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Oscar Health, Inc.·4

Apr 7, 4:16 PM ET

Bertolini Mark T 4

Research Summary

AI-generated summary

Updated

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.