DOCN DigitalOcean Holdings, Inc. Insider Trading

CFO Matt Steinfort sold 10,000 DOCN shares at $170.07; pre-arranged 10b5-1 plan, routine position management

Matt Steinfort, CFO of DigitalOcean, sold 10,000 shares (10.0K shares) at $170.07 on 2026-06-02 under a pre-arranged 10b5-1 trading plan, reducing his holdings from 548,414 to 538,414 shares. The sale is scheduled, not discretionary, meaning it reflects a pre-determined execution plan rather than a contemporaneous market decision. Steinfort's prior sales at DigitalOcean produced mixed outcomes: a May 2026 sale saw 30-day and 90-day returns of +13.5% each, while a March 2026 sale yielded +62.5% over 30 days and +213.1% over 90 days, indicating the stock has generally moved upward following his prior exits at this ticker. The company maintains solid fundamentals with $257,905,000.00 in quarterly revenue, +15.5% annual growth, and a $18,125,970,956.08 market cap, though the P/E of 76.51 reflects elevated valuation relative to earnings.

Director Warren Jenson sold 20,000 shares of DOCN at $147.62; holds 32,497 post-sale. Stock up 67.2% in 30 days, 148.9% in 90 days.

Warren Jenson, a Director at DigitalOcean, sold 20,000 shares (representing a -38.1% reduction in holdings) on 2026-05-19 at $147.62, raising $2,952,400.00 in total proceeds. The sale occurred as DOCN has appreciated substantially—up 67.2% over 30 days and 148.9% over 90 days—though the stock currently trades at $158.35, approximately 3.9% below its 52-week high of $164.77. With a P/E of 69.76 and recent quarterly revenue of $257,905,000.00 alongside a net income of $15,771,000.00, the company shows fundamentals supporting growth at +15.5% annual revenue expansion. Jenson has only 1 prior buy on record in his cross-ticker transaction history, providing limited baseline for assessing transaction patterns. The substantial reduction in his position stake—from 52,497 to 32,497 shares—during a period of marked stock appreciation warrants investor scrutiny of broader market conditions and company-specific context at the time of execution.

CFO Matt Steinfort sold 25,000 DOCN shares at $152.50 on 2026-05-15; stock now $150.02, still +75.2% over 30 days.

Matt Steinfort, DigitalOcean's CFO, sold 25,000 shares (representing -4.2% of his pre-transaction holdings) at $152.50, generating $3,812,500.00 in proceeds. The stock has momentum—up 75.2% over the past 30 days and up 117.9% over 90 days—yet is trading -9.0% below the 52-week high of $164.77 at the current price of $150.02. Notably, Steinfort's only prior sale at DOCN (on 2026-03-03) saw the stock appreciate 166.1% over the following 90 days, and his cross-ticker track record of 1 prior sell shows a 0.00% well-timed rate, meaning prior sells occurred before gains. The substantial recent rally and the CFO's exit during a strong uptrend, combined with the absence of any well-timed sale pattern, warrant observer attention to whether the sale signals a tactical window or reflects underlying valuation constraints.

Access Industries (10% owner) sells 3,300,000 shares for $495,990,000.00; post-transaction holdings drop to 119,587 shares (-96.5%)

Access Industries, a 10% stakeholder in DigitalOcean, executed two separate open-market sales totaling 3,300,000 shares (3.30M shares) at $150.30 on 2026-05-13 for $495,990,000.00. This sale reduces the firm's DOCN position from 3,419,587 shares to 119,587 shares, a -96.5% reduction that effectively exits the investor's substantial ownership stake. The timing occurs as the stock trades at $154.87, roughly 99.3% above its 30-day low and 127.2% above its 90-day low, suggesting the transaction completed near elevated valuations in a strong recent price environment. Access Industries' cross-ticker track record shows a 90-day well-timed rate of 25.00% (prior sells, where positive returns = poorly timed), but at DOCN specifically, the insider's 5 prior trades show mixed execution: only 2 of 5 prior sales achieved negative 90-day returns. The decision to liquidate nearly the entire position warrant attention to whether this signals a structural reassessment of the investment thesis.

Access Industries (10% owner) sold 391,806 shares in 18 transactions for $60,782,792.16 on 2026-05-07 to 2026-05-11.

Access Industries, a 10% institutional holder of DigitalOcean, executed 18 separate sales totaling 391,806 shares for $60,782,792.16 across two trading dates (May 7–11, 2026), reducing holdings by 1.8% to 21,657,187 shares post-transaction. The blended average transaction price was $155.13, with prices ranging from $147.80 to $162.51 across the distributed sell program. The insider's cross-ticker track record shows only 2 prior open-market sells historically, and prior DOCN trades (June 2025) do not yet have measurable 90-day outcomes. DigitalOcean's fundamentals show $257,905,000 in latest-quarter revenue and +15.5% annual revenue growth, but the large scale and mechanical nature of this multi-tranche liquidation—reducing a 22.05M-share position methodically over two days—warrants examination of whether strategic, operational, or fund-level factors are driving the disposition.

CFO Matt Steinfort sold 20,000 shares of DOCN at $55.40 (-3.5% of holdings); stock at -19.6% from 52-week high.

Matt Steinfort, CFO of DigitalOcean, sold 20,000 shares for $1,108,000.00, reducing his holdings from 565,916 shares to 545,916 shares. The sale occurred at $55.40, which is -19.6% from the 52-week high of $68.86, and the stock has gained 20.7% over the trailing 90 days. DigitalOcean's recent quarter showed strong fundamentals: $229.6M in revenue with $158.4M net income, 15.5% annual revenue growth, and a P/E of 11.94 on a $5.1B market cap. The CFO's modest disposition (3.5% reduction in holdings) during a period of near-term strength and reasonable valuation warrants standard monitoring but lacks indicators of acute concern.

DOCN Chief Accounting Officer sold 22,000 shares at $54.77; holding reduced to 62,469 shares (-26.0%)

Barrett Cherie, the Chief Accounting Officer of DigitalOcean, sold 22,000 shares (62.5K shares remaining) at $54.77 on 2026-03-02 for $1,204,940.00. The sale represents a -26.0% reduction in her pre-transaction holdings, a material reallocation at a price 1.1% below the current market price of $55.40. DigitalOcean is trading -19.6% from its 52-week high of $68.86, with solid fundamentals showing $229.6M revenue, $158.4M net income, and 15.5% annual revenue growth at an attractive 11.94 P/E. The timing of the sale—when the stock is well off its peak but still up 20.7% over 90 days—warrants attention to whether the sale reflects portfolio adjustment decisions or tactical views about near-term valuation.

Access Industries Holdings LLC sells 3,496,504 shares for $100,000,014.40; post-transaction holdings drop to 140,599 shares

Access Industries Holdings LLC, a 10% owner, executed 2 separate sales on 2025-06-04 totaling 3,496,504 shares (3.50M shares) for $100,000,014.40 at a blended average price of $28.60. The filer's holdings fell from 3,637,103 shares (3.64M shares) pre-transaction to 140,599 shares (140.6K shares) post-transaction, representing a net reduction of 3,496,504 shares or -96.1% of pre-transaction holdings. This constitutes a near-complete exit from the position by a major shareholder in a single trading session.

DOCN Chief Product & Tech Officer sells 41,541 shares at $29.49 (now $30.07); -27.6% over 90 days post-prior sales

Saha Bratin sold 41,541 shares of DigitalOcean for $1,225,044.09 on 2025-06-03, reducing holdings by 12.1% from 343.1K to 301.6K shares. The stock has declined 27.6% over the past 90 days and sits 35.6% below its 52-week high of $46.69. At DOCN specifically, Bratin's two prior sales (2024-11-19 and 2024-11-18) were followed by positive 90-day returns of 23.7% and 20.8% respectively, indicating neither was well-timed at the 90-day mark. The broader timing pattern across all his cross-ticker sales (0.00% well-timed rate) does not support that this sale occurs in advance of further declines, though the recent 90-day price action suggests significant recent weakness in the name.

DOCN Chief Product & Tech Officer Saha Bratin sold 20,457 shares for $750.8K across 2 transactions (Nov 18-19)

Saha Bratin executed two separate sales totaling 20,457 shares for $750,823.29, reducing holdings from 407,285 to 386,828 shares (-5.0%). The blended average sale price of $36.70 sits below the current price of $38.02, and the stock has declined 12.2% over 30 days despite posting +20.2% annual revenue growth and a profitable $32.9M net income last quarter. The sale volume is material but represents a modest reduction in a substantial 386.8K-share post-transaction position. No scheduling or plan flags are noted in the filing, indicating these were discretionary open-market sales, though the modest percentage reduction and the executive's continued significant ownership stake limit any inference about confidence shifts.