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Oluyemi Okupe

Chief Financial Officer

Officer

Latest: Hims & Hers Health, Inc. CFO selling · June 2026

21 filings analyzed · 1 company · Latest 2026-06-23

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Companies

Company Buys Sells Direction
Hims & Hers Health, Inc. HIMS 0 21 Net selling

Activity

June 2026
2026-06-23 Hims & Hers Health, Inc. HIMS 10b5-1 Plan
medium
Sell
18,197 shares
$619,217
Significance 5/10

CFO Oluyemi Okupe sold 18.2K shares of HIMS at $34.03 under 10b5-1 plan; holds 284.3K shares post-trade plus 109,524 options.

Oluyemi Okupe, CFO of Hims & Hers Health, Inc., sold 18,197 shares at $34.03 on 2026-06-22 as part of a pre-arranged 10b5-1 trading plan adopted on 2025-05-21, reducing his non-derivative holdings by 6.0% to 284,321 shares while retaining 109,524 shares in stock options. The transaction is scheduled rather than discretionary. His prior sales at this ticker show mixed outcomes: the 30-day change following this filing's scheduled execution occurs during a period when HIMS has gained 38.8% over the last 30 days, though the stock remains 53.2% below its 52-week high of $70.43. The company's latest quarter shows $608,104,000 in revenue and a net loss of $92,115,000, with annual revenue growth of +59.0% year-over-year, indicating growth amid current unprofitability.

April 2026
2026-04-22 Hims & Hers Health, Inc. HIMS 10b5-1 Plan
low
Sell
19,645 shares
$588,615
Significance 3/10

CFO Okupe Oluyemi sold 19,645 shares of HIMS at $29.96 under pre-arranged 10b5-1 plan; retains 262,954 shares.

Okupe Oluyemi, CFO of Hims & Hers Health, Inc., executed a sale of 19,645 shares at $29.96 on 2026-04-20 under a pre-arranged 10b5-1 trading plan adopted on 2025-05-21. This is a scheduled, non-discretionary transaction governed by the plan, so the timing reflects plan mechanics rather than active decision-making around current market conditions. Post-transaction, his holdings remain substantial at 262,954 shares, representing a -7.0% reduction from the prior level of 282,599 shares. The transaction reduced his position but did not exit the company; continued significant equity ownership by the CFO is an observable fact for investors assessing management stake alignment.

2026-04-20 Hims & Hers Health, Inc. HIMS 10b5-1 Plan
low
Sell
54,927 shares
$1,457,305
Significance 3/10

CFO Okupe Oluyemi sells 54,927 HIMS shares for $1,457,305.25 via scheduled 10b5-1 plan

Okupe Oluyemi, CFO of Hims & Hers Health, executed 2 separate sales totaling 54,927 shares for $1,457,305.25 across April 16–17, 2026, at prices ranging from $25.90 to $27.83 per share. This sale was conducted under a 10b5-1 trading plan adopted on 2025-05-21, meaning the transactions were scheduled in advance rather than discretionary. Post-transaction, Oluyemi held 270,046 shares, representing a 16.9% reduction from the prior holding of 324,973 shares. As a scheduled plan execution, the sale reflects predetermined liquidity or portfolio management rather than a real-time response to company developments or market conditions.

December 2025
2025-12-23 Hims & Hers Health, Inc. HIMS 10b5-1 Plan
low
Sell
23,090 shares
$824,710
Significance 3/10

CFO Okupe Oluyemi sold 23,090 shares of HIMS at $35.72 under pre-arranged 10b5-1 plan

Okupe Oluyemi, Chief Financial Officer of Hims & Hers Health, Inc., sold 23,090 shares at $35.72 on 2025-12-22, reducing his holdings from 117,423 shares to 94,333 shares. This transaction was executed under a 10b5-1 trading plan adopted on 2025-05-21, meaning the sale was scheduled in advance and not discretionary. The 19.7% reduction in holdings reflects a scheduled divestiture with no signal regarding current conviction or market outlook, as the timing and volume were determined months prior to execution.

November 2025
2025-11-19 Hims & Hers Health, Inc. HIMS 10b5-1 Plan
medium
Sell
23,187 shares
$853,490
Significance 5/10

HIMS CFO Okupe sells 23,187 shares (23.2K) at $36.81 under pre-arranged 10b5-1 plan; post-transaction holdings 70,232 shares

Okupe Oluyemi, HIMS Chief Financial Officer, executed a sale of 23,187 shares at $36.81 on 2025-11-17 under a 10b5-1 trading plan adopted on 2025-05-21, reducing his holdings from 93,419 shares to 70,232 shares. The transaction represents a 24.8% reduction in holdings and generated approximately $853,490.28. As a pre-arranged and scheduled transaction under Rule 10b5-1, this sale reflects contractual execution rather than a discretionary trade decision, and therefore does not convey timing-based market signals about insider confidence at this price.

October 2025
2025-10-20 Hims & Hers Health, Inc. HIMS 10b5-1 Plan
medium
Sell
11,592 shares
$662,222
Significance 6/10

CFO Oluyemi sold 11,592 shares of HIMS at $57.13; stock now at $51.36, -25.3% from 52-week high.

CFO Okupe Oluyemi sold 11,592 shares at $57.13 on 2025-10-17, reducing his holdings by 14.2% to 70,232 shares. The stock is currently trading at $51.36, down 11.2% over the prior 30 days and 25.3% below the 52-week high of $68.74, suggesting the sale occurred before a significant drawdown. However, this sale pattern requires context: Oluyemi executed five separate transactions at HIMS over the prior three weeks (2025-09-15 through 2025-10-17), with two recent trades yet to show measurable 30-day returns. His cross-ticker track record shows 20 prior sells with a 15.38% well-timed rate, though none of his prior HIMS sales have yet registered a well-timed outcome at the 90-day mark (0 of 0). Notably, HIMS fundamentals remain strong with $544.8M quarterly revenue, +69.3% annual growth, and $42.5M net income, though the P/E of 88.55 reflects elevated valuation. The repeated sales within a compressed timeframe merit observation against the company's growth metrics.

2025-10-07 Hims & Hers Health, Inc. HIMS 10b5-1 Plan
medium
Sell
11,595 shares
$669,232
Significance 5/10

CFO Okupe Oluyemi sold 11,595 shares of HIMS at $57.72 on 2025-10-03, reducing holdings by 14.2%.

CFO Okupe Oluyemi executed a sale of 11,595 shares at $57.72 on 2025-10-03, reducing his position from 81,827 shares to 70,232 shares. The timing context is notable: HIMS has appreciated +19.8% over the prior 30 days and +13.1% over 90 days, yet trades at $57.97 currently—15.7% below its 52-week high of $68.74. The SAME-TICKER HISTORY reveals a concentrated selling pattern: four sales between 2025-08-26 and 2025-09-29 immediately prior to this transaction, with only one measurable outcome (30d: +25.6% from the 2025-08-26 sale). His cross-ticker track record shows avg 90d returns of +47.0% after sells with a 15.38% well-timed rate, suggesting his prior sells have generally preceded stock gains rather than declines. Against strong near-term momentum and a portfolio of fundamentals showing +69.3% annual revenue growth and positive net income of $42,505,000.00, the series of incremental sales warrants attention to whether this reflects deliberate portfolio management or a shift in conviction toward the position.

September 2025
2025-09-30 Hims & Hers Health, Inc. HIMS 10b5-1 Plan
medium
Sell
85,000 shares
$5,116,924
Significance 4/10

CFO Okupe Oluyemi sold 85,000 shares (85.0K) of HIMS at $60.20 for $5.1M under pre-arranged 10b5-1 plan

Okupe Oluyemi, Chief Financial Officer of Hims & Hers Health, Inc., executed a sale of 85,000 shares (85.0K shares) on 2025-09-29 under a pre-arranged 10b5-1 trading plan adopted on 2025-05-21, reducing his holdings by 54.8% from 155,232 shares to 70,232 shares. This is a scheduled transaction rather than a discretionary trade, eliminating timing-based interpretation. The 70,232 shares (70.2K) remaining represent a material ongoing stake but a substantial reduction in exposure relative to his prior position.

2025-09-24 Hims & Hers Health, Inc. HIMS 10b5-1 Plan
medium
Sell
23,584 shares
$1,361,766
Significance 5/10

CFO Okupe Oluyemi sold 23.6K HIMS shares at $57.74; stock now -22.5% from 52-week high at $53.25

CFO Okupe Oluyemi sold 23,584 shares at $57.74 on 2025-09-22, reducing holdings by -18.3% from 129.0K to 105.4K shares, for a total value of $1,361,766.10. The sale occurred near a recent intra-period peak: the stock has since fallen to $53.25, down -22.5% from its 52-week high of $68.74, though it remains +23.9% higher over the past 30 days. At the cross-ticker level, Okupe's 20 prior sells across all holdings show a well-timed rate of 14.29%, suggesting mixed timing; however, at HIMS specifically, his 5 prior trades show 0 well-timed outcomes at the 90-day mark. The company reports strong fundamentals with $544.8M revenue (+69.3% annual growth) and $42.5M net income, though the elevated P/E of 91.81 reflects high valuation expectations. This sale follows two other HIMS sales on 2025-09-15 and comes amid ongoing stock strength, warranting monitoring of whether this marks a pattern of management liquidity or a signal of valuation concerns.

2025-09-17 Hims & Hers Health, Inc. HIMS 10b5-1 Plan
medium
Sell
145,000 shares
$8,026,076
Significance 5/10

Hims CFO Okupe Oluyemi sells 145,000 shares ($8.0M) via scheduled 10b5-1 plan adopted May 21

Okupe Oluyemi, Hims' CFO, executed 2 separate sales on September 15, totaling 145,000 shares for $8,026,075.61 at a blended average price of $55.35. The transaction reduced his holdings by 52.9%, from 273,984 shares to 128,984 shares post-transaction. This sale was conducted under a pre-arranged 10b5-1 trading plan adopted on May 21, 2025, making it a scheduled transaction rather than a discretionary decision. The magnitude of the position reduction—more than half of his prior holdings—and the material dollar amount warrant monitoring, though the scheduled nature of the plan limits inference about current sentiment toward the company.

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