Workday founder's trust sold $37 million of stock the week it touted $600 million of AI revenue

David Duffield, who co-founded Workday▲+4.34% — Workday, up 4.34 percent today, the human-resources and finance software company, and still owns more than 10% of it, sold stock again on October 9, 2026↗, through his revocable trust ¹. The trust converted 99,835 Class B shares, the founder class that carries extra votes, into Class A and sold every one in six tranches at $185.70 to $191.70, about $18.7 million ¹. The one-for-one conversion turned control stock into sellable stock ¹.

Three days earlier, on October 6, the trust had done the same with 99,228 shares↗, about $18.6 million, a sale this publication examined on October 8 ². EDGAR logged ten Workday insider forms↗ between October 5 and 14, seven of them filed on a single day ³. Wire copy ran the latest sale as $18.4 million and called Duffield a director; his Form 4 leaves the director and officer boxes unchecked and marks him a 10% owner ¹⁴.

Eighteen reference customers get the product free for a year

At its Analyst Day on October 14↗, Workday put its AI portfolio near $600 million of annual recurring revenue, more than triple a year earlier, with AI set to carry about 70% of next year's selling motion ⁵. The same disclosure lists 18 companies in the Sana Enterprise Lighthouse program, Sana being the AI line Workday says is approaching $100 million of revenue on its own; they co-innovate and act as references in exchange for one year of waived licensing ⁵.

For that year, the customers fronting the AI story are not paying to be in it. Days earlier, at its Rising conference in Las Vegas, Workday marketed tools that break jobs into tasks to show leaders where AI should take over ⁶. No filing breaks out agent revenue, so nothing on the record shows how much of the $600 million rides on waived or discounted fees ⁷.

The reported numbers trail the story

In the August quarter, chief executive Aneel Bhusri said AI products drove more than 25% of new annual contract value↗ ⁷⁸. Total subscription backlog grew only 8.0%, after 10.9% and 12.2% in the two prior quarters, and free cash flow fell to $460 million from $588 million ⁷⁸. Revenue growth has slid from 18.2% to 12.8% in ten quarters ⁹.

Workday repurchased $1.3 billion of stock in that quarter, finished a $5 billion buyback sooner than expected and kept $4 billion of authorization open ⁷⁵. The issuer was buying its own shares in the same week its founder's trust sold his.

The selling plan predates the pitch by ten months

The sales ran on a Rule 10b5-1 plan, a pre-scheduled selling program the trust adopted on December 2, 2025, ten months before the Analyst Day ¹. The week's $37 million is about half a percent of the trust's remaining stake, some 35.6 million shares worth roughly $6.7 billion at those prices ¹².

Paid adoption is real: nearly 900 customers bought at least one agent in the trailing year, a subset showing roughly 12% uplift, and 25% of the core customer base now uses an AI product, against just over 10% a year earlier ⁵. The quarter closes October 31 ⁷. The report that follows shows whether backlog stabilizes, whether agent revenue is ever disclosed, and whether the free lighthouse year turns into invoices ⁷.