The CTO of Workday exchanged his executive position for a technical staff role at Anthropic.

      In summary: Peter Bailis, who took on the role of chief technology officer at Workday in May 2025, departed from the company last month and has accepted a position as a member of the technical staff at Anthropic, focusing on reinforcement learning engineering. This transition trades a C-suite title for a closer technical engagement at the forefront of AI, placing Bailis in a company that is actively developing the type of HR software Workday offers.

      An Anthropic spokesperson confirmed the hire, which was also reported by Business Insider. Bailis’s profile has been removed from Workday’s leadership pages, and his LinkedIn reflects this change. Before his time at Workday, Bailis was vice president of engineering at Google Cloud, overseeing AI initiatives for data such as Conversational Analytics, NL2SQL, and retrieval-augmented generation for structured data. Earlier, he founded Sisu Data, a decision intelligence firm, and was an assistant professor of computer science at Stanford University, where he co-led the DAWN project focused on data-intensive applications. His expertise in data systems and recent AI work at Google Cloud makes him an atypical choice for a reinforcement learning role, indicating Anthropic's interest in engineering that links model training with practical product development.

      From executive to individual contributor

      The position Bailis has taken at Anthropic, member of technical staff (MTS), is the standard engineering title at both Anthropic and OpenAI, applied uniformly across research and engineering regardless of seniority. OpenAI president Greg Brockman has publicly discussed this structure, explaining that the labs aim not to categorize people as researchers and engineers but to view the MTS title as a signal of a flat technical hierarchy rather than a demotion. In practice, the title encompasses a broad spectrum of experience and pay: base salaries for MTS at Anthropic range from approximately $300,000 to $405,000, while at OpenAI, the range spans from about $210,000 to $530,000, with equity grants elevating total compensation well into the seven figures for senior roles.

      For Bailis, the trade-off is clear. The CTO position at a company like Workday, which has around $8 billion in annual revenue and 18,000 employees, carries a level of institutional authority that an individual contributor role at an advanced AI lab does not. However, it offers a direct connection to the models being developed, training decisions being made, and the research agenda being set, without the layers of organizational management that separate a CTO from hands-on work. Anthropic, with a reported revenue run rate exceeding $30 billion and over 1,000 enterprise clients, each spending more than $1 million annually, is no longer just a research facility generating revenue — for a technically driven executive, the scale of the engineering challenges it now faces is a significant attraction.

      Why Bailis is valuable to Anthropic now

      An Anthropic spokesperson confirmed that Bailis will focus on reinforcement learning engineering. This area covers a wide scope at a company where reinforcement learning from human feedback is crucial for model alignment, and RL-based training techniques are being utilized for agent behavior and tool usage. Beyond general engineering capabilities, what Bailis brings is a thorough understanding of the enterprise software stack that Anthropic is now entering as a product developer, rather than just an API provider.

      Specifically, The Information reported that Bailis’s onboarding aligns with Anthropic’s initiative to develop HR applications. Anthropic has already introduced Claude plugins tailored for HR purposes, such as creating job descriptions, onboarding materials, and offer letters. He spent recent years immersed in the enterprise HR and finance software sector, first with Google Cloud, where he developed AI products integrated with structured enterprise data, and later as Workday’s CTO, where he spearheaded the company's agentic AI strategy. This domain expertise is now being directed towards Anthropic’s enterprise product roadmap from within.

      The competitive irony is significant. Workday’s CEO, Carl Eschenbach, publicly stated in February 2026 that Anthropic, Google, and OpenAI all use Workday’s software internally. The company that licensed software from Workday has now hired its former CTO to create products that compete for the same enterprise HR budgets.

      Anthropic’s enterprise ambitions

      Bailis’s hiring makes more sense considering how aggressively Anthropic has been establishing enterprise distribution infrastructure in recent months. In early March, Anthropic launched a marketplace for Claude-powered enterprise software, letting companies with committed API spending purchase third-party applications built on Claude, with Anthropic waiving the typical revenue share charged by cloud providers. Initial partners included Snowflake, legal AI firm Harvey, and developer platform Replit.

      Shortly after, Anthropic committed $100 million to a new Claude Partner Network with anchor partners like Accenture, Deloitte, Cognizant, and Infosys, formalizing collaborations to expedite Claude implementations within the largest enterprises. The company indicated plans to increase that commitment in the future and was planning to grow its partner-facing