Hims & Hers (HIMS) CFO Okupe Oluyemi Exercises Options, Sells Shares

What Happened

• Okupe Oluyemi, Chief Financial Officer of Hims & Hers (HIMS), reported multiple option/RSU settlements and share disposals between June and August 2026. Key cash sales: 55,383 shares sold on 2026-06-18 at an average $35.09 for $1,943,389, and 9,388 shares sold on 2026-08-17 at $27.89 for $261,802 (total cash proceeds ≈ $2,205,191).
• Oluyemi also acquired shares through exercises/vestings: 71,616 shares were reported acquired on 2026-08-14 (conversion/vesting, price N/A) and 9,388 shares were acquired on 2026-08-17 by exercising options at $5.01 (cost $47,034). To cover tax withholding on RSU settlements, 36,437 shares were withheld on 2026-08-14 (reported at $28.15, value $1,025,702).
• Overall the filing shows roughly 81,004 shares acquired via exercise/vesting and ~182,212 shares disposed (including sales and shares withheld/zero-price conversions). Sales are routine here and many transactions were pre-arranged under a 10b5-1 plan.

Key Details

• Transaction dates/prices:
  • 2026-06-18: Open-market sale 55,383 shares @ avg $35.09 = $1,943,389 (price range $34.95–$35.36; F2).
  • 2026-08-14: Conversion/vesting of 71,616 shares (price N/A); 36,437 shares withheld for taxes @ $28.15 = $1,025,702 (F3, F4).
  • 2026-08-14: Several RSU/derivative conversions reported at $0 (18,335; 22,988; 11,482; 18,811 shares) — these reflect vesting/settlement, not open-market sales.
  • 2026-08-17: Exercised options for 9,388 shares @ $5.01 (paid $47,034) and immediately sold 9,388 shares @ $27.89 = $261,802.
• Shares owned after transactions: The filing does not disclose the resulting total beneficial ownership figure in the information you provided.
• Notable footnotes: Transactions were effected pursuant to a Rule 10b5-1 trading plan adopted May 21, 2025 (F1). RSUs represent contingent rights to shares and many are subject to multi-year vesting schedules (F3–F9). One stock option award reported as fully vested (F10).
• Timeliness: The report covers transactions beginning 2026-06-18 but was filed 2026-08-18, indicating a delayed filing for at least some entries.

Context

• Many of the derivative entries are option exercises or RSU vestings (transaction code M). Zero-dollar disposals indicate share settlement/withholding rather than a market sale; in particular, shares were withheld to satisfy tax withholding obligations (transaction code F).
• The 9,388-share option exercise followed by an immediate sale is effectively a cashless exercise/sale — common for covering exercise costs or diversifying, and less indicative of directional insider sentiment.
• The 10b5-1 plan means some exercises/sales were pre-scheduled, which reduces (but does not eliminate) implications about timing or insider intent.

Bottom line: HIMS' CFO converted/received a large block of shares via exercises and RSU vesting, sold roughly 64.8k shares in open-market transactions for about $2.21M, and had 36.4k shares withheld to cover taxes ($1.03M). The trades were partly conducted under a pre-arranged 10b5-1 plan.