SeekOut’s Anoop Gupta has stepped down as CEO, taking over the company’s AI hiring from tech expert Sean Thompson.

Anoop Gupta is stepping down as CEO of SeekOut, the Bellevue-based recruiting agency he founded in 2017, handing the reins to software veteran Sean Thompson and focusing on growing heirloom tomatoes, among other things.

Gupta, 67, whose long career at Microsoft included stints as Bill Gates’ technology assistant and head of Skype and Exchange, plans to step down full time on May 4 and become executive chairman. This decision has been taken for several years, he said in an interview.

“I’m a smart person and an entrepreneur, but to me, the most important things are people and communication and storytelling and, you know, vegetables,” he said.

As the new CEO, Thompson said he plans to focus on expanding SeekOut Spot — the AI ​​recruiting service launched last year — while pursuing recruitment agency acquisitions to help fuel long-term growth.

A veteran of business and technology in the Seattle area, Thompson most recently led NAVEX, a privately held governance and compliance software company, as president and CEO from 2022 through early 2025. He previously held senior roles at SAP and Microsoft, and founded AI startup Nuiku, which he sold to Nortek in 2016.

Thompson lives in Bellevue, about two miles from SeekOut’s office, and has spent the past year in retirement, riding horses on his Montana property and taking on advisory roles.

Now he’s back on the starting scale. In an interview, Thompson said that SeekOut’s opportunity to leverage advances in agent AI was too compelling to pass up.

“There’s a huge market out there, and we can fundamentally change the way people approach the search process, and the way hiring managers approach the search process,” Thompson said. “Being able to make an impact is what really inspired me.”

Announcing the news Thursday morning, the company said SeekOut founder Aravind Bala, who has led product and engineering since the company’s inception, will continue as chief technology officer and work closely with Thompson on the next phase of growth.

Gupta and Bala worked together at Microsoft on Office Mix, an online presentation service, before leaving to start a company together. As GeekWire reported at the time, they initially pursued a messaging service based on the idea that recipients — not senders or platforms — should be compensated for their attention. That idea didn’t take off, but the tool they built to find their potential customers became the foundation of SeekOut.

SeekOut has raised a total of $189 million from investors including Tiger Global, Madrona Venture Group, and Mayfield, hitting a $1.2 billion Series C valuation in early 2022. It grew rapidly and increased the number of employees, but it reduced the workforce twice – in October 2023 and May 2024 – as the economy changed and the hiring contract.

Today it has about 150 employees, more than 750 corporate clients, and a bank balance of more than $100 million, according to the Guptas. That gives SeekOut leverage to deepen its AI efforts and time to pursue the acquisitions Thompson described as central to its plans.

SeekOut conducted a formal legal search for more than six months, but Thompson was unsuccessful in that process. He was first brought on as an acquisition strategy advisor to SeekOut, through a partnership that included SeekOut general counsel Sam Shaddox — his outside counsel during the Nuiku sale — and the Seattle M&A advisory firm Alexander Hutton, where his brother James Thompson worked.

Through that advisory role, Thompson connected with Bala, and the CEO conversation took off from there. “It clicked, it went fast,” Gupta said.

SeekOut operates in two areas: Recruit, an AI-powered platform that employers can use to search over a billion candidate profiles; and Spot, a service that combines AI agents with SeekOut recruiters to deliver interview-ready candidates to hiring managers in about two weeks. Under Thompson, Spot is expected to become more focused.

As executive chairman, the Guptas estimate he will spend 20% to 25% of his time in the role. More broadly, he said, he’s worried about the societal impact of AI, and wants to make more time for things that technology can’t accelerate, like family, relationships, and community.

“Tomatoes don’t grow fast,” he said. “They still take a season to grow.”