DOCU DOCUSIGN, INC. Insider Trading

CEO Thygesen sells 26,250 shares of DOCU for $1,254,161 (blended avg $47.78); holds 152,237 post-transaction

CEO Allan C. Thygesen executed 3 separate sales totaling 26,250 shares for $1,254,161.00 on April 1, 2026 at prices ranging from $46.44 to $48.12, reducing his holdings by 14.7%. The sales occur against a backdrop where DOCU trades at $48.37 current price, down 48.4% from its 52-week high of $93.84 but up 3.5% over the prior 30 days and down 25.4% over 90 days. His prior trades at DOCU (5 distinct transactions in the same-ticker history) show a 90-day well-timed rate of 2 of 2 measurable outcomes, suggesting pattern consistency, though the most recent 3 sales from January 2026 remain unmeasurable in their 90-day outcome. At the cross-ticker level, Thygesen's historical 90-day well-timed rate across all open-market sells stands at 58.82% with a modest +0.6% average 90-day return, indicating neither exceptional foresight nor a strong positive signal. The company's fundamentals remain solid: $818.4M quarterly revenue, +8.2% annual revenue growth, $83.7M net income, and a P/E of 31.61 in a $9.4B market-cap business.

DocuSign CLO Shaughnessy sold 12,000 shares (−18.3% of holdings) in 3 transactions for $562.0K; 5 of 5 prior DOCU sales were well-timed at 90d.

Shaughnessy James P executed 3 separate sales totaling 12,000 shares for $562,011.91 on 2026-04-01, reducing his holdings from 65,631 to 53,631 shares. His historical trading pattern at DocuSign is notable: all 5 prior trades at DOCU were well-timed, with 90-day post-sale declines ranging from −26.0% to −29.3%, indicating consistent ability to sell before downturns at this ticker. The current stock price of $48.37 is −48.4% from the 52-week high of $93.84, suggesting material price deterioration since those prior well-timed sales. The blended sale price of $46.83 sits below current price, meaning this transaction occurred during a modest rally (+3.5% over 30 days), yet within the broader −25.4% 90-day decline context. The combination of substantial position reduction (−18.3%), historical pattern of well-timed exits at this specific ticker, and current deep drawdown from peak warrants close attention to whether this sale continues a pattern of prescient timing or signals changing conviction about DocuSign's trajectory.

Chatwani (President General Mgr, Growth) sells 16,696 shares for $803,042.91; prior 5 DOCU trades perfectly timed (5/5 well-timed at 90d).

Chatwani executed 5 separate sales totaling 16,696 shares at prices ranging from $45.52 to $49.50, reducing holdings by 18.7% from 89,154 to 72,458 shares. His prior 5 trades at DOCU show a perfect timing pattern: all 5 previous sales were well-timed at the 90-day mark, with negative 90-day returns ranging from -18.5% to -33.6%, indicating he has consistently sold ahead of declines at this specific ticker. The stock is currently -49.1% from its 52-week high of $93.84, down -31.8% over 90 days, placing this sale in a context where the company remains profitable with $83.7M in net income but has experienced material recent weakness. The alignment between his demonstrated timing accuracy at DOCU and the present execution warrants attention to whether similar post-sale price action materializes.

DocuSign CEO Thygesen sells 26,250 shares for $1.8M at $69.60 avg; stock down -34.0% from 52-week high.

Thygesen executed 3 separate sales totaling 26,250 shares for $1,827,054.87 on 2026-01-09, reducing his holdings by 15.6% from 168,511 to 142,261 shares. The sales occurred at an average blended price of $69.60, though the current stock price is $64.51—roughly 7.3% below the transaction prices. DocuSign's stock has declined 34.0% from its 52-week high of $97.70 and 9.3% over the past 30 days, suggesting significant downward momentum at the time of and after this sale. Notably, Thygesen's prior 5 sales at DOCU show mixed timing results: 3 of the 5 prior transactions (60%) were followed by negative 90-day returns, indicating some pattern of selling before subsequent declines. However, the current stock price trading below the sale prices and the steep ytd decline merit close investor attention to underlying operational or market conditions.

CLO Shaughnessy sells 12,000 DOCU shares across 4 transactions for $804,392.16 at avg $67.03

Shaughnessy James P, Chief Legal Officer of DocuSign, executed 4 separate sales totaling 12,000 shares for $804,392.16 on 2026-01-02, at a blended average price of $67.03, reducing holdings from 66,550 to 54,550 shares (-18.0%). The transaction occurred near the stock's 52-week low range, with DOCU trading at $65.19 (current price) and down 33.3% from its 52-week high of $97.70. Across his cross-ticker track record, this insider has achieved a 90-day well-timed rate of 69.23% on 13 prior sells; however, at this specific ticker (DOCU), 3 of 5 prior sales were well-timed at the 90-day mark, with recent October 2025 sales showing near-term gains (+2.5% to +3.4% at 30 days). The company maintains fundamental solidity with $818.4M in latest quarterly revenue, $83.7M net income, and 7.8% annual revenue growth, though trading at a 43.17 P/E ratio. The scale and timing of this liquidation warrant monitoring against near-term stock performance and executive commentary.

CFO Grayson Blake Jeffrey sells 9,515 shares (9.5K) at blended avg $68.33; stock down -31.0% from 52-week high.

Grayson Blake Jeffrey, DocuSign's CFO, executed 2 separate sales on 2025-12-17 totaling 9,515 shares for $650,180.40 at prices of $67.86 and $68.61, reducing his holdings by 7.4% to 118,213 shares. The sale occurs with the stock trading $67.79, down 31.0% from its 52-week high of $98.17 and down 20.3% over the past 90 days, suggesting the CFO is executing sales during a period of significant weakness. His prior 5 trades at DocuSign show a 2-of-5 well-timed pattern at the 90-day mark, with the most recent September and July 2025 sales capturing declines of 18.5%–18.9% and 2.1%–2.6% respectively, indicating some historical timing accuracy at this ticker. The cross-ticker track record shows a 45.00% well-timed rate across 20 prior sells, modestly above random, and while the company's fundamentals remain solid (P/E 44.89, +7.8% annual revenue growth, $83.7M net income), the substantial distance from the 52-week high combined with recent downward momentum provides context for the sale.

DOCU exec Chatwani sells 15,501 shares for $1,063,492.50 across 3 transactions; prior 2 DOCU sells poorly timed (+9.4% 90d gains missed)

Chatwani executed 3 separate sales totaling 15,501 shares for $1,063,492.50 between December 15–17, 2025, reducing his DOCU holdings by 18.1% from 85,698 to 70,197 shares. His prior trading pattern at DOCU shows mixed outcomes: his two most recent sales (2025-09-17) were well-timed with 90d declines of -18.5% and -18.9%, but his three earlier sales (2025-06-18) proved poorly timed, each missing subsequent 90d gains of +8.2%, +9.4%, and +9.4%. At his cross-ticker level, his 90d well-timed rate is 42.86% across 14 prior sells, suggesting only modest predictive accuracy. Current price of $67.79 is -31.0% from the 52-week high of $98.17, placing the stock in a depressed zone relative to recent peaks, though it has recovered +4.8% over the last 30 days.

Chief Legal Officer James P Shaughnessy sold 7,500 DOCU shares for $533,953.30 at $71.19 blended average as stock falls -8.1% in 30 days.

Shaughnessy executed 2 separate sales totaling 7,500 shares (7.5K shares) for $533,953.30 ($534.0K) on 2025-10-01, reducing his holdings from 62,942 to 55,442 shares (-11.9%). The CLO sold at a blended average price of $71.19, but the current price is now $68.10 (-36.4% from the 52-week high of $106.99) and down -8.1% over the 30 days since the sale. His prior 5 trades at DOCU show mixed timing: 3 of those 5 sales were well-timed at the 90-day mark, while his cross-ticker track record shows a 63.64% well-timed rate on 11 prior sells with positive average 90-day returns. The stock carries a high valuation (P/E 48.64) against modest revenue growth of +7.8% annually and has declined -13.8% over the past 90 days. This sell occurs amid broader weakness in the name and follows recent sales at better prices in July 2025.

DOCU CEO Thygesen sells 40,000 shares for $2.8M at $69.69 blended average; stock down -36.4% from 52-week high, -8.1% in 30 days

Allan C. Thygesen, President and CEO of DocuSign, sold 40,000 shares (22.7% of his pre-transaction holdings) across 4 separate sales totaling $2,787,428.28 on October 1, 2025, at prices ranging from $69.03 to $71.65. This sale occurred as DocuSign's stock has deteriorated substantially: it trades at $68.10, down 36.4% from its 52-week high of $106.99 and down 8.1% over the prior 30 days. Among Thygesen's 5 prior trades at DocuSign, 3 of the 5 prior sells exhibited well-timed outcomes at the 90-day mark, suggesting a demonstrated pattern of selling before or near declines at this specific ticker. With DocuSign trading at a 48.64 P/E against slowing growth of 7.8% annual revenue expansion and net income of $63.0M on $800.6M quarterly revenue, the timing of this large concentrated sale during an extended drawdown warrants attention to whether it reflects broader concerns about near-term momentum or execution.

Director Solvik Peter sold 15,000 DOCU shares at $81.48; retains 135,253 shares post-sale.

Solvik Peter, a Director, sold 15,000 shares (15.0K shares) of DOCUSIGN, INC. at $81.48 on 2025-09-15, representing a 10.0% reduction in his pre-transaction holding. The sale occurred while the current market price stands at $84.52, suggesting the director's execution price was below recent levels. The broader context shows DOCU trading -21.0% from its 52-week high of $106.99, though it has recovered +17.9% over the past 30 days and +12.3% over 90 days. With a P/E of 60.37 and recent quarterly revenue of $800.6M alongside net income of $63.0M, the company demonstrates solid fundamentals with annual revenue growth of +7.8%. The transaction itself represents a moderate, non-majority position liquidation by a board member, leaving substantial shareholding of 135,253 shares post-sale.