The public view is the crawlable proof. The same sourced dataset is available through REST and MCP for agents, research scripts, and back-office tools.
| Date | Insider | Role | Action | Shares | Price | Value |
|---|---|---|---|---|---|---|
| Jul 9, 2026 | Plouffe David | Director | Grant(A) | 681 | $31.20 | $21K |
| Jul 9, 2026 | Gassen William | Director | Grant(A) | 684 | $31.20 | $21K |
| Jul 9, 2026 | Sankaran Sid | Director | Grant(A) | 858 | $31.20 | $27K |
| Jul 1, 2026 | Schlosser Mario | Director | Conversion(C) | 48K | — | — |
| Jul 1, 2026 | Schlosser Mario | Director | Sell(S) | 4K | $29.50 | $106K |
| Jul 1, 2026 | Schlosser Mario | Director | Sell(S) | 14K | $30.80 | $421K |
| Jul 1, 2026 | Schlosser Mario | Director | Sell(S) | 30K | $31.65 | $957K |
| Jul 1, 2026 | Schlosser Mario | Director | Conversion(C) | 48K | — | $0 |
| Jun 30, 2026 | Bertolini Mark T | Chief Executive Officer, Director | Sell(S) | 489K | $28.35 | $13.9M |
| Jun 30, 2026 | Bertolini Mark T | Chief Executive Officer, Director | Sell(S) | 136K | $28.97 | $3.9M |
| Jun 29, 2026 | Bertolini Mark T | Chief Executive Officer, Director | Sell(S) | 556K | $29.17 | $16.2M |
| Jun 29, 2026 | Bertolini Mark T | Chief Executive Officer, Director | Sell(S) | 59K | $30.08 | $1.8M |
| Jun 26, 2026 | Bertolini Mark T | Chief Executive Officer, Director | Sell(S) | 441K | $29.11 | $12.8M |
| Jun 26, 2026 | Bertolini Mark T | Chief Executive Officer, Director | Sell(S) | 150K | $29.79 | $4.5M |
| Jun 25, 2026 | Bertolini Mark T | Chief Executive Officer, Director | Sell(S) | 598K | $28.60 | $17.1M |
| Jun 25, 2026 | Bertolini Mark T | Chief Executive Officer, Director | Sell(S) | 17K | $29.08 | $500K |
| Jun 23, 2026 | Schlosser Mario | Director | Conversion(C) | 880K | — | — |
| Jun 23, 2026 | Schlosser Mario | Director | Sell(S) | 287K | $28.95 | $8.3M |
| Jun 23, 2026 | Schlosser Mario | Director | Sell(S) | 591K | $29.58 | $17.5M |
| Jun 23, 2026 | Schlosser Mario | Director | Sell(S) | 2K | $30.09 | $54K |
| Jun 23, 2026 | Schlosser Mario | Director | Conversion(C) | 50K | — | — |
| Jun 23, 2026 | Schlosser Mario | Director | Sell(S) | 16K | $28.95 | $472K |
| Jun 23, 2026 | Schlosser Mario | Director | Sell(S) | 34K | $29.58 | $994K |
| Jun 23, 2026 | Schlosser Mario | Director | Sell(S) | 102 | $30.09 | $3K |
| Jun 23, 2026 | Schlosser Mario | Director | Conversion(C) | 50K | — | — |
| Jun 23, 2026 | Schlosser Mario | Director | Sell(S) | 16K | $28.95 | $472K |
| Jun 23, 2026 | Schlosser Mario | Director | Sell(S) | 34K | $29.58 | $994K |
| Jun 23, 2026 | Schlosser Mario | Director | Sell(S) | 102 | $30.09 | $3K |
| Jun 23, 2026 | Schlosser Mario | Director | Conversion(C) | 48K | — | — |
| Jun 23, 2026 | Schlosser Mario | Director | Sell(S) | 15K | $28.95 | $448K |
| Jun 23, 2026 | Schlosser Mario | Director | Sell(S) | 32K | $29.58 | $944K |
| Jun 23, 2026 | Schlosser Mario | Director | Sell(S) | 97 | $30.09 | $3K |
| Jun 23, 2026 | Schlosser Mario | Director | Option exercise(M) | 660K | — | $0 |
| Jun 23, 2026 | Schlosser Mario | Director | Option exercise(M) | 660K | $9.75 | $6.4M |
| Jun 23, 2026 | Schlosser Mario | Director | Conversion(C) | 880K | — | $0 |
| Jun 23, 2026 | Schlosser Mario | Director | Conversion(C) | 50K | — | $0 |
| Jun 23, 2026 | Schlosser Mario | Director | Conversion(C) | 50K | — | $0 |
| Jun 23, 2026 | Schlosser Mario | Director | Conversion(C) | 48K | — | $0 |
| Jun 4, 2026 | Lang Laura W | Director | Grant(A) | 8K | — | $0 |
| Jun 4, 2026 | Gassen William | Director | Grant(A) | 8K | — | $0 |
| Jun 4, 2026 | Plouffe David | Director | Grant(A) | 8K | — | $0 |
| Jun 4, 2026 | Sankaran Sid | Director | Grant(A) | 8K | — | $0 |
| Jun 4, 2026 | Wittman Vanessa Ames | Director | Grant(A) | 8K | — | $0 |
| Jun 2, 2026 | Baltrus Victoria | Chief Accounting Officer | Sell(S) | 1K | $21.74 | $24K |
| Jun 2, 2026 | Baltrus Victoria | Chief Accounting Officer | Sell(S) | 432 | $22.45 | $10K |
| Jun 2, 2026 | Schlosser Mario | Director | Sell(S) | 24K | $21.74 | $532K |
| Jun 2, 2026 | Schlosser Mario | Director | Sell(S) | 10K | $22.45 | $217K |
| Jun 2, 2026 | McAnaney Adam | Chief Legal Officer | Sell(S) | 7K | $21.74 | $154K |
| Jun 2, 2026 | McAnaney Adam | Chief Legal Officer | Sell(S) | 3K | $22.45 | $63K |
| Jun 2, 2026 | Liang Janet | President, Oscar Insurance | Sell(S) | 9K | $21.74 | $194K |
| Jun 2, 2026 | Liang Janet | President, Oscar Insurance | Sell(S) | 4K | $22.45 | $79K |
| Jun 2, 2026 | Blackley Richard Scott | Chief Financial Officer | Sell(S) | 23K | $21.74 | $494K |
| Jun 2, 2026 | Blackley Richard Scott | Chief Financial Officer | Sell(S) | 9K | $22.45 | $202K |
| May 18, 2026 | Blackley Richard Scott | Chief Financial Officer | Sell(S) | 110K | $25.03 | $2.8M |
| May 14, 2026 | Blackley Richard Scott | Chief Financial Officer | Sell(S) | 91K | $23.10 | $2.1M |
| May 14, 2026 | Blackley Richard Scott | Chief Financial Officer | Sell(S) | 9K | $23.79 | $208K |
| Apr 9, 2026 | Boyd Jeffery H | Director | Grant(A) | 4K | $14.54 | $52K |
| Apr 9, 2026 | Gassen William | Director | Grant(A) | 1K | $14.54 | $21K |
| Apr 9, 2026 | Sankaran Sid | Director | Grant(A) | 1K | $14.54 | $17K |
| Apr 9, 2026 | Plouffe David | Director | Grant(A) | 1K | $14.54 | $21K |
| Apr 6, 2026 | Bertolini Mark T | Chief Executive Officer, Director | Tax withholding(F) | 1.0M | $11.92 | $11.9M |
| Apr 6, 2026 | Bertolini Mark T | Chief Executive Officer, Director | Buy(P) | 1.0M | $11.92 | $11.9M |
| Apr 3, 2026 | Bertolini Mark T | Chief Executive Officer, Director | Option exercise(M) | 5.7M | — | — |
| Apr 3, 2026 | Bertolini Mark T | Chief Executive Officer, Director | Option exercise(M) | 5.7M | — | $0 |
| Mar 12, 2026 | Blackley Richard Scott | Chief Financial Officer | Gift(G) | 75K | — | $0 |
| Mar 12, 2026 | Blackley Richard Scott | Chief Financial Officer | Gift(G) | 75K | — | $0 |
| Mar 12, 2026 | Blackley Richard Scott | Chief Financial Officer | Gift(G) | 75K | — | $0 |
| Mar 2, 2026 | Blackley Richard Scott | Chief Financial Officer | Sell(S) | 19K | $13.39 | $257K |
| Mar 2, 2026 | Blackley Richard Scott | Chief Financial Officer | Grant(A) | 135K | — | $0 |
| Mar 2, 2026 | Schlosser Mario | President of Technology & CTO, Director | Grant(A) | 189K | — | $0 |
| Mar 2, 2026 | Schlosser Mario | President of Technology & CTO, Director | Sell(S) | 24K | $13.39 | $326K |
| Mar 2, 2026 | McAnaney Adam | Chief Legal Officer | Sell(S) | 19K | $13.39 | $251K |
| Mar 2, 2026 | McAnaney Adam | Chief Legal Officer | Grant(A) | 67K | — | $0 |
| Mar 2, 2026 | Baltrus Victoria | Chief Accounting Officer | Sell(S) | 5K | $13.39 | $62K |
| Mar 2, 2026 | Baltrus Victoria | Chief Accounting Officer | Grant(A) | 17K | — | $0 |
| Mar 2, 2026 | Bertolini Mark T | Chief Executive Officer, Director | Grant(A) | 1.6M | — | $0 |
| Mar 2, 2026 | Liang Janet | President, Oscar Insurance | Sell(S) | 7K | $13.39 | $100K |
| Mar 2, 2026 | Liang Janet | President, Oscar Insurance | Grant(A) | 106K | — | $0 |
| Jan 8, 2026 | Boyd Jeffery H | Director | Grant(A) | 3K | $16.90 | $52K |
| Jan 8, 2026 | Plouffe David | Director | Grant(A) | 1K | $16.90 | $21K |
| Jan 8, 2026 | Schlosser Mario | President of Technology & CTO, Director | Conversion(C) | 23K | — | — |
| Jan 8, 2026 | Schlosser Mario | President of Technology & CTO, Director | Sell(S) | 23K | $17.65 | $407K |
| Jan 8, 2026 | Schlosser Mario | President of Technology & CTO, Director | Conversion(C) | 23K | — | $0 |
| Jan 8, 2026 | Gassen William | Director | Grant(A) | 1K | $16.90 | $21K |
| Jan 6, 2026 | Schlosser Mario | President of Technology & CTO, Director | Conversion(C) | 77K | — | — |
| Jan 6, 2026 | Schlosser Mario | President of Technology & CTO, Director | Sell(S) | 77K | $17.01 | $1.3M |
| Jan 6, 2026 | Schlosser Mario | President of Technology & CTO, Director | Conversion(C) | 77K | — | $0 |
| Jan 5, 2026 | Schlosser Mario | President of Technology & CTO, Director | Sell(S) | 97K | $15.64 | $1.5M |
| Jan 5, 2026 | Schlosser Mario | President of Technology & CTO, Director | Conversion(C) | 87K | — | — |
| Jan 5, 2026 | Schlosser Mario | President of Technology & CTO, Director | Conversion(C) | 87K | — | $0 |
| Jan 2, 2026 | Schlosser Mario | President of Technology & CTO, Director | Sell(S) | 138K | $15.02 | $2.1M |
| Jan 2, 2026 | Schlosser Mario | President of Technology & CTO, Director | Conversion(C) | 60K | — | — |
| Jan 2, 2026 | Schlosser Mario | President of Technology & CTO, Director | Conversion(C) | 60K | — | $0 |
| Dec 24, 2025 | Schlosser Mario | President of Technology & CTO, Director | Sell(S) | 39K | $15.00 | $583K |
| Dec 2, 2025 | Blackley Richard Scott | Chief Financial Officer | Sell(S) | 25K | $16.59 | $417K |
| Dec 2, 2025 | McAnaney Adam | Chief Legal Officer | Sell(S) | 2K | $16.59 | $31K |
| Dec 2, 2025 | Schlosser Mario | President of Technology & CTO, Director | Sell(S) | 24K | $16.59 | $398K |
| Dec 2, 2025 | Liang Janet | President, Oscar Insurance | Sell(S) | 7K | $16.59 | $122K |
| Dec 2, 2025 | Baltrus Victoria | Chief Accounting Officer | Sell(S) | 4K | $16.59 | $69K |
| Nov 12, 2025 | Schlosser Mario | President of Technology & CTO, Director | Conversion(C) | 105K | — | — |
Insider transactions sourced from SEC EDGAR Form 4 filings, normalized within minutes of acceptance. "Buy"/"Sell" mark open-market transactions (codes P/S), the tradeable signal. Awards, option exercises and tax-withholding are shown with their raw code. All data is public domain.
Coverage: Form 4 filings indexed 2021-01-04 → 2026-07-20. Earlier history is backfilling; this window widens as it deepens.
Programmatic access via the Arkolith API & MCP server (insider.transactions, insider.company).