OSCR Insider Transactions
375 retained open-market purchase and sale rows from SEC Forms 3, 4 and 5, newest first. This page shows rows 1–100; provenance stays internal.
OSCR insiders transaction timeline
PurchaseSale
| Insider profile | Role | Date | Transaction | Shares | Price |
|---|---|---|---|---|---|
| Blackley Richard Scott | Chief Financial Officer | 2026-08-18 | Sale | 18,750 | $31.74 |
| Schlosser Mario | Director | 2026-07-01 | Sale | 30,228 | $31.65 |
| Schlosser Mario | Director | 2026-07-01 | Sale | 13,672 | $30.80 |
| Schlosser Mario | Director | 2026-07-01 | Sale | 3,600 | $29.50 |
| Bertolini Mark T | Chief Executive Officer | 2026-06-30 | Sale | 135,590 | $28.97 |
| Bertolini Mark T | Chief Executive Officer | 2026-06-30 | Sale | 488,654 | $28.35 |
| Bertolini Mark T | Chief Executive Officer | 2026-06-29 | Sale | 58,926 | $30.08 |
| Bertolini Mark T | Chief Executive Officer | 2026-06-29 | Sale | 555,826 | $29.17 |
| Bertolini Mark T | Chief Executive Officer | 2026-06-26 | Sale | 149,795.0 | $29.79 |
| Bertolini Mark T | Chief Executive Officer | 2026-06-26 | Sale | 441,373.0 | $29.11 |
| Bertolini Mark T | Chief Executive Officer | 2026-06-25 | Sale | 17,200.0 | $29.08 |
| Bertolini Mark T | Chief Executive Officer | 2026-06-25 | Sale | 597,942.0 | $28.6 |
| Schlosser Mario | Director | 2026-06-23 | Sale | 97.0 | $30.09 |
| Schlosser Mario | Director | 2026-06-23 | Sale | 31,912.0 | $29.58 |
| Schlosser Mario | Director | 2026-06-23 | Sale | 15,491.0 | $28.95 |
| Schlosser Mario | Director | 2026-06-23 | Sale | 102.0 | $30.09 |
| Schlosser Mario | Director | 2026-06-23 | Sale | 33,592.0 | $29.58 |
| Schlosser Mario | Director | 2026-06-23 | Sale | 16,306.0 | $28.95 |
| Schlosser Mario | Director | 2026-06-23 | Sale | 102.0 | $30.09 |
| Schlosser Mario | Director | 2026-06-23 | Sale | 33,591.0 | $29.58 |
| Schlosser Mario | Director | 2026-06-23 | Sale | 16,307.0 | $28.95 |
| Schlosser Mario | Director | 2026-06-23 | Sale | 1,799.0 | $30.09 |
| Schlosser Mario | Director | 2026-06-23 | Sale | 591,213.0 | $29.58 |
| Schlosser Mario | Director | 2026-06-23 | Sale | 286,988.0 | $28.95 |
| Baltrus Victoria | Chief Accounting Officer | 2026-06-02 | Sale | 432.0 | $22.45 |
| Baltrus Victoria | Chief Accounting Officer | 2026-06-02 | Sale | 1,091.0 | $21.74 |
| Liang Janet | President, Oscar Insurance | 2026-06-02 | Sale | 3,535.0 | $22.45 |
| Liang Janet | President, Oscar Insurance | 2026-06-02 | Sale | 8,940.0 | $21.74 |
| Schlosser Mario | Director | 2026-06-02 | Sale | 9,668.0 | $22.45 |
| Schlosser Mario | Director | 2026-06-02 | Sale | 24,452.0 | $21.74 |
| McAnaney Adam | Chief Legal Officer | 2026-06-02 | Sale | 2,794.0 | $22.45 |
| McAnaney Adam | Chief Legal Officer | 2026-06-02 | Sale | 7,065.0 | $21.74 |
| Blackley Richard Scott | Chief Financial Officer | 2026-06-02 | Sale | 8,977.0 | $22.45 |
| Blackley Richard Scott | Chief Financial Officer | 2026-06-02 | Sale | 22,706.0 | $21.74 |
| Blackley Richard Scott | Chief Financial Officer | 2026-05-18 | Sale | 110,000.0 | $25.03 |
| Blackley Richard Scott | Chief Financial Officer | 2026-05-14 | Sale | 8,741.0 | $23.79 |
| Blackley Richard Scott | Chief Financial Officer | 2026-05-14 | Sale | 91,259.0 | $23.1 |
| Bertolini Mark T | Chief Executive Officer | 2026-04-06 | Purchase | 1,000,000.0 | $11.92 |
| Liang Janet | President, Oscar Insurance | 2026-03-02 | Sale | 7,453.0 | $13.39 |
| Baltrus Victoria | Chief Accounting Officer | 2026-03-02 | Sale | 4,638.0 | $13.39 |
| McAnaney Adam | Chief Legal Officer | 2026-03-02 | Sale | 18,710.0 | $13.39 |
| Schlosser Mario | President of Technology & CTO | 2026-03-02 | Sale | 24,335.0 | $13.39 |
| Blackley Richard Scott | Chief Financial Officer | 2026-03-02 | Sale | 19,221.0 | $13.39 |
| Schlosser Mario | President of Technology & CTO | 2026-01-08 | Sale | 23,038.0 | $17.65 |
| Schlosser Mario | President of Technology & CTO | 2026-01-06 | Sale | 76,962.0 | $17.01 |
| Schlosser Mario | President of Technology & CTO | 2026-01-05 | Sale | 96,928.0 | $15.64 |
| Schlosser Mario | President of Technology & CTO | 2026-01-02 | Sale | 137,933.0 | $15.02 |
| Schlosser Mario | President of Technology & CTO | 2025-12-24 | Sale | 38,835.0 | $15.0 |
| Baltrus Victoria | Chief Accounting Officer | 2025-12-02 | Sale | 4,149.0 | $16.59 |
| Liang Janet | President, Oscar Insurance | 2025-12-02 | Sale | 7,338.0 | $16.59 |
| Schlosser Mario | President of Technology & CTO | 2025-12-02 | Sale | 23,965.0 | $16.59 |
| McAnaney Adam | Chief Legal Officer | 2025-12-02 | Sale | 1,852.0 | $16.59 |
| Blackley Richard Scott | Chief Financial Officer | 2025-12-02 | Sale | 25,135.0 | $16.59 |
| Schlosser Mario | President of Technology & CTO | 2025-11-12 | Sale | 105,300.0 | $15.05 |
| Schlosser Mario | President of Technology & CTO | 2025-11-11 | Sale | 286,182.0 | $15.27 |
| Schlosser Mario | President of Technology & CTO | 2025-09-22 | Sale | 395,000.0 | $18.43 |
| Robinson Elbert O. Jr. | Director | 2025-05-12 | Sale | 25,000.0 | $16.43 |
| Quane Alessandrea C. | EVP, Chief Insurance Officer | 2024-12-06 | Sale | 6,408.0 | $16.52 |
| Quane Alessandrea C. | EVP, Chief Insurance Officer | 2024-12-06 | Sale | 10,385.0 | $15.93 |
| Blackley Richard Scott | Chief Financial Officer | 2024-12-06 | Sale | 11,423.0 | $16.52 |
| Blackley Richard Scott | Chief Financial Officer | 2024-12-06 | Sale | 18,516.0 | $15.93 |
| Wolin Steven | Chief Operating Officer | 2024-12-02 | Sale | 353.0 | $18.48 |
| Wolin Steven | Chief Operating Officer | 2024-12-02 | Sale | 19,227.0 | $18.07 |
| Schlosser Mario | President of Technology & CTO | 2024-12-02 | Sale | 117.0 | $18.48 |
| Schlosser Mario | President of Technology & CTO | 2024-12-02 | Sale | 6,399.0 | $18.07 |
| Bopitiya Ranmali | EVP & Chief Legal Officer | 2024-12-02 | Sale | 345.0 | $18.48 |
| Bopitiya Ranmali | EVP & Chief Legal Officer | 2024-12-02 | Sale | 18,812.0 | $18.07 |
| Quane Alessandrea C. | EVP, Chief Insurance Officer | 2024-12-02 | Sale | 484.0 | $18.48 |
| Quane Alessandrea C. | EVP, Chief Insurance Officer | 2024-12-02 | Sale | 26,411.0 | $18.07 |
| Blackley Richard Scott | Chief Financial Officer | 2024-12-02 | Sale | 456.0 | $18.48 |
| Blackley Richard Scott | Chief Financial Officer | 2024-12-02 | Sale | 24,823.0 | $18.07 |
| Baltrus Victoria | Chief Accounting Officer | 2024-12-02 | Sale | 145.0 | $18.48 |
| Baltrus Victoria | Chief Accounting Officer | 2024-12-02 | Sale | 7,933.0 | $18.07 |
| Thrive Capital Partners VII Growth, L.P. | Director,TenPercentOwner | 2024-11-21 | Purchase | 100,000.0 | $16.86 |
| Claremount VII Associates, L.P. | Director,TenPercentOwner | 2024-11-21 | Purchase | 100,000.0 | $16.86 |
| Thrive Partners VII GP, LLC | Director,TenPercentOwner | 2024-11-21 | Purchase | 100,000.0 | $16.86 |
| Thrive Partners VII Growth GP, LLC | Director,TenPercentOwner | 2024-11-21 | Purchase | 100,000.0 | $16.86 |
| Kushner Joshua | Co-Founder and Vice Chairman | 2024-11-21 | Purchase | 100,000.0 | $16.86 |
| Robinson Elbert O. Jr. | Director | 2024-11-20 | Sale | 25,000.0 | $17.05 |
| Thrive Capital Partners VII Growth, L.P. | Director,TenPercentOwner | 2024-11-20 | Purchase | 88,395.0 | $16.97 |
| Claremount VII Associates, L.P. | Director,TenPercentOwner | 2024-11-20 | Purchase | 88,395.0 | $16.97 |
| Thrive Partners VII GP, LLC | Director,TenPercentOwner | 2024-11-20 | Purchase | 88,395.0 | $16.97 |
| Thrive Partners VII Growth GP, LLC | Director,TenPercentOwner | 2024-11-20 | Purchase | 88,395.0 | $16.97 |
| Kushner Joshua | Co-Founder and Vice Chairman | 2024-11-20 | Purchase | 88,395.0 | $16.97 |
| Thrive Capital Partners VII Growth, L.P. | Director,TenPercentOwner | 2024-11-14 | Purchase | 185,790.0 | $15.97 |
| Claremount VII Associates, L.P. | Director,TenPercentOwner | 2024-11-14 | Purchase | 185,790.0 | $15.97 |
| Thrive Partners VII GP, LLC | Director,TenPercentOwner | 2024-11-14 | Purchase | 185,790.0 | $15.97 |
| Thrive Partners VII Growth GP, LLC | Director,TenPercentOwner | 2024-11-14 | Purchase | 185,790.0 | $15.97 |
| Thrive Capital Partners VII Growth, L.P. | Director,TenPercentOwner | 2024-11-14 | Purchase | 158,732.0 | $15.61 |
| Claremount VII Associates, L.P. | Director,TenPercentOwner | 2024-11-14 | Purchase | 158,732.0 | $15.61 |
| Thrive Partners VII GP, LLC | Director,TenPercentOwner | 2024-11-14 | Purchase | 158,732.0 | $15.61 |
| Thrive Partners VII Growth GP, LLC | Director,TenPercentOwner | 2024-11-14 | Purchase | 158,732.0 | $15.61 |
| Kushner Joshua | Co-Founder and Vice Chairman | 2024-11-14 | Purchase | 185,790.0 | $15.97 |
| Kushner Joshua | Co-Founder and Vice Chairman | 2024-11-14 | Purchase | 158,732.0 | $15.61 |
| Kushner Joshua | Co-Founder and Vice Chairman | 2024-11-13 | Purchase | 358,619.0 | $13.74 |
| Thrive Capital Partners VII Growth, L.P. | Director,TenPercentOwner | 2024-11-13 | Purchase | 358,619.0 | $13.74 |
| Claremount VII Associates, L.P. | Director,TenPercentOwner | 2024-11-13 | Purchase | 358,619.0 | $13.74 |
| Thrive Partners VII GP, LLC | Director,TenPercentOwner | 2024-11-13 | Purchase | 358,619.0 | $13.74 |
| Thrive Partners VII Growth GP, LLC | Director,TenPercentOwner | 2024-11-13 | Purchase | 358,619.0 | $13.74 |
| Kushner Joshua | Co-Founder and Vice Chairman | 2024-11-12 | Purchase | 420,819.0 | $13.68 |