Workday Hands Out Free AI While Duffield's Trust Sells $18.8M at a Time

The charge: AI that is signed but unused

Workday's AI problem is not rejection. It is shelfware. Field reporting out this week↗, drawn from five consultants who serve more than 2,000 Workday customers, finds them pulling Workday data into agents from Anthropic and Microsoft, or building their own with firms like NinjaOne and Druva, rather than using the AI built into the HR and finance suite ¹². At one consultancy with more than 400 Workday customers, about half have signed usage-based AI agreements, only 10 to 20 percent actively use Workday's AI, and none use Sana Enterprise, the agent product released in March↗ ²³. Workday's response is to pay for attention: free credits, a free year of Sana Enterprise for some large accounts, and API overage charges waived from May 2026 through February 2027 ².

The company's exhibit: 5,500 agents, no price tag

Workday's counter-numbers are real and carefully chosen. Customers using at least one Workday agent grew more than 35 percent sequentially to about 5,500 of roughly 11,500, a company-claimed count that does not say how many pay ²⁴. AI drove more than a quarter of new contract value last quarter↗, and Workday puts agents plus Sana on pace for $600M a year ⁴². Aneel Bhusri, back as chief executive since February, told analysts in August he had not met a single customer looking to replace Workday ³⁷.

The receipts: growth stuck near 13 percent

The core business tells what the usage counts avoid. Revenue rose 12.8 percent to $2.649B in the July quarter↗, and analysts expect 9.7 percent for the quarter ending January 2027 ⁵². Workday cut about 500 jobs on September 29, its second layoff round of 2026, without citing AI as a cause ⁷; six days later it shipped a global workforce report arguing AI rewrites jobs more than it cuts them ⁸, the pairing The Inference covered on October 7. It declined to comment on an August report that Silver Lake had weighed taking the roughly $45B company private ².

The whale: a 10 percent holder selling weekly

David Duffield co-founded Workday, and his trust is a 10 percent stockholder ⁸. On October 6 it proposed selling 99,228 shares worth $18.75M↗, after nine 10b5-1 sales since July 9 that grossed $163.4M, about $185 a share on average ⁸. EDGAR shows at least twenty such notices↗ from the trust this year, from April 9 onward, under a plan adopted in December 2025 ⁹⁸. Pre-scheduled sales prove nothing about motive; the calendar still puts the founder's trust in a near-weekly sell rhythm while the company discounts its own AI.

The verdict watch

February 2027 is the tell: the API waiver ends and the free years expire, so conversion to paid, or the lack of it, lands in the subscription line. The $600M pace still has no paying-customer count behind it ². The risk is not that agents replace Workday. It is that Workday becomes the plumbing someone else bills for.