Okupe Oluyemi, Chief Financial Officer of Hims & Hers Health (HIMS), has been a consistent seller of the company’s stock through the second half of 2026. Across 70 total filings, Oluyemi has executed no open-market purchases and has sold $27.6 million worth of shares. The most recent activity, spanning June through September 2026, shows a steady cadence of open-market sales, with the largest single transaction on June 18 totaling $1.94 million. Other sales include $876,846 on September 22, $619,216 on June 22, and $354,860 on September 17.
The pattern is dominated by option exercises paired with same-day sales, a common structure for executives converting vested equity into cash. For example, on September 22, Oluyemi exercised options valued at $70,140 and sold $876,846 in the same transaction. Similar pairings appear on August 19, August 17, July 17, and July 6, with exercise values ranging from $24,739 to $47,033 against sale values between $148,111 and $261,802. These are not discretionary purchases; the exercise code "M" is mechanical, and the sales are the only cash-generating leg of the transaction.
The data also includes tax-withholding events coded "F," such as $1.03 million on August 14 and $1.19 million on June 15, where shares were automatically withheld to cover tax obligations. These are not decisions to sell but standard settlements of equity grants. The overall direction is unambiguous: every discretionary transaction is a sale, with no buys in the entire filing history. The dollar values are substantial, and the frequency has been steady, but the structure points to routine equity compensation management rather than a concentrated bet against the stock.
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