American billionaire David Duffield sells $18.6 million of Workday shares

American billionaire David Duffield, the co-founder of human resources software maker Workday Inc., has sold $18.6 million of the company's shares, according to a regulatory filing reported by Investing.com.

Duffield sold 99,228 Class A shares on Oct. 6 at prices ranging from $184.12 to $190.18 each, for a total of $18,587,115. The sale was made under a Rule 10b5-1 trading plan adopted by one of his trusts on Dec. 2, 2025. Such plans allow company insiders to schedule share sales in advance so they cannot be accused of trading on inside information.

On the same day he converted 99,228 of his Class B shares into Class A shares, the stock that trades publicly. Workday's Class B shares carry extra voting rights and can be converted into Class A shares at any time.

A $6.7 billion stake

The sale barely dents Duffield's holding. After the transactions he held 105,049 Class A shares and 35,580,586 Class B shares through a revocable living trust that he controls as trustee and sole beneficiary.

That stake of about 35.7 million shares was worth about $6.7 billion at Workday's recent price of $186.59, which gave the company a market value of about $45.3 billion. Duffield is also a director of the company and one of its largest shareholders.

Workday's shares have risen about 66% over the past six months. Analysts remain split on the stock. Jefferies cut its price target to $210 from $220 and kept a hold rating, citing slowing growth in revenue and backlog, while Needham rates it a buy with a $230 target. Cantor Fitzgerald has an overweight rating after the company cut about 2.5% of its workforce.

Two software empires

Duffield, 86, has built two of the biggest companies in business software. He founded PeopleSoft in 1987, building it into a leading maker of human resources and finance software. Oracle Corp. took control of the company in 2005 after an 18-month hostile takeover battle, paying about $10.3 billion.

Within months Duffield teamed up with Aneel Bhusri, a former PeopleSoft executive, to start Workday, which sells cloud-based software for managing payroll, staff and finances. Workday went public in 2012.

Duffield is also one of America's best-known animal welfare donors. He and his wife, Cheryl, created Maddie's Fund, named after their late miniature schnauzer, which has given hundreds of millions of dollars to help shelters find homes for dogs and cats.