Anoop Gupta is stepping down as CEO of SeekOut, the Bellevue-based recruiting startup he co-founded in 2017, handing the reins to enterprise software veteran Sean Thompson and turning his attention to growing heirloom tomatoes, among other pursuits.
Gupta, 67, whose long Microsoft career included stints as Bill Gates’ technical assistant and head of Skype and Exchange, plans to step down from his full-time role May 4 and become executive chairman. The decision has been a few years in the making, he said in an interview.
“I am a geek and an entrepreneur, but to me, the most important things are the people and the connections and the storytelling and, you know, vegetables,” he said.
As the new CEO, Thompson said he plans to focus on scaling SeekOut Spot — the agentic AI recruiting service launched a year ago — while pursuing acquisitions of recruiting agencies to help fuel long-term growth.
A Seattle-area business and technology veteran, Thompson most recently led NAVEX, a private-equity backed governance and compliance software company, as president and CEO from 2022 until early 2025. He previously held senior roles at SAP and Microsoft, and co-founded the AI startup Nuiku, which sold to Nortek in 2016.
Thompson lives in Bellevue, about two miles from SeekOut’s office, and spent the past year in semi-retirement, riding horses on his Montana property and taking on board advisory roles.
Now he’s getting back in the startup saddle. In an interview, Thompson said SeekOut’s opportunity to take advantage of progress in agentic AI was too compelling to sit out.
“There’s a large market out there, and we can fundamentally change the way candidates experience the search process, and the way hiring managers approach the search process,” Thompson said. “Being able to make an impact is really what inspired me.”
Announcing the news Thursday morning, the company said SeekOut co-founder Aravind Bala, who has led product and engineering since the company’s founding, 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 launch 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 a tool that they built to find 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 valuation with its Series C in early 2022. It grew rapidly and expanded headcount, but cut staff twice — in October 2023 and May 2024 — as the economy turned and the recruiting market contracted.
Today it has roughly 150 employees, more than 750 corporate customers, and over $100 million in the bank, according to Gupta. That gives SeekOut the runway to deepen its AI initiatives and time to pursue the acquisitions Thompson described as central to his plans.
SeekOut ran a formal executive search for more than six months, but Thompson didn’t come through that process. He was initially brought in as an advisor on SeekOut’s acquisition strategy, through connections including SeekOut general counsel Sam Shaddox — his outside counsel during the sale of Nuiku — and the Seattle M&A advisory firm Alexander Hutton, where his brother James Thompson works.
Through that advisory work, Thompson connected with Bala, and the CEO conversation evolved from there. “It clicked, and moved just very fast,” Gupta said.
SeekOut operates in two areas: Recruit, an AI-powered platform that recruiters can use to search more than a billion candidate profiles; and Spot, the service that pairs AI agents with SeekOut’s own recruiters to deliver interview-ready candidates to hiring managers in about two weeks. Under Thompson, Spot is expected to be the major focus.
As executive chairman, Gupta estimates he’ll spend 20% to 25% of his time on the role. More broadly, he said, he worries about the societal impact of AI, and wants to make more time for the things technology can’t accelerate, such as family, relationships, and community.
“Tomatoes don’t grow any faster,” he said. “They still take a season to grow.”
