OSCROscar Health, Inc. · Insider ownership research

Oscar Health, Inc. insiders sold $150M in the past 12 months. How much of their stake is that?

Insiders sold $150M in the past 12 months.80% was sold under disclosed trading plans, 4% to cover taxes, 16% with no plan disclosed. The largest seller, Mark Bertolini (Chief Executive Officer, Director), sold $70.7M. 32% of these sales were shares from exercising options.Share-of-stake figures for this company are being verified and will be added when that check is finished. Why

Updated Oct 13, 2026 from SEC filings · covers Oct 14, 2025 to Oct 13, 2026

$23.4M

sold with no plan disclosed, past 12 months

80%

of sales were under disclosed trading plans, past 12 months

7 of 14

officers and directors sold shares, past 12 months

Is this normal? More than usual: about 7x the 4-year average. 7 insiders sold; the average is 6 a year. Year by year

Latest filing: Filed Sep 22 for a sale on Sep 18. Vanessa Wittman sold 25K shares ($806K) under a disclosed plan. Filing

SEC ownership filings: 57 filed in the 12 months to Oct 13, 2026; 313 on record since Mar 3, 2021 · See the evidence

What stands out

Mario Schlosser sold $22.8M of stock with no disclosed trading plan. The filings don't state a reason.Largest such sale, Aug 27, 2026

A share of stake is shown for 0 of the 7 officers and directors who sold. 14 are left out

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Left out: Joshua Kushner, Mario Schlosser, Mark Bertolini, Richard Blackley, Sid Sankaran, Jeffery Boyd, Victoria Baltrus, Adam McAnaney, Janet Liang, Vanessa Wittman, David Plouffe, Laura Lang, William Gassen and Elbert Robinson Jr. (share of stake is being verified).

Disclosed company stock is not an insider's whole wealth.

Who sold, and how much of their stake

Officers and directors, past 12 months. Their share of stake is being verified and is not shown yet; amounts and trading plans are below.

Mark Bertolini

Chief Executive Officer, Director

Not confirmed

Share of stake not shown: share of stake is being verified. Why

$70.7MDisclosed plan

Mario Schlosser

Director

Not confirmed

Share of stake not shown: share of stake is being verified. Why

$68.8M58% planned, 9% to cover taxes 33% no plan disclosed

Richard Blackley

Chief Financial Officer

Not confirmed

Share of stake not shown: share of stake is being verified. Why

$7.9M93% planned 7% no plan disclosed

Janet Liang

President, Oscar Insurance

Not confirmed

Share of stake not shown: share of stake is being verified. Why

$821KDisclosed plan

Vanessa Wittman

Director

Not confirmed

Share of stake not shown: share of stake is being verified. Why

$806KDisclosed plan

Selling by month

Officers and directors, Oct 2025 to Oct 2026. Each sale is counted once: under a disclosed plan, else to cover taxes, else no plan disclosed.

Disclosed planTo cover taxesNo plan disclosedOne dollar scale for every month; the tallest bar is labeled

Recent activity

Past 30 days, Sep 14, 2026 to Oct 13, 2026

Sep 18, 2026Vanessa Wittman sold 25K shares ($806K) under a disclosed trading plan.

Who	Shares	Price	% of total stake	Total stake after	Trade date	Filed
Vanessa Wittman Director	25,000	$32.24	n/a	n/a	Sep 18, 2026	Sep 22, 2026

"% of total stake" is the shares in an event against all the vested shares the person held that day, across every share class and holding entity, after that day's vesting. "n/a" means the person's holdings are not confirmed, or the row is a purchase. "Holdings record incomplete" means more shares were sold than the filings show the person held that day, so a percentage would be wrong.

Outside holders, reported separately

Thrive Partners VII Growth GP, LLC reported no open-market sales in the past 12 months. Large shareholders and the funds or companies that board members represent are not part of management, so they are left out of the figures above.

Common questions

Is the Oscar Health, Inc. CEO selling stock?

Yes. Mark Bertolini sold 2.45M shares ($70.7M) in the past 12 months, all of it under a trading plan disclosed in the filings.

Why are Oscar Health, Inc. insiders selling?

Filings rarely give a reason, and we don't guess at one. What they show is how the sales were made: 80% of sales by value ran under 10b5-1 trading plans disclosed in the filings, 4% were to cover taxes and 16% had no disclosed plan. A trading plan schedules sales in advance.

Are any Oscar Health, Inc. insiders buying?

No. Officers and directors reported no purchases in the past 12 months.

The evidence

Who sold7 officers and directors: amount, % of holdings, trading plan

Who sold	Amount	% of holdings	Trading plan
Mark Bertolini Chief Executive Officer, Director	$70.7M 2.45M shares	Not confirmed share of stake is being verified. Why	Disclosed plan
Mario Schlosser Director	$68.8M 2.70M shares	Not confirmed share of stake is being verified. Why	58% under a disclosed plan, 9% to cover taxes 33% no plan disclosed
Richard Blackley Chief Financial Officer	$7.9M 334K shares	Not confirmed share of stake is being verified. Why	93% under a disclosed plan 7% no plan disclosed
Janet Liang President, Oscar Insurance	$821K 38K shares	Not confirmed share of stake is being verified. Why	Disclosed plan
Vanessa Wittman Director	$806K 25K shares	Not confirmed share of stake is being verified. Why	Disclosed plan
Adam McAnaney Chief Legal Officer	$784K 40K shares	Not confirmed share of stake is being verified. Why	Disclosed plan
Victoria Baltrus Chief Accounting Officer	$194K 11K shares	Not confirmed share of stake is being verified. Why	Disclosed plan

Outside holder, reported separately: Thrive Partners VII Growth GP, LLC (a 10% owner, not part of management). No open-market sales reported in the period. Latest filing

The full ownership picture0 of 14 officers and directors confirmed

Vested shares across all share classes, held directly and through trusts, LLCs and family members, as reported on SEC Forms 3, 4 and 5. Unvested awards and options are never counted as owned shares.

Insider

Held Oct 13, 2025

Sold

Held Oct 13, 2026

Still held

Joshua Kushner

!

Holdings and share of stake are being verified. Share-of-stake figures and holdings for this company are held back while they are verified. Sales and other transactions for Joshua Kushner are complete.

Co-Founder and Vice Chairman, Director

n/a

0

n/a

n/a

Vesting, gifts, unvested awards and holding lines for Joshua Kushner

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for Joshua Kushner are complete; balances and unit counts will be added when the check is finished.

0gifted (net of own trusts)

Mario Schlosser

!

Holdings and share of stake are being verified. Share-of-stake figures and holdings for this company are held back while they are verified. Sales and other transactions for Mario Schlosser are complete.

Director

n/a

−2.70M

n/a

n/a

Vesting, gifts, unvested awards and holding lines for Mario Schlosser

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for Mario Schlosser are complete; balances and unit counts will be added when the check is finished.

0gifted (net of own trusts)

Stock options (not counted as shares):

Options held	Strike price	Expires	Intrinsic value (estimate)
2,990,000	$9.75	Dec 16, 2029	$67.2M

Estimate: options held × ($32.24 − strike price), using the most recent insider trade price on Form 4 (Sep 18, 2026), not a market close.

Mark Bertolini

!

Holdings and share of stake are being verified. Share-of-stake figures and holdings for this company are held back while they are verified. Sales and other transactions for Mark Bertolini are complete.

Chief Executive Officer, Director

n/a

−2.45M

n/a

n/a

Vesting, gifts, unvested awards and holding lines for Mark Bertolini

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for Mark Bertolini are complete; balances and unit counts will be added when the check is finished.

0gifted (net of own trusts)

−1.00Mwithheld by the company for taxes

Richard Blackley

!

Holdings and share of stake are being verified. Share-of-stake figures and holdings for this company are held back while they are verified. Sales and other transactions for Richard Blackley are complete.

Chief Financial Officer

n/a

−334K

n/a

n/a

Vesting, gifts, unvested awards and holding lines for Richard Blackley

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for Richard Blackley are complete; balances and unit counts will be added when the check is finished.

−75Kgifted (net of own trusts)

Sid Sankaran

!

Holdings and share of stake are being verified. Share-of-stake figures and holdings for this company are held back while they are verified. Sales and other transactions for Sid Sankaran are complete.

Director

n/a

0

n/a

n/a

Vesting, gifts, unvested awards and holding lines for Sid Sankaran

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for Sid Sankaran are complete; balances and unit counts will be added when the check is finished.

0gifted (net of own trusts)

Jeffery Boyd

!

Holdings and share of stake are being verified. Share-of-stake figures and holdings for this company are held back while they are verified. Sales and other transactions for Jeffery Boyd are complete.

Director

n/a

0

n/a

n/a

Vesting, gifts, unvested awards and holding lines for Jeffery Boyd

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for Jeffery Boyd are complete; balances and unit counts will be added when the check is finished.

0gifted (net of own trusts)

Victoria Baltrus

!

Holdings and share of stake are being verified. Share-of-stake figures and holdings for this company are held back while they are verified. Sales and other transactions for Victoria Baltrus are complete.

Chief Accounting Officer

n/a

−11K

n/a

n/a

Vesting, gifts, unvested awards and holding lines for Victoria Baltrus

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for Victoria Baltrus are complete; balances and unit counts will be added when the check is finished.

0gifted (net of own trusts)

Adam McAnaney

!

Holdings and share of stake are being verified. Share-of-stake figures and holdings for this company are held back while they are verified. Sales and other transactions for Adam McAnaney are complete.

Chief Legal Officer

n/a

−40K

n/a

n/a

Vesting, gifts, unvested awards and holding lines for Adam McAnaney

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for Adam McAnaney are complete; balances and unit counts will be added when the check is finished.

0gifted (net of own trusts)

Stock options (not counted as shares):

Options held	Strike price	Expires	Intrinsic value (estimate)
185,004	$15.27	Feb 24, 2035	$3.1M

Estimate: options held × ($32.24 − strike price), using the most recent insider trade price on Form 4 (Sep 18, 2026), not a market close.

Janet Liang

!

Holdings and share of stake are being verified. Share-of-stake figures and holdings for this company are held back while they are verified. Sales and other transactions for Janet Liang are complete.

President, Oscar Insurance

n/a

−38K

n/a

n/a

Vesting, gifts, unvested awards and holding lines for Janet Liang

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for Janet Liang are complete; balances and unit counts will be added when the check is finished.

0gifted (net of own trusts)

Stock options (not counted as shares):

Options held	Strike price	Expires	Intrinsic value (estimate)
147,637	$15.27	Feb 24, 2035	$2.5M

Estimate: options held × ($32.24 − strike price), using the most recent insider trade price on Form 4 (Sep 18, 2026), not a market close.

Vanessa Wittman

!

Holdings and share of stake are being verified. Share-of-stake figures and holdings for this company are held back while they are verified. Sales and other transactions for Vanessa Wittman are complete.

Director

n/a

−25K

n/a

n/a

Vesting, gifts, unvested awards and holding lines for Vanessa Wittman

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for Vanessa Wittman are complete; balances and unit counts will be added when the check is finished.

0gifted (net of own trusts)

David Plouffe

!

Holdings and share of stake are being verified. Share-of-stake figures and holdings for this company are held back while they are verified. Sales and other transactions for David Plouffe are complete.

Director

n/a

0

n/a

n/a

Vesting, gifts, unvested awards and holding lines for David Plouffe

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for David Plouffe are complete; balances and unit counts will be added when the check is finished.

0gifted (net of own trusts)

Laura Lang

!

Holdings and share of stake are being verified. Share-of-stake figures and holdings for this company are held back while they are verified. Sales and other transactions for Laura Lang are complete.

Director

n/a

0

n/a

n/a

Vesting, gifts, unvested awards and holding lines for Laura Lang

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for Laura Lang are complete; balances and unit counts will be added when the check is finished.

0gifted (net of own trusts)

William Gassen

!

Holdings and share of stake are being verified. Share-of-stake figures and holdings for this company are held back while they are verified. Sales and other transactions for William Gassen are complete.

Director

n/a

0

n/a

n/a

Vesting, gifts, unvested awards and holding lines for William Gassen

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for William Gassen are complete; balances and unit counts will be added when the check is finished.

0gifted (net of own trusts)

Elbert Robinson Jr.

!

Holdings and share of stake are being verified. Share-of-stake figures and holdings for this company are held back while they are verified. Sales and other transactions for Elbert Robinson Jr. are complete.

Director

n/a

0

n/a

n/a

Vesting, gifts, unvested awards and holding lines for Elbert Robinson Jr.

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for Elbert Robinson Jr. are complete; balances and unit counts will be added when the check is finished.

0gifted (net of own trusts)

Holdings and share of stake for Oscar Health, Inc. are being verified, so no balances, unit counts or percentages are shown. Sales, proceeds, plan and tax status, titles and dates come straight from individual filings.

What explains the selling$150M of sales by plan status, purpose, seller and month

Officer and director open-market sales: $150M across 5,596,391 shares. Plan status and stated purpose are separate questions, and a sale can have both.

By plan status

Disclosed plan · $121M · 80%

20%

The lighter segment is sales with no plan disclosed in the filing ($29.4M), including tax-related sales outside a plan.

No plan disclosed · $23.4M

Sales with no 10b5-1 plan and no tax reference in the filing. $22.8M of it is Mario Schlosser. No plan disclosed is a statement about the filing, not about why the sale happened. Largest such sale: Mario Schlosser, Aug 27, 2026

Taxes

$83.2M of sales (55.4%) cite tax obligations in their footnotes, $77.2M of them also under a plan. Separately, 1,000,001 shares ($11.9M) were withheld by the company for taxes, which isn't a market sale. Example: Janet Liang, Sep 3, 2026

Seller	Shares sold	Proceeds	Under a disclosed plan	Share of total	Sales dates
Mark Bertolini Chief Executive Officer, Director	2.45M	$70.7M	100%	47%	Jun 25, 2026 to Jun 30, 2026
Mario Schlosser Director	2.70M	$68.8M	58%	46%	Nov 11, 2025 to Sep 3, 2026
Richard Blackley Chief Financial Officer	334K	$7.9M	93%	5%	Dec 2, 2025 to Sep 3, 2026
Janet Liang President, Oscar Insurance	38K	$821K	100%	0.5%	Dec 2, 2025 to Sep 3, 2026
Vanessa Wittman Director	25K	$806K	100%	0.5%	Sep 18, 2026 to Sep 18, 2026
Adam McAnaney Chief Legal Officer	40K	$784K	100%	0.5%	Dec 2, 2025 to Sep 3, 2026
Victoria Baltrus Chief Accounting Officer	11K	$194K	100%	0.1%	Dec 2, 2025 to Sep 3, 2026

Sales by month

Month	Sale proceeds	Disclosed plan	To cover taxes	No plan disclosed
Oct 2025	$0	$0	$0	$0
Nov 2025	$6.0M	$0	$6.0M	$0
Dec 2025	$1.6M	$1.6M	$0	$0
Jan 2026	$5.3M	$5.3M	$0	$0
Feb 2026	$0	$0	$0	$0
Mar 2026	$996K	$996K	$0	$0
Apr 2026	$0	$0	$0	$0
May 2026	$5.1M	$5.1M	$0	$0
Jun 2026	$103M	$103M	$0	$0
Jul 2026	$1.5M	$1.5M	$0	$0
Aug 2026	$23.4M	$0	$0	$23.4M
Sep 2026	$3.3M	$3.3M	$0	$0
Oct 2026	$0	$0	$0	$0

Is this normal? Selling year by year4 earlier years to compare with

More than usual: about 7x the 4-year average. 7 insiders sold; the average is 6 a year.

12 months ending	Shares sold	Insiders who sold	Proceeds
Oct 13, 2026 Latest 12 months	5.60M	7	$150M
Oct 13, 2025 1 year earlier	597K	7	$10.8M
Oct 13, 2024 2 years earlier	1.29M	6	$17.7M
Oct 14, 2023 3 years earlier	942K	7	$5.8M
Oct 14, 2022 4 years earlier	302K	6	$1.3M
Oct 14, 2021 5 years earlier · filings don't cover the whole year	676K	6	$25.8M

Open-market sales (Form 4 code S) by people who were officers or directors, in split-adjusted shares. Earlier years include people who have since left. A sale that an outside holder also reports (a family trust, a fund) is counted with outside holders in every year. Shares, not dollars, are compared, so a change in the stock price doesn't look like a change in selling. Years the filings don't fully cover are shown but left out of the average.

Known gaps and uncertainty14 officers and directors not confirmed

Holdings and share of stake are being verified. Balances, unit counts and every share-of-stake figure for Oscar Health, Inc. are held back until that check is finished. Sales, proceeds, plan and tax status, titles and dates come straight from individual filings and are complete.

External context: we only cite outside events when a documented connection exists. None is shown for this period.

Sources and methodology313 filings on record, 57 filed in the 12-month period, and how we read them

All 313 Forms 3, 4 and 5 on record for Oscar Health, Inc. (SEC CIK 1568651), filed from Mar 3, 2021 to Sep 22, 2026; 57 of them were filed in the 12 months this page covers, retrieved from SEC EDGAR on Oct 13, 2026. Prices are the ones reported in each filing, often weighted averages.

Holdings. Each holding line (a share class plus an owner, such as a trust or LLC) carries its last reported balance forward. Entities first reported during the period start at zero, so transfers between an insider's own trusts don't count as selling. Lines not reported for three years or more are listed separately and left out of totals.

Sales. A sale counts as under a 10b5-1 plan if its footnote cites one or the filing's Rule 10b5-1 box is checked, and as tax-related if its footnote cites tax obligations or sell-to-cover. Shares withheld by the company for taxes are listed separately. Sales with neither attribute are labeled "no plan disclosed".

Full methodology

Former or inactive filers (14)No filing in 18 months; last reported balances, not in any total

Name	Last filed	Last reported balance
Alessandrea Quane	Dec 9, 2024	507,073 shares, last reported balance as of Dec 6, 2024
Ranmali Bopitiya	Dec 3, 2024	241,488 shares, last reported balance as of Dec 2, 2024
Steven Wolin	Dec 3, 2024	102,598 shares, last reported balance as of Dec 2, 2024
Alphabet Inc.	Aug 21, 2023	17,542,864 shares, last reported balance as of Aug 17, 2023
Dennis Weaver	Dec 5, 2022	27,110 shares, last reported balance as of Dec 2, 2022
Charles Phillips Jr.	Oct 18, 2022	85,787 shares, last reported balance as of Jun 9, 2022
Meghan Joyce	Mar 3, 2022	58,966 shares, last reported balance as of Mar 2, 2022
Joel Klein	Aug 20, 2021	17 shares, last reported balance as of Aug 18, 2021
Ari Fischel	Mar 5, 2021	No balance on record
Teri List	Mar 5, 2021	50,000 shares, last reported balance as of Mar 5, 2021
Peter Thiel	Mar 3, 2021	21,601,879 shares, last reported balance as of Mar 3, 2021
General Catalyst Group Management, LLC	Mar 3, 2021	14,464,995 shares, last reported balance as of Mar 3, 2021
General Catalyst Group VI, L.P.	Mar 3, 2021	14,464,995 shares, last reported balance as of Mar 3, 2021
Joel Cutler	Mar 3, 2021	14,464,995 shares, last reported balance as of Mar 3, 2021

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