As of September 09, 2026, Oscar Health's top three insider holders are Mark T Bertolini (Chief Executive Officer, 7.75Mn shares), Partners Vii Growth Gp, Llc Thrive (Director, 6.34Mn shares), Partners Vii Growth Gp, Llc Thrive (Director, 6.34Mn shares).
| # | Insider | Position | Direct | Indirect | Total | Share of Insiders | Last Filed |
|---|---|---|---|---|---|---|---|
| 1 | Mark T Bertolini | Chief Executive Officer | 7,751,570 | 0 | 7,751,570 | 31.3% | 01 Jul, 2026 |
| 2 | Partners Vii Growth Gp, Llc Thrive | Director, TenPercentOwner | 0 | 6,343,617 | 6,343,617 | 25.6% | 22 Nov, 2024 |
| 3 | Joshua Kushner | Co Founder And Vice Chairman | 0 | 6,343,617 | 6,343,617 | 25.6% | 22 Nov, 2024 |
| 4 | Richard Scott Blackley | Chief Financial Officer | 1,046,108 | 0 | 1,046,108 | 4.2% | 08 Sep, 2026 |
| 5 | Jeffery H Boyd | Director | 705,673 | 0 | 705,673 | 2.8% | 06 Jun, 2025 |
| 6 | Mario Schlosser | President Of Technology Cto | 449,444 | 0 | 449,444 | 1.8% | 08 Sep, 2026 |
| 7 | Alessandrea C. Quane | Evp, Chief Insurance Officer | 430,216 | 0 | 430,216 | 1.7% | 09 Dec, 2024 |
| 8 | Janet Liang | President, Oscar Insurance | 248,697 | 0 | 248,697 | 1.0% | 08 Sep, 2026 |
| 9 | Ranmali Bopitiya | Evp Chief Legal Officer | 241,488 | 0 | 241,488 | 1.0% | 03 Dec, 2024 |
| 10 | Victoria Baltrus | Chief Accounting Officer | 213,631 | 0 | 213,631 | 0.9% | 08 Sep, 2026 |
| 11 | Adam Mcananey | Chief Legal Officer | 209,004 | 0 | 209,004 | 0.8% | 08 Sep, 2026 |
| 12 | Vanessa Ames Wittman | Director | 137,121 | 0 | 137,121 | 0.6% | 08 Jun, 2026 |
| 13 | David Plouffe | Director | 137,121 | 0 | 137,121 | 0.6% | 08 Jun, 2026 |
| 14 | Steven Wolin | Chief Operating Officer | 102,598 | 0 | 102,598 | 0.4% | 03 Dec, 2024 |
| 15 | Jr Charles E Phillips | Director | 85,787 | 0 | 85,787 | 0.3% | 13 Jun, 2022 |
| 16 | Laura W Lang | Director | 82,840 | 0 | 82,840 | 0.3% | 08 Jun, 2026 |
| 17 | William Gassen | Director | 82,840 | 0 | 82,840 | 0.3% | 08 Jun, 2026 |
| 18 | Elbert O. Jr. Robinson | Director | 64,512 | 0 | 64,512 | 0.3% | 14 May, 2025 |
| 19 | Meghan V. Joyce | Chief Operating Officer | 43,070 | 0 | 43,070 | 0.2% | 03 Mar, 2022 |
| 20 | Dennis Weaver | Chief Clinical Officer | 27,110 | 0 | 27,110 | 0.1% | 05 Dec, 2022 |
| 21 | Sid Sankaran | Interim Cfo | 22,609 | 0 | 22,609 | 0.1% | 08 Jun, 2026 |
Each row is that insider’s most recently reported position, from Form 4 filings over the last 60 months — which is why this total does not tie to the quarterly series above, where a quarter counts only the insiders who filed in it. Shares held through a fund or institutional portfolio are counted on the institutional ownership page instead.
| Date | Insider | Position | Transaction | Shares | Price | Value | Shares Held After | Ownership |
|---|---|---|---|---|---|---|---|---|
| 03 Sep, 2026 | Mario Schlosser | Director | Disposed S | 31,422 | $31.45 | $988.22K | 449,444 | Direct |
| 03 Sep, 2026 | Victoria Baltrus | Chief Accounting Officer | Disposed S | 958 | $31.45 | $30.13K | 213,631 | Direct |
| 03 Sep, 2026 | Richard Scott Blackley | Chief Financial Officer | Disposed S | 28,869 | $31.45 | $907.93K | 1,046,108 | Direct |
| 03 Sep, 2026 | Janet Liang | President, Oscar Insurance | Disposed S | 10,360 | $31.45 | $325.82K | 248,697 | Direct |
| 03 Sep, 2026 | Adam Mcananey | Chief Legal Officer | Disposed S | 9,092 | $31.45 | $285.94K | 209,004 | Direct |
| 27 Aug, 2026 | Mario Schlosser | Director | Acquired C | 600,000 | — | — | 1,080,866 | Direct |
| 27 Aug, 2026 | Mario Schlosser | Director | Disposed S | 600,000 | $30.34 | $18.20Mn | 480,866 | Direct |
| 28 Aug, 2026 | Mario Schlosser | Director | Acquired C | 150,000 | — | — | 630,866 | Direct |
| 28 Aug, 2026 | Mario Schlosser | Director | Disposed S | 150,000 | $30.79 | $4.62Mn | 480,866 | Direct |
| 27 Aug, 2026 | Mario Schlosser | Director | Disposed M | 600,000 | $0.00 | $0 | 3,140,000 | Direct |
| 27 Aug, 2026 | Mario Schlosser | Director | Acquired M | 600,000 | $9.75 | $5.85Mn | 1,812,293 | Direct |
| 27 Aug, 2026 | Mario Schlosser | Director | Disposed C | 600,000 | $0.00 | $0 | 1,212,293 | Direct |
| 28 Aug, 2026 | Mario Schlosser | Director | Disposed M | 150,000 | $0.00 | $0 | 2,990,000 | Direct |
| 28 Aug, 2026 | Mario Schlosser | Director | Acquired M | 150,000 | $9.75 | $1.46Mn | 1,362,293 | Direct |
| 28 Aug, 2026 | Mario Schlosser | Director | Disposed C | 150,000 | $0.00 | $0 | 1,212,293 | Direct |
| 18 Aug, 2026 | Richard Scott Blackley | Chief Financial Officer | Disposed S | 18,750 | $31.74 | $595.13K | 56,250 | Indirect |
| 09 Jul, 2026 | Sid Sankaran | Director | Acquired A | 858 | $31.20 | $26.77K | 2,061 | Direct |
| 09 Jul, 2026 | David Plouffe | Director | Acquired A | 681 | $31.20 | $21.25K | 7,535 | Direct |
| 09 Jul, 2026 | William Gassen | Director | Acquired A | 684 | $31.20 | $21.34K | 7,071 | Direct |
| 01 Jul, 2026 | Mario Schlosser | Director | Acquired C | 47,500 | — | — | 47,500 | Indirect |