OSCR · Insider Trading
Oscar Health, Inc.
Every open-market purchase and sale reported by OSCR officers, directors and 10%+ beneficial owners on SEC Form 4, which must be filed within two business days of the transaction. Sales often reflect scheduled 10b5-1 plans or tax withholding rather than a directional view, so read counts alongside the size and the filer.
| Filed | Insider | Role | Type | Shares | Value |
|---|---|---|---|---|---|
| 2026-10-13 | David Plouffe | Director | A | +641 deriv. | — |
| 2026-10-13 | Sid Sankaran | Director | A | +1,472 deriv. | — |
| 2026-10-13 | William Gassen | Director | A | +698 deriv. | — |
| 2026-09-22 | Vanessa Ames Wittman | Director | Sell | −25,000 | −$806.00K |
| 2026-09-18 | Joshua Kushner | Co-Founder and Vice Chairman | J | −6,343,617 | — |
| 2026-09-18 | Thrive Partners II GP, LLC | Director | J | −57,092,553 | — |
| 2026-09-08 | Victoria Baltrus | Chief Accounting Officer | Sell | −958 | −$30.13K |
| 2026-09-08 | Richard Scott Blackley | Chief Financial Officer | Sell | −28,869 | −$907.93K |
| 2026-09-08 | Mario Schlosser | Director | Sell | −31,422 | −$988.22K |
| 2026-09-08 | Janet Liang | President, Oscar Insurance | Sell | −10,360 | −$325.82K |
| 2026-09-08 | Adam McAnaney | Chief Legal Officer | Sell | −9,092 | −$285.94K |
| 2026-08-31 | Mario Schlosser | Director | MIXED | — | −$22.82M |
| 2026-08-20 | Richard Scott Blackley | Chief Financial Officer | Sell | −18,750 | −$595.12K |
| 2026-07-13 | Sid Sankaran | Director | A | +858 deriv. | — |
| 2026-07-13 | David Plouffe | Director | A | +681 deriv. | — |
| 2026-07-13 | William Gassen | Director | A | +684 deriv. | — |
| 2026-07-06 | Mario Schlosser | Director | MIXED | — | −$1.48M |
| 2026-07-01 | Mark T Bertolini | Chief Executive Officer | Sell | −1,238,996 | −$35.77M |
| 2026-06-29 | Mark T Bertolini | Chief Executive Officer | Sell | −1,206,310 | −$34.91M |
| 2026-06-25 | Mario Schlosser | Director | MIXED | — | −$30.18M |
| 2026-06-08 | William Gassen | Director | A | +8,475 | — |
| 2026-06-08 | Sid Sankaran | Director | A | +8,475 | — |
| 2026-06-08 | David Plouffe | Director | A | +8,475 | — |
| 2026-06-08 | Laura W Lang | Director | A | +8,475 | — |
| 2026-06-08 | Vanessa Ames Wittman | Director | A | +8,475 | — |
| 2026-06-04 | Richard Scott Blackley | Chief Financial Officer | Sell | −31,683 | −$695.16K |
| 2026-06-04 | Victoria Baltrus | Chief Accounting Officer | Sell | −1,523 | −$33.42K |
| 2026-06-04 | Adam McAnaney | Chief Legal Officer | Sell | −9,859 | −$216.32K |
| 2026-06-04 | Janet Liang | President, Oscar Insurance | Sell | −12,475 | −$273.72K |
| 2026-06-04 | Mario Schlosser | Director | Sell | −34,120 | −$748.63K |
| 2026-05-20 | Richard Scott Blackley | Chief Financial Officer | Sell | −110,000 | −$2.75M |
| 2026-05-18 | Richard Scott Blackley | Chief Financial Officer | Sell | −100,000 | −$2.32M |
| 2026-04-13 | Sid Sankaran | Director | A | +1,203 deriv. | — |
| 2026-04-13 | Jeffery H Boyd | Director | A | +3,610 deriv. | — |
| 2026-04-13 | David Plouffe | Director | A | +1,461 deriv. | — |
| 2026-04-13 | William Gassen | Director | A | +1,418 deriv. | — |
| 2026-04-07 | Mark T Bertolini | Chief Executive Officer | MIXED | +5,733,333 | −$12 |
| 2026-03-16 | Richard Scott Blackley | Chief Financial Officer | G | −75,000 | — |
| 2026-03-04 | Mark T Bertolini | Chief Executive Officer | A | +1,596,877 | — |
| 2026-03-04 | Mario Schlosser | President of Technology & CTO | MIXED | +164,806 | −$325.85K |
| 2026-03-04 | Adam McAnaney | Chief Legal Officer | MIXED | +48,714 | −$250.53K |
| 2026-03-04 | Richard Scott Blackley | Chief Financial Officer | MIXED | +115,626 | −$257.37K |
| 2026-03-04 | Victoria Baltrus | Chief Accounting Officer | MIXED | +12,662 | −$62.10K |
| 2026-03-04 | Janet Liang | President, Oscar Insurance | MIXED | +99,005 | −$99.80K |
| 2026-01-12 | William Gassen | Director | A | +1,220 deriv. | — |
| 2026-01-12 | Mario Schlosser | President of Technology & CTO | MIXED | — | −$406.62K |
| 2026-01-12 | David Plouffe | Director | A | +1,257 deriv. | — |
| 2026-01-12 | Jeffery H Boyd | Director | A | +3,106 deriv. | — |
| 2026-01-08 | Mario Schlosser | President of Technology & CTO | MIXED | — | −$1.31M |
| 2026-01-06 | Mario Schlosser | President of Technology & CTO | MIXED | −88,168 | −$3.59M |
| Insider | Role | Shares Held | Value |
|---|---|---|---|
| Mark T Bertolini | Chief Executive Officer | 8,434,740 | $274.47M |
| Claremount VII Associates, L.P. | Director | 6,343,617 | $206.42M |
| Thrive Capital Partners VII Growth, L.P. | Director | 6,155,222 | $200.29M |
| Thrive Partners VII GP, LLC | Director | 5,810,700 | $189.08M |
| Richard Scott Blackley | Chief Financial Officer | 1,102,358 | $35.87M |
| Sid Sankaran | Director | 818,295 | $26.63M |
| Jeffery H Boyd | Director | 705,673 | $22.96M |
| Alessandrea C. Quane | EVP, Chief Insurance Officer | 523,866 | $17.05M |
| Mario Schlosser | Director | 449,444 | $14.62M |
| Ranmali Bopitiya | EVP & Chief Legal Officer | 255,778 | $8.32M |
| Janet Liang | President, Oscar Insurance | 248,697 | $8.09M |
| Victoria Baltrus | Chief Accounting Officer | 213,631 | $6.95M |
| Adam McAnaney | Chief Legal Officer | 209,004 | $6.80M |
| David Plouffe | Director | 137,121 | $4.46M |
| Vanessa Ames Wittman | Director | 112,121 | $3.65M |
| Steven Wolin | Chief Operating Officer | 102,951 | $3.35M |
| Laura W Lang | Director | 82,840 | $2.70M |
| William Gassen | Director | 82,840 | $2.70M |
| Elbert O. Robinson Jr. | Director | 64,512 | $2.10M |
Form 4 reports a change in beneficial ownership by an officer, director or 10%+ holder, and must be filed within two business days of the transaction — so this is close to real time, unlike the 45-day-lagged 13F institutional data.
Transaction codes matter more than the raw buy/sell count. Code P is an open-market purchase — an insider choosing to buy with their own money, which is the signal most research treats as informative. Code S is a sale, but sales are frequently pre-scheduled under a 10b5-1 plan or cover tax withholding on vesting equity, so a run of sales often says nothing directional. Codes A and M are grants and option exercises rather than open-market decisions.
Full filing history and per-insider positions are on the OSCR quote page; the site-wide leaderboard is on the insider transactions hub.
Market data may be delayed, incomplete, or inaccurate. Not a recommendation to buy, sell, or hold any security. Verify quotes with your broker before trading. See Terms §17.