Bertolini Mark T 4

4 · Oscar Health, Inc. · Filed Apr 7, 2026

AI-generated summary of this filing

Updated Apr 7, 2026

Oscar Health (OSCR) CEO Mark Bertolini Exercises PSUs and Buys Shares

What Happened

Mark T. Bertolini, CEO of Oscar Health (OSCR), had performance stock units (PSUs) vest and converted those PSUs into common shares (5,733,334 shares). As part of the settlement, 1,000,001 shares were withheld to cover tax obligations (value $11,920,012). Separately, on April 6, 2026 he purchased 1,000,000 shares directly from the issuer in a private placement at $11.92 per share for $11,920,000.

Key Details

Transaction dates and prices:
- April 3, 2026: Exercise/conversion of 5,733,334 PSUs into shares (derivative settlement).
- April 6, 2026: 1,000,001 shares withheld to satisfy taxes at $11.92/share (tax withholding sale — $11,920,012).
- April 6, 2026: Private purchase of 1,000,000 shares at $11.92/share ($11,920,000).
Shares owned after transaction: Not specified in the provided filing excerpt.
Footnotes of note:
- The shares originated from PSUs that vested based on specified price targets (F1–F3).
- The 1,000,001-share withholding satisfied tax obligations for the portion of PSUs settled on April 6; remaining PSUs and RSUs vested April 3 will be settled and tax-covered later per a 10b5-1 instruction letter (entered Nov 10, 2025; amended Mar 24, 2026) (F4).
- The 1,000,000-share purchase was a private placement from the issuer (F5).
Filing timeliness: Report filed April 7, 2026 for transactions on April 3 and April 6 — no indication in the filing excerpt that it was late.

Context

This was largely a PSU settlement (an award converting to shares) with routine tax-withholding via share retention/sale; those withheld shares are not a market-sale signal of bearishness but a tax-related disposition.
The separate private purchase of 1,000,000 shares for ~$11.92M is a direct purchase from the company and represents an affirmative acquisition by the CEO (a meaningful monetary commitment).
For retail investors: PSU vesting and planned tax withholdings are common and procedural; the notable item to watch is the private purchase, which is a clear insider buy rather than an internal tax-driven sale.

Form 4

Period: 2026-04-03

DirectorChief Executive Officer

Transactions

Exercise/Conversion
Class A Common Stock
[F1][F2][F3]
2026-04-03+5,733,334→ 10,196,877 total
Tax Payment
Class A Common Stock
[F4][F3]
2026-04-06$11.92/sh−1,000,001$11,920,012→ 9,196,876 total
Purchase
Class A Common Stock
[F5][F3]
2026-04-06$11.92/sh+1,000,000$11,920,000→ 10,196,876 total
Exercise/Conversion
Performance Restricted Stock Units
[F2][F1]
2026-04-03−5,733,334→ 0 total
→ Class A Common Stock (5,733,334 underlying)

Footnotes (5)

[F1]Represents performance stock units (PSUs) that vested based on achievement of specified price per share targets.
[F2]Each PSU represents a contingent right to receive one share of Class A common stock.
[F3]Includes shares to be issued in connection with the vesting of one or more restricted stock units.
[F4]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.
[F5]Represents shares of Class A common stock purchased from the issuer by the reporting person in a private placement transaction.

Signature

/s/ Melissa Curtin, Attorney-in-Fact|2026-04-07

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