Anoop Gupta

Anoop Gupta is co-founder and chief executive of SeekOut, a Bellevue, Washington, company whose AI talent platform helps recruiters find, hire and keep hard-to-find technical and diverse candidates. Born in Delhi, India, he was a Stanford computer science professor, a startup founder and an 18-year Microsoft executive before he started SeekOut.

Growing Up Across India and Africa

His father's job moved the family to a new place every three or four years, including time in Africa, and he went through several new schools, including a boarding school, he told the Dealmakers podcast. He credits those moves with teaching him to adapt and make friends quickly. He earned his engineering degree at the Indian Institute of Technology, where 32 of the 42 students in his class went on to study in the United States.

He came to Carnegie Mellon University for his Ph.D. in computer science and met his wife there. He then joined the Stanford faculty, which he loved for its mix of teaching, research and startups, since most of his professors had tried companies of their own.

Teaching at Stanford Before VXtreme

After he earned tenure, his department head John Hennessy, later Stanford's president, told him to "just go do it" and start a company, since he could always return. With graduate students who had been researching internet video, he co-founded VXtreme with Diane Greene, who later co-founded VMware. They bootstrapped with angel money, signed CNN as their first customer, and sold the company to Microsoft in 1997, about a year and a half after launch.

The lesson he took from VXtreme was about technical founders. He has said they need to "focus and understand the market," including demand and product fit, and that first-time founders have to learn to grow the whole pie together before they worry about their own share.

Working Beside Bill Gates at Microsoft

He spent 18 years at Microsoft, according to his Microsoft Research profile. He was a Distinguished Scientist at Microsoft Research leading telepresence and natural user interface work, reported directly to Bill Gates as his technology assistant, ran Exchange and Skype as corporate vice president of Unified Communications, and later served as corporate vice president for global technology policy. Before Gates left for his reading weeks, Gupta pre-read and picked what he would read, and Gates coached him on pitching to Steve Ballmer.

Pivoting from Career Pathways to Recruiting

Gupta has compared Microsoft to an 18-wheeler truck. In 2015 he and his co-founders left to be more like mountain bikes, he said, and to build the precursor to SeekOut. Their first product mapped career pathways, such as where Facebook user interface designers went next. Recruiters found that data so useful that the team pivoted into talent acquisition, as he told Madrona.

His co-founder Aravind came from building the Bing search engine, and Gupta's own doctoral work was on AI and systems. SeekOut grew to about 1,000 customers and widened from a sourcing tool into what it calls a Talent 360 platform for hiring, developing and keeping employees.