Workday CTO Leaves for Anthropic as AI Tools Pressure Enterprise Software

Workday faces mounting pressure as artificial intelligence reshapes the enterprise software space, and it’s starting to show at the top of its ranks. The company’s chief technology officer departed to join Anthropic as a member of technical staff, according to The Information.

The “member of technical staff” title is common at frontier labs such as Anthropic and OpenAI, as well as at large tech companies. It is used for technical roles across research and engineering, reflecting flatter structures and broader scope. While it is not an executive position, it is typically associated with senior technical work and product development.

Peter Bailis joined Workday in May 2025 and left last month. A Workday spokesperson confirmed his departure, and his new role is reflected on his LinkedIn profile.

At Anthropic, Bailis works on reinforcement learning systems that aim to make AI models run faster and with fewer errors. These systems are used to improve how models perform in live settings. The work focuses on reliability and speed in production use.

Workday named Gabe Monroy as chief technology officer after Bailis left. Monroy joined the company from Google Cloud in 2025.

Anthropic has posted roles tied to building software for hiring and employee management. The roles refer to “people products” that support hiring, training and promotions. These tasks are handled by HR software such as Workday.

Anthropic has used Workday software in the past. The company was a customer as recently as February. It has also sought candidates with experience in Workday, Salesforce and NetSuite.

AI firms are building software that handles tasks inside business workflows. Hiring and employee management involve repeat steps and structured data. These tasks can be handled by AI systems. Tools can draft job posts, screen candidates, and track employee data.

Enterprise software companies sell tools for these tasks today. AI firms are now building tools that can do some of the same work. This shift places pressure on vendors whose products depend on workflow management.

Anthropic has not announced a public HR product. The company is hiring engineers to build these systems. The work is focused on internal tools and future products.

The change in role for Bailis took place in March, according to his LinkedIn profile.

For all PYMNTS AI coverage, subscribe to the daily AI Newsletter.