Will Autodesk CEO Andrew Anagnost establish a 10b5-1 selling plan by December 2026?

The base rate for long-tenured tech CEOs establishing 10b5-1 plans in a given 12-month window is moderate, but Anagnost has been CEO for ~9 years without one. Post-investigation clearance (Aug 2025) removed the primary legal obstacle, yet 6 months passed with zero discretionary selling. Multiple other C-suite officers have active 10b5-1 plans, so the CEO's absence is a deliberate choice. The 10-month remaining resolution window adds some probability, and the $66M concentrated position creates rational diversification pressure. However, revealed preference over 9 years of not establishing a plan is a strong prior. The charitable gift of 26,268 shares shows comfort with non-market dispositions but not selling.

The strongest fact is that Anagnost has been CEO for 9 years and has never established a 10b5-1 plan. The longer someone hasn't done something, the less likely they are to start in any given period. The post-investigation clearance has been available since Aug 2025 — 6 months passed without action, suggesting he is not motivated to sell. The Starboard settlement and board refresh could create strategic uncertainty, but the 2-month data gap (Jan-Feb 2026) is unlikely to contain a surprise filing given the strong behavioral pattern. The Black Swan Beacon's 5-10% CEO departure probability adds marginal 10b5-1 plan probability.

Consider the counterfactual: what would need to change for Anagnost to establish a 10b5-1 plan? Portfolio diversification need exists at $66M single-stock concentration. Pre-retirement planning — 9 years approaches typical CEO tenure at major software companies. Board pressure from Starboard-influenced directors could shift governance dynamics. The 78,749 unvested RSUs will vest over time, increasing liquid position and potentially triggering diversification planning. However, the 6-month data gap and the strong 'no selling' signal from Jun-Dec 2025 dominates. The 2-month staleness window (Jan-Feb 2026) could contain an unreported filing, but this is low probability given the behavioral pattern.

Zero discretionary selling in a 6-month window post-investigation clearance is the most telling fact. If you cleared a major legal overhang and still didn't sell or establish a plan, you're not planning to. The 10-year tenure argument cuts both ways — he's been there 9 years without a plan, establishing a strong behavioral baseline. Many founder/long-tenure CEOs never establish 10b5-1 plans. The ~$66M position is concentrated but not unusual for a $60B+ company CEO. The 10-month remaining window adds some probability but doesn't overcome the strong prior of 9 years of revealed preference against selling.

The resolution window extends through end of 2026 — a full additional 10 months. Potential triggers for plan establishment: succession planning, new compensation structure, tax planning around RSU vesting schedules, estate planning. The 78,749 unvested RSUs will vest over time, increasing liquid equity and creating tax optimization opportunities that 10b5-1 plans facilitate. However, the revealed preference is clear — he's had 9 years to do this and hasn't. The 2-month data gap (Jan-Feb 2026) could contain a filing, but this would be inconsistent with the strong prior. The COO, CLO, CPO, and a director all have active plans, meaning the CEO's absence is a deliberate choice.

The fact that COO, CLO, CPO, and a director all have active 10b5-1 plans while the CEO does not is highly informative. It demonstrates the company's insider trading compliance program actively supports these plans, so the CEO's absence is a revealed preference, not an institutional barrier. The post-investigation window was the most natural establishment point and it passed without action. The Insider Investigator's ALIGNED assessment vs Fugazi Filter's MIXED assessment is directly tested by this market — the behavioral evidence strongly supports the ALIGNED reading. The 10-month window adds marginal probability but the prior is strong.

9 years as CEO with zero history of 10b5-1 plan and zero discretionary selling even after investigation cleared. Strongest factor is revealed preference over long tenure. The 10-month remaining window and RSU vesting add some probability. Other insiders have plans, confirming CEO's absence is a choice.

Post-clearance inaction is the dominant signal. Other insiders have active plans; CEO deliberately doesn't. Long remaining window adds some probability but the base rate of 'never done it in 9 years' is the strongest evidence. The charitable gift route suggests comfort with non-sale dispositions. GOVERNANCE_ALIGNMENT = ALIGNED from Insider Investigator is well-supported by behavioral data.

CEO departure probability 5-10% per Black Swan Beacon — if departure happens, 10b5-1 plan likely precedes it. Add probability of diversification without departure due to RSU vesting and concentration. But 9-year track record of no plan is dominant signal. The 10-month resolution window is the main upside driver against a strong prior.