There have been 50 recent insider transactions recorded for Oscar Health, Inc. (OSCR), including 18 buys and 31 sells. Total insider buying was valued at RSU Award and total insider selling at $33.11M.
Notable insiders with recent activity include Bertolini Mark T, Blackley Richard Scott, Mcananey Adam. Insider transactions can provide insights into how company leadership views the stock's valuation and future prospects.
Insider Transactions — OSCR
| Date |
Name |
Role |
Transaction |
Shares |
Avg. Price |
Value |
Shares Owned |
| 2026-04-06 |
Bertolini Mark T |
Chief Executive Officer |
Tax Withholding of RSU |
1,000,001 |
$11.92 |
$11.92M |
9,196,876 |
| 2026-04-03 |
Bertolini Mark T |
Chief Executive Officer |
Option Exercise (Sell) |
5,733,334 |
- |
- |
- |
| 2026-03-12 |
Blackley Richard Scott |
Chief Financial Officer |
Gift (Received) |
75,000 |
- |
- |
75,000 |
| 2026-03-02 |
Bertolini Mark T |
Chief Executive Officer |
RSU Award |
1,596,877 |
- |
- |
4,463,543 |
| 2026-03-02 |
Blackley Richard Scott |
Chief Financial Officer |
Informative Sell |
19,221 |
$13.39 |
$257.37K |
1,466,660 |
| 2026-03-02 |
Mcananey Adam |
Chief Legal Officer |
Informative Sell |
18,710 |
$13.39 |
$250.53K |
227,955 |
| 2026-03-02 |
Schlosser Mario |
President of Technology & CTO |
Informative Sell |
24,335 |
$13.39 |
$325.85K |
514,986 |
| 2026-03-02 |
Liang Janet |
President, Oscar Insurance |
Informative Sell |
7,453 |
$13.39 |
$99.8K |
271,532 |
| 2026-03-02 |
Baltrus Victoria |
Chief Accounting Officer |
Informative Sell |
4,638 |
$13.39 |
$62.1K |
216,112 |
| 2026-01-08 |
Boyd Jeffery H |
Director |
RSU Award |
3,106 |
- |
- |
66,248 |
| 2026-01-08 |
Plouffe David |
Director |
RSU Award |
1,257 |
- |
- |
5,393 |
| 2026-01-08 |
Schlosser Mario |
President of Technology & CTO |
Informative Sell |
23,038 |
$17.65 |
$406.62K |
350,180 |
| 2026-01-08 |
Gassen William |
Director |
RSU Award |
1,220 |
- |
- |
4,969 |
| 2026-01-06 |
Schlosser Mario |
President of Technology & CTO |
Informative Sell |
76,962 |
$17.01 |
$1.31M |
350,180 |
| 2026-01-05 |
Schlosser Mario |
President of Technology & CTO |
Informative Sell |
96,928 |
$15.64 |
$1.52M |
350,180 |
| 2026-01-02 |
Schlosser Mario |
President of Technology & CTO |
Informative Sell |
137,933 |
$15.02 |
$2.07M |
360,215 |
| 2025-12-24 |
Schlosser Mario |
President of Technology & CTO |
Informative Sell |
38,835 |
$15.00 |
$582.53K |
438,348 |
| 2025-12-02 |
Blackley Richard Scott |
Chief Financial Officer |
Informative Sell |
25,135 |
$16.59 |
$416.99K |
1,351,034 |
| 2025-12-02 |
Mcananey Adam |
Chief Legal Officer |
Informative Sell |
1,852 |
$16.59 |
$30.72K |
179,241 |
| 2025-12-02 |
Schlosser Mario |
President of Technology & CTO |
Informative Sell |
23,965 |
$16.59 |
$397.58K |
477,183 |
| 2025-12-02 |
Liang Janet |
President, Oscar Insurance |
Informative Sell |
7,338 |
$16.59 |
$121.74K |
172,527 |
| 2025-12-02 |
Baltrus Victoria |
Chief Accounting Officer |
Informative Sell |
4,149 |
$16.59 |
$68.83K |
203,450 |
| 2025-11-12 |
Schlosser Mario |
President of Technology & CTO |
Option Exercise (Sell) |
141,330 |
$6.36 |
$898.86K |
- |
| 2025-11-11 |
Schlosser Mario |
President of Technology & CTO |
Option Exercise (Sell) |
413,835 |
$6.36 |
$2.63M |
141,330 |
| 2025-10-09 |
Boyd Jeffery H |
Director |
RSU Award |
2,555 |
- |
- |
63,142 |
| 2025-10-09 |
Plouffe David |
Director |
RSU Award |
1,034 |
- |
- |
4,136 |
| 2025-10-09 |
Gassen William |
Director |
RSU Award |
1,004 |
- |
- |
3,749 |
| 2025-09-22 |
Schlosser Mario |
President of Technology & CTO |
Informative Sell |
395,000 |
$18.43 |
$7.28M |
501,148 |
| 2025-09-02 |
Blackley Richard Scott |
Chief Financial Officer |
Tax Withholding of RSU |
28,166 |
$16.66 |
$469.25K |
1,376,169 |
| 2025-09-02 |
Mcananey Adam |
Chief Legal Officer |
Tax Withholding of RSU |
1,845 |
$16.66 |
$30.74K |
181,093 |
| 2025-09-02 |
Schlosser Mario |
President of Technology & CTO |
Tax Withholding of RSU |
23,879 |
$16.66 |
$397.82K |
501,148 |
| 2025-09-02 |
Liang Janet |
President, Oscar Insurance |
Tax Withholding of RSU |
7,303 |
$16.66 |
$121.67K |
179,865 |
| 2025-09-02 |
Baltrus Victoria |
Chief Accounting Officer |
Tax Withholding of RSU |
6,266 |
$16.66 |
$104.39K |
207,599 |
| 2025-07-10 |
Boyd Jeffery H |
Director |
RSU Award |
3,380 |
- |
- |
60,587 |
| 2025-07-10 |
Plouffe David |
Director |
RSU Award |
1,368 |
- |
- |
3,102 |
| 2025-07-10 |
Gassen William |
Director |
RSU Award |
1,215 |
- |
- |
2,745 |
| 2025-06-04 |
Boyd Jeffery H |
Director |
RSU Award |
14,134 |
- |
- |
705,673 |
| 2025-06-04 |
Wittman Vanessa Ames |
Director |
RSU Award |
14,134 |
- |
- |
128,646 |
| 2025-06-04 |
Lang Laura W |
Director |
RSU Award |
14,134 |
- |
- |
74,365 |
| 2025-06-04 |
Sankaran Sid |
Director |
RSU Award |
14,134 |
- |
- |
14,134 |
| 2025-06-04 |
Plouffe David |
Director |
RSU Award |
14,134 |
- |
- |
128,646 |
| 2025-06-04 |
Gassen William |
Director |
RSU Award |
14,134 |
- |
- |
74,365 |
| 2025-06-02 |
Blackley Richard Scott |
Chief Financial Officer |
Tax Withholding of RSU |
28,185 |
$13.80 |
$388.95K |
1,404,335 |
| 2025-06-02 |
Mcananey Adam |
Chief Legal Officer |
Tax Withholding of RSU |
1,847 |
$13.80 |
$25.49K |
182,938 |
| 2025-06-02 |
Schlosser Mario |
President of Technology & CTO |
Tax Withholding of RSU |
23,879 |
$13.80 |
$329.53K |
525,027 |
| 2025-06-02 |
Liang Janet |
President, Oscar Insurance |
Tax Withholding of RSU |
7,196 |
$13.80 |
$99.3K |
187,168 |
| 2025-06-02 |
Baltrus Victoria |
Chief Accounting Officer |
Tax Withholding of RSU |
6,265 |
$13.80 |
$86.46K |
213,865 |
| 2025-05-12 |
Robinson Elbert O. Jr. |
Director |
Informative Sell |
25,000 |
$16.43 |
$410.75K |
64,512 |
| 2025-04-10 |
Boyd Jeffery H |
Director |
RSU Award |
4,285 |
- |
- |
57,207 |
| 2025-04-10 |
Plouffe David |
Director |
RSU Award |
1,734 |
- |
- |
1,734 |
■ Informative Buy/Sell — open market transaction (most significant)
■ Uninformative Buy — award, option exercise, conversion
■ Uninformative Sell — tax withholding, award vest sale
■ Neutral — gift, trust, expiry
