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Oscar Health (OSCR) CEO exercises 5.7M PSUs and buys 1M shares in April transactions

Filing Impact
(Very High)
Filing Sentiment
(Very Positive)
Form Type
4

Rhea-AI Filing Summary

Oscar Health, Inc. Chief Executive Officer Mark T. Bertolini reported equity compensation activity and a share purchase. On April 3, 2026, performance stock units covering 5,733,334 shares vested and were exercised at $0.00, delivering the same number of Class A shares based on stock price targets.

On April 6, 2026, the company withheld 1,000,001 Class A shares at $11.92 per share to satisfy tax obligations on a portion of the vested PSUs. That same day, Bertolini purchased 1,000,000 Class A shares from the issuer in a private placement at $11.92 per share. Following these transactions, he directly holds 10,196,876 Class A shares. Future settlements of remaining PSUs and related tax-covering sales will occur under a pre-arranged Rule 10b5-1 instruction letter.

Positive

  • None.

Negative

  • None.
Insider Bertolini Mark T
Role Chief Executive Officer
Bought 1,000,000 shs ($11.92M)
Type Security Shares Price Value
Tax Withholding Class A Common Stock 1,000,001 $11.92 $11.92M
Purchase Class A Common Stock 1,000,000 $11.92 $11.92M
Exercise Performance Restricted Stock Units 5,733,334 $0.00 --
Exercise Class A Common Stock 5,733,334 $0.00 --
Holdings After Transaction: Class A Common Stock — 9,196,876 shares (Direct); Performance Restricted Stock Units — 0 shares (Direct)
Footnotes (1)
  1. Represents performance stock units (PSUs) that vested based on achievement of specified price per share targets. Each PSU represents a contingent right to receive one share of Class A common stock. Includes shares to be issued in connection with the vesting of one or more restricted stock units. Represents shares withheld by the issuer to satisfy tax obligations with respect to the portion of PSUs settled on April 6, 2026. Settlement of the remaining PSUs and the restricted stock units that vested on April 3, 2026, and sales to cover the resulting tax obligations, will occur at a later date in accordance with a 10b5-1 instruction letter entered into by the reporting person on November 10, 2025, as amended and restated on March 24, 2026. Represents shares of Class A common stock purchased from the issuer by the reporting person in a private placement transaction.
PSUs exercised 5,733,334 shares Performance stock units vesting into Class A common stock on April 3, 2026
Tax-withheld shares 1,000,001 shares at $11.92 Shares withheld by issuer to satisfy tax obligations on April 6, 2026
Private placement purchase 1,000,000 shares at $11.92 Class A shares purchased from issuer by CEO on April 6, 2026
Post-transaction holdings 10,196,876 shares Direct Class A holdings following reported transactions
PSU exercise price $0.00 per share Conversion of performance stock units into Class A common stock
Performance Restricted Stock Units financial
"security_title: "Performance Restricted Stock Units" tied to PSUs that vested"
Performance restricted stock units (PRSUs) are promises to deliver company shares to employees or executives only if the business meets specific performance targets and any time-based holding rules. Think of them as a bonus that converts into stock only after set goals are reached, so investors watch PRSUs for two reasons: they can dilute existing shares if paid out, and they signal how closely management’s pay is tied to company performance.
performance stock units (PSUs) financial
"Represents performance stock units (PSUs) that vested based on achievement of specified price per share targets."
Performance stock units (PSUs) are a form of executive or employee pay that promise company shares only if pre-set performance goals are met over a defined period; think of them as a bonus paid in stock that arrives only when the company hits agreed targets. Investors watch PSUs because they affect the number of shares outstanding (dilution) and reveal how management’s pay is tied to financial or operational results, aligning incentives with shareholder outcomes.
Rule 10b5-1 instruction letter regulatory
"will occur at a later date in accordance with a 10b5-1 instruction letter entered into by the reporting person"
private placement transaction financial
"Represents shares of Class A common stock purchased from the issuer by the reporting person in a private placement transaction."
tax obligations financial
"Represents shares withheld by the issuer to satisfy tax obligations with respect to the portion of PSUs settled on April 6, 2026."
Form 4 Insider Transactions: What Each Field Means →
SEC Form 4
FORM 4UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940
OMB APPROVAL
OMB Number:3235-0287
Estimated average burden
hours per response:0.5
Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).
Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.
1. Name and Address of Reporting Person*
Bertolini Mark T
(Last)(First)(Middle)
75 VARICK STREET, 5TH FLOOR
(Street)
NEW YORK NEW YORK 10013
(City)(State)(Zip)
UNITED STATES
(Country)		2. Issuer Name and Ticker or Trading Symbol
Oscar Health, Inc. [ OSCR ] 		5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)
XDirector10% Owner
XOfficer (give title below)Other (specify below)
Chief Executive Officer
2a. Foreign Trading Symbol
3. Date of Earliest Transaction (Month/Day/Year)
04/03/2026		6. Individual or Joint/Group Filing (Check Applicable Line)
XForm filed by One Reporting Person
Form filed by More than One Reporting Person
4. If Amendment, Date of Original Filed (Month/Day/Year)

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3) 2. Transaction Date (Month/Day/Year)2A. Deemed Execution Date, if any (Month/Day/Year)3. Transaction Code (Instr. 8) 4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5) 5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4) 6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4) 7. Nature of Indirect Beneficial Ownership (Instr. 4)
CodeVAmount(A) or (D)Price
Class A Common Stock04/03/2026M5,733,334(1)A(2)10,196,877(3)D
Class A Common Stock04/06/2026F1,000,001(4)D$11.929,196,876(3)D
Class A Common Stock04/06/2026P1,000,000(5)A$11.9210,196,876(3)D
Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned
(e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3) 2. Conversion or Exercise Price of Derivative Security 3. Transaction Date (Month/Day/Year)3A. Deemed Execution Date, if any (Month/Day/Year)4. Transaction Code (Instr. 8) 5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5) 6. Date Exercisable and Expiration Date (Month/Day/Year)7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4) 8. Price of Derivative Security (Instr. 5) 9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4) 10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4) 11. Nature of Indirect Beneficial Ownership (Instr. 4)
CodeV(A)(D)Date ExercisableExpiration DateTitleAmount or Number of Shares
Performance Restricted Stock Units(2)04/03/2026M5,733,334 (1) (1)Class A Common Stock5,733,334$00D
Explanation of Responses:
1. Represents performance stock units (PSUs) that vested based on achievement of specified price per share targets.
2. Each PSU represents a contingent right to receive one share of Class A common stock.
3. Includes shares to be issued in connection with the vesting of one or more restricted stock units.
4. Represents shares withheld by the issuer to satisfy tax obligations with respect to the portion of PSUs settled on April 6, 2026. Settlement of the remaining PSUs and the restricted stock units that vested on April 3, 2026, and sales to cover the resulting tax obligations, will occur at a later date in accordance with a 10b5-1 instruction letter entered into by the reporting person on November 10, 2025, as amended and restated on March 24, 2026.
5. Represents shares of Class A common stock purchased from the issuer by the reporting person in a private placement transaction.
Remarks:
/s/ Melissa Curtin, Attorney-in-Fact04/07/2026
** Signature of Reporting PersonDate
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.
* Form 4: SEC 1474 (03-26)

Source: View Original Filing on SEC EDGAR

FAQ

What insider transactions did Oscar Health (OSCR) report for CEO Mark Bertolini?

Oscar Health reported that CEO Mark Bertolini exercised performance stock units into 5,733,334 Class A shares, had 1,000,001 shares withheld for taxes, and purchased 1,000,000 additional Class A shares in a private placement, all in early April 2026.

How many Oscar Health (OSCR) shares does CEO Mark Bertolini hold after these Form 4 transactions?

After the reported transactions, CEO Mark Bertolini directly holds 10,196,876 shares of Oscar Health Class A common stock. This reflects PSU vesting, tax-withholding by the issuer, and his purchase of 1,000,000 shares in a private placement at $11.92 per share.

What price did Oscar Health (OSCR) CEO Mark Bertolini pay for newly purchased shares?

Mark Bertolini purchased 1,000,000 Oscar Health Class A shares at $11.92 per share in a private placement with the issuer. The same $11.92 per share price was used to value 1,000,001 shares withheld by the company to satisfy tax obligations on vested performance stock units.

How were Oscar Health (OSCR) performance stock units treated in this Form 4 filing?

Performance stock units representing 5,733,334 shares vested based on specified stock price targets and were exercised at $0.00, delivering an equal number of Class A shares. A portion of the resulting shares was withheld to cover tax obligations, with further PSU settlements scheduled later under a Rule 10b5-1 plan.

Were Oscar Health (OSCR) CEO share dispositions open-market sales?

The reported share disposition was not an open-market sale. Instead, 1,000,001 Class A shares were withheld by Oscar Health to satisfy tax obligations on vested performance stock units. Future sales to cover taxes will follow a pre-arranged Rule 10b5-1 instruction letter entered into by Bertolini.

What is the role of a Rule 10b5-1 instruction letter in Oscar Health (OSCR) CEO transactions?

The Rule 10b5-1 instruction letter governs future settlements of remaining performance stock units and related tax-covering share sales. It sets a predefined trading plan, meaning upcoming transactions for these awards will follow established instructions rather than discretionary timing decisions by CEO Mark Bertolini.