ADSK Autodesk, Inc. Insider Trading

Director John T Cahill bought 2,000 ADSK shares at $189.20; stock down -42.6% from 52-week high of $329.09

John T Cahill (Director) purchased 2,000 shares at $189.20 on 2026-06-23, doubling his holdings from 2,000 to 4,000 shares. The purchase occurred as ADSK trades at $188.78, down -42.6% from its 52-week high of $329.09 and -21.7% over the past 30 days. In his prior ADSK purchase on 2025-03-21, the stock returned +10.5% over 90 days following that buy, representing well-timed execution. The current transaction is noteworthy because 2 other insiders also bought within the past 14 days, creating a cluster pattern of director-level purchases during a period of significant price weakness. With the company reporting $1.9B in quarterly revenue, +17.5% annual growth, and a P/E of 27.24, the cluster activity coincides with a material decline from prior valuation levels.

CEO Andrew Anagnost buys 2,460 shares of ADSK at $202.66 as stock trades -41.3% from 52-week high

Andrew Anagnost (President and CEO) purchased 2,460 shares (2.5K shares) of Autodesk at $202.66 on 2026-06-16, increasing his holdings from 200,503 shares to 202,963 shares (+1.2%). The transaction occurs in a materially weakened market context: the stock trades at $193.07, down -41.3% from its 52-week high and down -20.7% in the prior 30 days. Anagnost's cross-ticker track record shows 8 prior sales with a 90-day well-timed rate of 100.00%, and his prior 5 trades at ADSK (all sales from 2023-2024) were unanimously well-timed at the 90-day mark, with post-sale declines ranging from -1.2% to -7.3%. This buy enters against a backdrop of significant recent downward price momentum and an insider whose historical sales have consistently preceded further declines, yet the current purchase magnitude of +1.2% of existing holdings is modest relative to the company's scale (market cap $40.7B, latest quarterly revenue $1.9B, net income $491.0M).

CFO Janesh Moorjani buys 2,500 ADSK shares at $197.67; stock down -21.5% in 90 days from $329.09 high.

Janesh Moorjani, EVP and Chief Financial Officer, purchased 2,500 shares of Autodesk at $197.67 on 2026-06-15, increasing his holdings from 48.5K to 51.0K shares. The purchase occurred as ADSK trades -39.6% from its 52-week high of $329.09 and has declined -21.5% over the past 90 days. Moorjani's cross-ticker track record shows 4 prior sells with a 90-day well-timed rate of 100.00%, indicating his prior sales have consistently been followed by further stock declines; however, this transaction is a purchase rather than a sale, and his prior track record timing does not directly predict the outcome of a buy decision. The company fundamentals remain solid, with annual revenue growth of +17.5%, net income of $491.0M, and a market cap of $41.9B, though the stock's recent weakness suggests either near-term headwinds or potential valuation adjustment.

Director Stacy J Smith buys 3,435 shares at avg $231.17; stock now -29.7% from 52-week high.

Stacy J Smith, a director at Autodesk, executed 2 separate purchases totaling 3,435 shares for $794,054.34 on 2026-05-29, increasing her holdings by 14.9% to 26,517 shares. The timing of this acquisition is notable: at $231.17 blended average, she bought within 1.9% of the current price ($231.31), yet the stock has declined 5.9% over the past 90 days and sits 29.7% below its 52-week high of $329.09. Across her cross-ticker track record, Smith's prior 2 buys averaged a 90-day return of 4.5% with a 100% win rate; however, at ADSK specifically, her 5 prior trades from late 2023 to early 2024 were all sells, with no measurable 90-day outcomes available. The company's fundamentals remain solid—revenue growth of 17.5% annually and a net income of $491.0M on $1.9B quarterly revenue—though the P/E of 33.38 suggests elevated valuation relative to recent equity performance.

Autodesk EVP Steven Blum executes 4 scheduled sales totaling 22,420 shares for $7,258,475.52 via 10b5-1 plan

Steven Blum, Chief Operating Officer at Autodesk, executed 4 separate sales totaling 22,420 shares at prices ranging from $322.51 to $325.03 on 2025-09-05, reducing his holdings from 35,519 shares to 13,099 shares. This transaction is part of a pre-arranged 10b5-1 trading plan, meaning the sales were scheduled in advance and not driven by discretionary decision-making at the time of execution. The 63.1% reduction in his pre-transaction holdings represents a material portfolio shift, though the scheduled nature of the plan precludes timing-based inference about Blum's current views on Autodesk's valuation or near-term prospects.

EVP Ruth Ann Keene sold 2,761 shares of Autodesk at $315.10; holds 80,255 shares post-sale.

Keene Ruth Ann, Executive Vice President of Corporate Affairs and Chief Legal Officer, sold 2,761 shares of Autodesk on 2025-09-03 for $315.10 per share, reducing her holdings by 3.3% to 80,255 shares. The transaction occurred near the 52-week high of $321.27, with the stock currently trading at $319.93. The sale represents a modest reduction in a substantial position and lacks sufficient context from this filing alone—without knowledge of whether this trade was scheduled under a 10b5-1 plan or discretionary—to characterize its strategic timing or significance. Autodesk maintains strong fundamentals with $1.8B in quarterly revenue, net income of $313.0M, and annual revenue growth of 11.5%, though the elevated P/E of 65.29 reflects current market expectations. The transaction magnitude and position retention do not suggest material conviction shifts in either direction.

Director Howard Ayanna sold 3,159 shares of ADSK at $325.00 for $1,026,675; holdings reduced 41.8% to 4,393 shares.

Howard Ayanna, a Director of Autodesk, sold 3,159 shares at $325.00 on 2025-08-29, reducing his position from 7,552 shares to 4,393 shares—a 41.8% reduction in holdings. The transaction occurred at $325.00, a price 3.3% above the current trading price of $314.70 and near the 52-week high range of $238.84–$321.27. The sale is notable for its scale relative to remaining holdings, effectively halving the director's position. Without information about a trading plan or prior trading patterns, the transaction appears as a discretionary reduction in a company trading at a P/E of 66.53 with solid fundamentals (11.5% annual revenue growth, $152.0M net income), but this metric alone does not clarify the motivation.

EVP Rebecca Pearce sells 6,129 shares at $323.06 avg for $1,980,040; 31.5% portfolio reduction

Rebecca Pearce, EVP Chief People Officer at Autodesk, executed 2 separate sales on 2025-08-29, selling 2,377 shares at $320.00 and 3,752 shares at $325.00, totaling 6,129 shares for $1,980,040.00 and reducing her holdings by 31.5% from 19,440 to 13,311 shares. The blended average transaction price of $323.06 sits just below the 52-week high of $321.27, and the stock is currently trading at $314.70, down 2.0% from that peak. Pearce's same-ticker sale history at ADSK shows 5 prior trades with a 0 of 2 well-timed rate on the 90-day mark (her prior two measurable 90-day outcomes were +9.9% and +7.8%, indicating the stock rose after her prior sales), suggesting her timing on this ticker has not historically preceded declines. The transaction itself represents a material reduction in her position and warrants monitoring given her senior role in human capital strategy at a $67.3B market-cap company trading at a P/E of 66.53.

EVP Chief People Officer Pearce Rebecca sold 3,251 shares of ADSK at $315.00 on 2025-07-03; post-sale holdings 19,440 shares.

Pearce Rebecca, Chief People Officer, sold 3,251 shares (-14.3% vs pre-transaction holdings) for $1,024,065.00 as ADSK traded near its 52-week highs at $315.00, only -1.4% below the $321.27 peak. Her cross-ticker track record shows prior sells averaging +2.0% 30-day return and +8.9% 90-day return with a 0.00% well-timed rate—meaning those sales were followed by stock appreciation, not declines. At this same ticker (ADSK), her prior measurable sales in December 2023 also preceded gains (+3.0% and +1.0% at 30 days, +9.9% and +7.8% at 90 days), establishing a pattern of poorly-timed exits from a rising position. The sale occurs in a company with strong fundamentals (revenue $1,633,000,000.00, net income $152,000,000.00, +11.5% annual growth) and elevated valuation (P/E 66.95), yet the insider's historical behavior at this specific ticker suggests she has not successfully timed downturns. The most recent timing data point for this filing cannot be measured yet, leaving the current transaction outcome unknown.

EVP Rebecca Pearce sold 3,110 ADSK shares at $310.00 (total $964,100), reducing holdings by 12.1%; stock up 17% in 90 days.

Rebecca Pearce, Chief People Officer, sold 3,110 shares at $310.00 on 2025-06-30, reducing her holdings from 25,801 to 22,691 shares. The sale occurred just six days after another sale at ADSK on 2025-06-24, suggesting a deliberate liquidation pattern rather than an isolated transaction. Against the broader market context, ADSK stock has appreciated 17.0% over 90 days and remains near its 52-week high (3.6% below peak at $321.27), and the company shows solid growth with 11.5% annual revenue growth and a market cap of $66.2B. Across her same-ticker history at ADSK, Pearce's two prior measurable sales in December 2023 both saw positive 90-day returns (post-sale appreciation), indicating historically poor timing; her current cross-ticker track record shows a 0.00% well-timed sell rate, suggesting her sales have not generally preceded stock declines. The restricted narrative here is simply that a senior executive has exited a portion of a strong-performing position in a period of rapid appreciation.