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| Date | Insider | Role | Type | Shares | Price | Value | Chg% | SEC |
|---|---|---|---|---|---|---|---|---|
| 2026-01-08 | Schlosser Mario | President of Technology & CTO | Sell | 23,038 | $17.65 | $406,620.70 | -6.2% | → |
| 2026-01-06 | Schlosser Mario | President of Technology & CTO | Sell | 76,962 | $17.01 | $1,309,123.62 | -18.0% | → |
| 2026-01-05 | Schlosser Mario | President of Technology & CTO | Sell | 234,861 | $15.28 | $3,587,707.58 | -24.8% | → |
| 2025-12-24 | Schlosser Mario | President of Technology & CTO | Sell | 38,835 | $15.00 | $582,525.00 | -8.1% | → |
| 2025-12-02 | Schlosser Mario | President of Technology & CTO | Sell | 23,965 | $16.59 | $397,579.35 | -4.8% | → |
| 2025-12-02 | Blackley Richard Scott | Chief Financial Officer | Sell | 25,135 | $16.59 | $416,989.65 | -1.8% | → |
| 2025-12-02 | Liang Janet | President, Oscar Insurance | Sell | 7,338 | $16.59 | $121,737.42 | -4.1% | → |
| 2025-12-02 | Baltrus Victoria | Chief Accounting Officer | Sell | 4,149 | $16.59 | $68,831.91 | -2.0% | → |
| 2025-12-02 | McAnaney Adam | Chief Legal Officer | Sell | 1,852 | $16.59 | $30,724.68 | -1.0% | → |
| 2025-11-12 | Schlosser Mario | President of Technology & CTO | Sale+OE | 391,482 | $15.21 | $5,954,764.14 | -28.1% | → |
| 2025-09-22 | Schlosser Mario | President of Technology & CTO | Sale+OE | 395,000 | $18.43 | $7,279,850.00 | -44.1% | → |
| 2025-05-12 | Robinson Elbert O. Jr. | - | Sell | 25,000 | $16.43 | $410,750.00 | -27.9% | → |
| 2024-12-06 | Blackley Richard Scott | Chief Financial Officer | Sale+OE | 29,939 | $16.16 | $483,667.84 | -1.6% | → |
| 2024-12-06 | Quane Alessandrea C. | EVP, Chief Insurance Officer | Sale+OE | 16,793 | $16.16 | $271,293.21 | -1.9% | → |
| 2024-12-02 | Blackley Richard Scott | Chief Financial Officer | Sale+OE | 25,279 | $18.08 | $456,978.49 | -1.4% | → |
| 2024-12-02 | Baltrus Victoria | Chief Accounting Officer | Sale+OE | 8,078 | $18.08 | $146,028.91 | -2.7% | → |
| 2024-12-02 | Bopitiya Ranmali | EVP & Chief Legal Officer | Sale+OE | 19,157 | $18.08 | $346,308.44 | -3.8% | → |
| 2024-12-02 | Quane Alessandrea C. | EVP, Chief Insurance Officer | Sale+OE | 26,895 | $18.08 | $486,191.09 | -3.1% | → |
| 2024-12-02 | Wolin Steven | Chief Operating Officer | Sale+OE | 19,580 | $18.08 | $353,955.33 | -8.7% | → |
| 2024-12-02 | Schlosser Mario | President of Technology & CTO | Sale+OE | 6,516 | $18.08 | $117,792.09 | -3.8% | → |
| 2024-11-21 | Thrive Partners VII Growth GP, LLC | - | Buy | 188,395 | $16.91 | $3,185,680.73 | +1.5% | → |
| 2024-11-21 | Kushner Joshua | Co-Founder and Vice Chairman | Buy | 188,395 | $16.91 | $3,185,680.73 | +1.5% | → |
| 2024-11-20 | Robinson Elbert O. Jr. | - | Sell | 25,000 | $17.05 | $426,250.00 | -21.8% | → |
| 2024-11-14 | Thrive Partners VII Growth GP, LLC | - | Buy | 344,522 | $15.80 | $5,444,343.41 | +2.9% | → |
| 2024-11-14 | Kushner Joshua | Co-Founder and Vice Chairman | Buy | 344,522 | $15.80 | $5,444,343.41 | +2.9% | → |
| 2024-11-13 | Kushner Joshua | Co-Founder and Vice Chairman | Buy | 1,055,478 | $13.67 | $14,429,982.48 | +6.9% | → |
| 2024-11-13 | Thrive Partners VII Growth GP, LLC | - | Buy | 1,055,478 | $13.67 | $14,429,982.48 | +6.9% | → |
| 2024-09-06 | Quane Alessandrea C. | EVP, Chief Insurance Officer | Sale+OE | 16,793 | $17.06 | $286,488.58 | -4.1% | → |
| 2024-09-06 | Blackley Richard Scott | Chief Financial Officer | Sale+OE | 29,957 | $17.06 | $511,066.42 | -3.4% | → |
| 2024-09-04 | Schlosser Mario | President of Technology & CTO | Sale+OE | 2,916 | $17.64 | $51,424.65 | -1.9% | → |
| 2024-09-04 | Blackley Richard Scott | Chief Financial Officer | Sale+OE | 28,257 | $17.85 | $504,387.45 | -3.3% | → |