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 program veteran Sean Thompson and turning his consideration to rising heirloom tomatoes, amongst different pursuits.
Gupta, 67, whose lengthy Microsoft profession included stints as Invoice Gates’ technical assistant and head of Skype and Change, plans to step down from his full-time function Could 4 and turn into govt chairman. The choice has been a number of years within the making, he mentioned in an interview.
“I’m a geek and an entrepreneur, however to me, an important issues are the folks and the connections and the storytelling and, you understand, greens,” he mentioned.
As the brand new CEO, Thompson mentioned he plans to concentrate on scaling SeekOut Spot — the agentic AI recruiting service launched a 12 months in the past — whereas pursuing acquisitions of recruiting businesses to assist gas long-term development.
A Seattle-area enterprise and expertise veteran, Thompson most just lately led NAVEX, a private-equity backed governance and compliance software program firm, as president and CEO from 2022 till early 2025. He beforehand held senior roles at SAP and Microsoft, and co-founded the AI startup Nuiku, which bought to Nortek in 2016.
Thompson lives in Bellevue, about two miles from SeekOut’s workplace, and spent the previous 12 months in semi-retirement, driving horses on his Montana property and taking over board advisory roles.
Now he’s getting again within the startup saddle. In an interview, Thompson mentioned SeekOut’s alternative to make the most of progress in agentic AI was too compelling to take a seat out.
“There’s a big market on the market, and we will essentially change the way in which candidates expertise the search course of, and the way in which hiring managers strategy the search course of,” Thompson mentioned. “Having the ability to make an influence is absolutely what impressed me.”
Asserting the information Thursday morning, the corporate mentioned SeekOut co-founder Aravind Bala, who has led product and engineering because the firm’s founding, will proceed as chief expertise officer and work carefully with Thompson on the following part of development.
Gupta and Bala labored collectively at Microsoft on Workplace Combine, a web-based presentation service, earlier than leaving to launch an organization collectively. As GeekWire reported on the time, they initially pursued a messaging service primarily based on the concept recipients — not senders or platforms — ought to be compensated for his or her consideration. That concept didn’t take off, however a device that they constructed to search out potential clients turned the muse of SeekOut.
SeekOut has raised a complete of $189 million from traders together with Tiger International, Madrona Enterprise Group, and Mayfield, hitting a $1.2 billion valuation with its Sequence C in early 2022. It grew quickly and expanded headcount, however reduce employees twice — in October 2023 and Could 2024 — because the economic system turned and the recruiting market contracted.
As we speak it has roughly 150 workers, greater than 750 company clients, and over $100 million within the financial institution, in keeping with Gupta. That provides SeekOut the runway to deepen its AI initiatives and time to pursue the acquisitions Thompson described as central to his plans.
SeekOut ran a proper govt seek for greater than six months, however Thompson didn’t come by way of that course of. He was initially introduced in as an advisor on SeekOut’s acquisition technique, by way of connections together with SeekOut basic counsel Sam Shaddox — his exterior counsel through the sale of Nuiku — and the Seattle M&A advisory agency Alexander Hutton, the place his brother James Thompson works.
By that advisory work, Thompson linked with Bala, and the CEO dialog advanced from there. “It clicked, and moved simply very quick,” Gupta mentioned.
SeekOut operates in two areas: Recruit, an AI-powered platform that recruiters can use to look greater than a billion candidate profiles; and Spot, the service that pairs AI brokers with SeekOut’s personal recruiters to ship interview-ready candidates to hiring managers in about two weeks. Beneath Thompson, Spot is predicted to be the most important focus.
As govt chairman, Gupta estimates he’ll spend 20% to 25% of his time on the function. Extra broadly, he mentioned, he worries in regards to the societal influence of AI, and desires to make extra time for the issues expertise can’t speed up, resembling household, relationships, and neighborhood.
“Tomatoes don’t develop any quicker,” he mentioned. “They nonetheless take a season to develop.”
