026-06-10 | Boettcher Laura Chief Operating Officer | AAward | +11.7K | $0.00 | $0.00 | No | Form 4 ↗ |
| 2026-06-11 | 2026-06-09 | McCathron Richard Chief Executive Officer | SSale | −5.00K | $25.00 | $125K | Yes (planned) | Form 4 ↗ |
| 2026-06-05 | 2026-06-03 | Ellis Stewart Director | AAward | +4.82K | $0.00 | $0.00 | No | Form 4 ↗ |
| 2026-06-04 | 2026-06-02 | Holliday Susan Claire Director | AAward | +4.81K | $0.00 | $0.00 | No | Form 4 ↗ |
| 2026-06-04 | 2026-06-02 | Holliday Susan Claire, Director | AAward | +2.50K | $25.40 | $63.6K | No | Form 4 ↗ |
| 2026-06-04 | 2026-06-02 | Hay Laura J Director | AAward | +4.81K | $0.00 | $0.00 | No | Form 4 ↗ |
| 2026-06-04 | 2026-06-02 | Hay Laura J, Director | AAward | +2.50K | $25.40 | $63.6K | No | Form 4 ↗ |
| 2026-06-04 | 2026-06-02 | Schaaf Mark Director | AAward | +4.81K | $0.00 | $0.00 | No | Form 4 ↗ |
| 2026-06-04 | 2026-06-02 | Schaaf Mark, Director | AAward | +4.74K | $25.40 | $120K | No | Form 4 ↗ |
| 2026-06-04 | 2026-06-02 | Landman Sam Director | AAward | +4.81K | $0.00 | $0.00 | No | Form 4 ↗ |
| 2026-06-04 | 2026-06-02 | Landman Sam, Director | AAward | +4.74K | $25.40 | $120K | No | Form 4 ↗ |
| 2026-06-04 | 2026-06-02 | Fouche Lori Dickerson Director | AAward | +4.81K | $0.00 | $0.00 | No | Form 4 ↗ |
| 2026-06-04 | 2026-06-02 | Fouche Lori Dickerson, Director | AAward | +4.74K | $25.40 | $120K | No | Form 4 ↗ |
| 2026-06-04 | 2026-06-02 | Feder Eric Director | AAward | +4.74K | $25.40 | $120K | No | Form 4 ↗ |
| 2026-06-04 | 2026-06-02 | NICHOLS JOHN DRAKE Director | AAward | +4.81K | $0.00 | $0.00 | No | Form 4 ↗ |
| 2026-06-04 | 2026-06-02 | NICHOLS JOHN DRAKE, Director | AAward | +4.74K | $25.40 | $120K | No | Form 4 ↗ |
| 2026-06-04 | 2026-06-02 | WIJNBERG SANDRA S Director | AAward | +4.81K | $0.00 | $0.00 | No | Form 4 ↗ |
| 2026-06-04 | 2026-06-02 | WIJNBERG SANDRA S, Director | AAward | +4.74K | $25.40 | $120K | No | Form 4 ↗ |
| 2026-06-04 | 2026-06-02 | FRATER HUGH R Director | AAward | +4.81K | $0.00 | $0.00 | No | Form 4 ↗ |
| 2026-06-04 | 2026-06-02 | FRATER HUGH R, Director | AAward | +4.74K | $25.40 | $120K | No | Form 4 ↗ |
| 2026-05-19 | 2026-05-15 | Zeltser Guy Chief Financial Officer | FTax | −4.17K | $26.41 | $110K | No | Form 4 ↗ |
| 2026-05-19 | 2026-05-15 | Stienstra Michael GM & Chief Insurance, HHIP | FTax | −1.26K | $26.41 | $33.3K | No | Form 4 ↗ |
| 2026-05-19 | 2026-05-15 | Ostergaard Torben CEO Spinnaker | FTax | −1.34K | $26.41 | $35.4K | Yes (planned) | Form 4 ↗ |
| 2026-05-19 | 2026-05-15 | Ostergaard Torben, CEO Spinnaker | SSale | −3.67K | $26.10 | $95.7K | Yes (planned) | Form 4 ↗ |
| 2026-05-19 | 2026-05-15 | McCathron Richard Chief Executive Officer | FTax | −8.78K | $26.41 | $232K | No | Form 4 ↗ |
| 2026-05-19 | 2026-05-14 | Zeltser Guy Chief Financial Officer | AAward | +743.00 | $22.72 | $16.9K | No | Form 4 ↗ |
| 2026-05-13 | 2026-05-11 | McCathron Richard Chief Executive Officer | SSale | −5.00K | $27.10 | $136K | Yes (planned) | Form 4 ↗ |
| 2026-04-29 | 2026-04-27 | Zeltser Guy Chief Financial Officer | FTax | −1.09K | $28.21 | $30.8K | No | Form 4 ↗ |
| 2026-04-29 | 2026-04-27 | Stienstra Michael GM & Chief Insurance, HHIP | FTax | −794.00 | $28.21 | $22.4K | No | Form 4 ↗ |
| 2026-04-29 | 2026-04-27 | Ostergaard Torben CEO Spinnaker | FTax | −1.44K | $28.21 | $40.6K | No | Form 4 ↗ |
| 2026-04-29 | 2026-04-27 | McCathron Richard Chief Executive Officer | FTax | −1.44K | $28.21 | $40.6K | No | Form 4 ↗ |
| 2026-04-13 | 2026-04-09 | McCathron Richard Chief Executive Officer | SSale | −5.00K | $26.05 | $130K | Yes (planned) | Form 4 ↗ |
| 2026-03-11 | 2026-03-09 | McCathron Richard Chief Executive Officer | SSale | −5.00K | $25.86 | $129K | Yes (planned) | Form 4 ↗ |
| 2026-03-05 | 2026-03-03 | McCathron Richard Chief Executive Officer | AAward | +75.8K | $0.00 | $0.00 | No | Form 4 ↗ |
| 2026-03-05 | 2026-03-03 | McCathron Richard, Chief Executive Officer | AAward | +114K | $0.00 | $0.00 | No | Form 4 ↗ |
| 2026-03-05 | 2026-03-02 | Zeltser Guy Chief Financial Officer | AAward | +24.7K | $0.00 | $0.00 | No | Form 4 ↗ |
| 2026-03-05 | 2026-03-02 | Zeltser Guy, Chief Financial Officer | AAward | +37.0K | $0.00 | $0.00 | No | Form 4 ↗ |
| 2026-03-05 | 2026-03-02 | Stienstra Michael GM & Chief Insurance, HHIP | AAward | +9.87K | $0.00 | $0.00 | No | Form 4 ↗ |
| 2026-03-05 | 2026-03-02 | Stienstra Michael, GM & Chief Insurance, HHIP | AAward | +14.8K | $0.00 | $0.00 | No | Form 4 ↗ |
| 2026-03-05 | 2026-03-02 | Ostergaard Torben CEO Spinnaker | AAward | +9.87K | $0.00 | $0.00 | No | Form 4 ↗ |
| 2026-03-05 | 2026-03-02 | Ostergaard Torben, CEO Spinnaker | AAward | +14.8K | $0.00 | $0.00 | No | Form 4 ↗ |
| 2026-02-27 | 2026-02-25 | Ostergaard Torben CEO Spinnaker | SSale | −600.00 | $30.44 | $18.3K | Yes (planned) | Form 4 ↗ |
| 2026-02-11 | 2026-02-09 | McCathron Richard Chief Executive Officer | SSale | −5.00K | $29.14 | $146K | Yes (planned) | Form 4 ↗ |
| 2024-05-03 | 2024-05-01 | Badia Anirudh Chief Accounting Officer | FTax | −482.00 | $21.97 | $10.6K | No | Form 4 ↗ |
| 2024-05-03 | 2024-05-01 | Ostergaard Torben CEO Spinnaker | FTax | −906.00 | $21.97 | $19.9K | No | Form 4 ↗ |
| 2024-05-03 | 2024-05-01 | Stienstra Michael GM & Chief Insurance, HHIP | FTax | −495.00 | $21.97 | $10.9K | No | Form 4 ↗ |
| 2024-05-03 | 2024-05-01 | Ellis Stewart CFO/ Chief Strategy Officer | FTax | −1.17K | $21.97 | $25.6K | No | Form 4 ↗ |
| 2024-05-03 | 2024-05-01 | Harry Yuval Chief Revenue Officer | FTax | −821.00 | $21.97 | $18.0K | No | Form 4 ↗ |
| 2024-05-03 | 2024-05-01 | McCathron Richard Chief Executive Officer | FTax | −906.00 | $21.97 | $19.9K | No | Form 4 ↗ |
Insiders — a company’s officers, directors and holders of more than 10% of its stock — must report any trade in that stock to the SEC on a Form 4 within two business days. Each row here is one transaction from those filings.
The transaction code tells you what happened: Purchase (P) and Sale (S) are open-market trades — the ones markets watch most; Award (A) is a granted stock or unit, Option exercise (M) converts options into shares, and Gift (G) is a transfer for no consideration. Awards, exercises and gifts are largely compensation or administrative, not a directional bet.
One caveat on sales: many are made under a Rule 10b5-1 plan scheduled months in advance, so a sale is not automatically a bearish signal. Insider activity is a noisy input — read it alongside the filings, not on its own.
See also HIPO’s full analysis or the market-wide insider trading feed. The tabs above jump to HIPO’s other SEC data.
Source: SEC Form 4 filings for HIPO, parsed from EDGAR. Transaction prices are as reported in the filing — SEC public-domain data, not market quotes. Values are shares × reported price where both are disclosed; grants and gifts often carry no price. A delayed record of what insiders reported, not a live position or a recommendation.
Research and education only — not financial advice. TENKis not a registered investment adviser or broker-dealer and gives no personalized advice. Every call is impersonal — identical for all users, generated on a schedule from SEC filings plus a delayed/third-party price feed — may be wrong or out of date, and is not a recommendation to buy or sell any security. The operator and an affiliated trading operation may hold or trade the securities TENK rates; see Disclosures. Past performance does not guarantee future results. Do your own research.