GRAYSON BLAKE JEFFREY

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 CFO Grayson Blake Jeffrey sells 9,509 shares in 2 transactions for $790,234.93; remains with 112,160 shares post-sale.

Grayson Blake Jeffrey, Chief Financial Officer of DocuSign, executed 2 separate sales on 2025-09-17, disposing of a combined 9,509 shares (9.5K shares) for $790,234.93 at a blended average price of $83.10. His post-transaction holdings stand at 112,160 shares (112.2K shares), representing a -7.8% reduction from his prior 121,669-share position. Across his same-ticker history at DOCU, his 5 prior trades show mixed outcomes: only 1 of 3 completed 90-day measurable periods yielded negative returns (well-timed for a seller), with the most recent two July 2025 sales showing -2.1% and -2.6% at the 30-day mark. The current stock price of $84.52 sits -21.0% from its 52-week high of $106.99 and has risen +17.9% over the prior 30 days, suggesting the insider is selling into recent upside momentum rather than at a peak valuation.

DocuSign CFO Grayson Blake Jeffrey sells 11.2K shares for $867.0K as stock slides 27.9% from 52-week high

GRAYSON BLAKE JEFFREY executed 2 separate sales on 2025-07-01, totaling 11,214 shares for $867,014.40 at blended average price of $77.32. The sales occur as DocuSign (DOCU) has declined 27.9% from its 52-week high and dropped 13.5% over the prior 30 days, though the stock has been essentially flat (-0.3%) over 90 days. His remaining holdings of 99,509 shares represent a 10.1% reduction from his pre-transaction position of 110,723 shares. While his cross-ticker track record shows a 46.15% well-timed rate on prior sells with average 90-day returns of +8.0%, his prior sales at DocuSign present a mixed picture: 4 recent sales in March, April, and June show 30-day returns ranging from +18.6% to +19.2%, but his one measurable 90-day outcome (March 19 sale) returned -10.7%. The current filing offers limited forward-looking signal without FLAG disclosure or a clear pattern distinction from recent routine sales activity.

CFO Grayson Blake Jeffrey sold 15,143 shares at $74.80 avg; stock down 17.6% in 30 days, -29.7% from 52-week high.

Grayson Blake Jeffrey, CFO of DocuSign, executed 2 separate sales totaling 15,143 shares for $1,132,633.35, reducing his holdings by 12.0% to 110.7K shares. The sales occurred at a blended average price of $74.80, whereas the stock has since declined 17.6% over 30 days and trades at $75.25—29.7% below its 52-week high of $106.99. His prior 5 trades at DocuSign show a 3 of 3 well-timed 90-day outcome record (negative 90d returns after sells), indicating a pattern of selling ahead of declines at this specific ticker. However, across his broader cross-ticker open-market history, his 90d well-timed rate stands at 46.15% with an average 90d return of +8.0% following sells, suggesting his timing precision varies significantly by ticker.

DocuSign CFO sells 8,000 shares (8.0K) for $608,712.46; stock down 28.6% from 52-week high

Grayson Blake Jeffrey, Chief Financial Officer of DocuSign, executed two separate sales totaling 8,000 shares for $608,712.46 on 2025-04-15 at blended average price $76.09, reducing his holdings from 94,156 to 86,156 shares. The sales occur as DocuSign's stock trades 28.6% below its 52-week high of $106.99 and has declined 8.4% over 30 days and 16.2% over 90 days—a period of material price weakness. Across his cross-ticker open-market history, Jeffrey has executed 13 prior sells with a 90-day well-timed rate of 37.50%; however, at DocuSign specifically, his 5 prior trades show measurable outcomes mixed at best (30-day returns of -1.2% and -2.3% on the two most recent trades), with 0 of 0 prior sells at this ticker demonstrating positive 90-day outcomes. The current sale occurs during a notably depressed valuation window relative to recent highs, while fundamentals remain stable (P/E of 7.72, annual revenue growth of 7.8%, net income of $62.4M on revenue of $754.8M in the latest quarter).

CFO Grayson Blake Jeffrey sells 16,111 shares of DOCU for $1,340,474.46; prior DOCU sales 100% well-timed.

Grayson Blake Jeffrey, CFO of DocuSign, executed 3 separate sales totaling 16,111 shares for $1,340,474.46 on 2025-03-19 at a blended average price of $83.20, reducing his holdings by 14.6% to 93,960 shares. His prior 5 trades at DOCU show a perfect pattern: 3 of 3 prior sells at this ticker achieved negative 90-day returns (-8.4%, -13.1%, -3.3%, -9.2%, -4.3%), meaning he sold before subsequent declines. The current price of $85.11 is -20.4% from the 52-week high and -9.8% over the past 90 days, consistent with the downtrend environment where his prior DOCU sells proved well-timed. With fundamentals stable (P/E 8.60, +7.8% annual revenue growth, $62.4M net income on $754.8M revenue), the repeated pattern of selling into weakness before further declines warrants attention.

CFO Grayson Blake Jeffrey sells 8,000 DOCU shares for $695,209.92; holds 77,851 post-sale.

GRAYSON BLAKE JEFFREY, Chief Financial Officer, executed 2 separate sales totaling 8,000 shares for $695,209.92 on 2025-02-14, reducing holdings from 85,851 to 77,851 shares (-9.3%). The blended average price of $86.90 is 0.5% below the current price of $87.34 and 18.4% below the 52-week high of $106.99. His prior sales at DOCU show a pattern of negative near-term outcomes: the two most recent December 2024 sales fell 8.4% and 3.3% to 4.3% over 30 days, while earlier October 2024 sales gained 16.8% over 30 days. Against his cross-ticker track record of 8 prior sells with a 0.00% well-timed rate at the 90-day mark, this sale occurs as the stock sits -2.5% over 30 days and +10.8% over 90 days, suggesting recent momentum in the name. The company shows solid fundamentals with $754.8M in latest quarterly revenue, +9.8% annual growth, and a P/E of 17.43, offering limited fundamental concerns to justify the sale timing.

CFO Grayson Blake Jeffrey sells 15,588 shares of DOCU at $97.78; holds 85,851 shares post-transaction.

Grayson Blake Jeffrey, Chief Financial Officer, sold 15,588 shares at $97.78 on 2024-12-18, reducing his holdings from 101,439 to 85,851 shares (a 15.4% reduction). The sale occurred near DocuSign's 52-week high of $106.99, with the stock currently trading 13.4% below that peak. Jeffrey's cross-ticker track record shows 7 prior open-market sells with a well-timed rate of 0.00%, indicating that none of his previous sales preceded declines—a pattern of systematically selling into strength rather than before downturns. At the same ticker (DOCU), his prior measurable sale from 2024-09-18 posted a 90-day return of +77.0%, suggesting he sold well before significant appreciation. The CFO's recent activity—two additional sales on 2024-12-16 immediately preceding this transaction—suggests a deliberate liquidation sequence, though the outcome of the current sale remains unmeasured.

DocuSign CFO Grayson Blake Jeffrey sold 8,000 shares ($758.2K) in 2 separate sales at blended avg $94.77.

Grayson Blake Jeffrey, Chief Financial Officer of DocuSign, executed 2 separate sales totaling 8,000 shares for $758,196.35, reducing his holdings from 109,439 to 101,439 shares (a -7.3% reduction). The sales occurred at $94.42 and $95.41 per share, below the current price of $98.17 and well below the 52-week high of $106.99. His same-ticker history at DocuSign shows a mixed timing pattern: of the 3 prior measurable sales outcomes, zero achieved negative 90-day returns (0 of 3 well-timed). Most recently, his September 2024 sale at DocuSign yielded +77.0% after 90 days—a poorly-timed sale where the stock rallied significantly post-execution. The June 2024 sales similarly produced positive 90-day returns (+11.9%, +9.9%), continuing the pattern of selling before rallies rather than declines.

DOCU CFO sold 9,552 shares for $657,193.12; stock at 52-week high, +27.9% in 30 days, yet exec disposed position.

Grayson Blake Jeffrey, DOCU's Chief Financial Officer, executed 2 separate sales totaling 9,552 shares for $657,193.12 on 2024-10-15 at a blended average price of $68.80. This represents a -10.9% reduction in his post-transaction holdings to 78,265 shares. The timing is notable: the stock is currently at $72.60, exactly at its 52-week high (+0.0% from peak), having appreciated +27.9% over the past 30 days and +33.0% over 90 days. His prior sales at DOCU showed mixed timing outcomes (0 of 2 measured prior sells achieved negative 90-day returns), and his cross-ticker track record shows 0.00% well-timed rate on prior sales, suggesting a pattern of selling into strength rather than downturns. The concurrent strength in fundamentals—revenue of $736,027,000.00 in the latest quarter and net income of $888,211,000.00—provide no evidence of deteriorating business conditions that would justify immediate liquidation.