"I Was Not Playing the Long Game" -- Prem Kumar, Co-Founder and CEO of Humanly

Podcast

Ten Years at Microsoft, One Side Bet at a Time

Prem Kumar spent about a decade at Microsoft, working across HR technology, LinkedIn data integration, and other product roles. His interest in HR issues showed up early, through Microsoft's Think Week format, where any employee could write a paper on a topic and get it voted on by peers. Prem wrote his about engaging millennials in the workplace, and then-CHRO Lisa Brummel commented on it, a moment he says convinced him he was onto something. Brummel later became an advisor at Humanly.

The paper also led a Microsoft director, Ross Smith, to reach out and ask Prem to be his mentor, which turned into a formal reverse mentoring program: junior women mentoring senior male engineering leaders on how to better engage the broader workforce. Prem said that same instinct, that title and tenure don't determine who has something to teach you, carried straight into how he built Humanly's culture.

"I think part of that is realizing that anyone at the company can mentor me on something."

-- Prem Kumar

While still at Microsoft, he also built a side project mapping apartment listings against Google Maps data, an early rental search tool. It folded, largely because, as Prem put it, they figured if they built something cool people would come, which isn't how marketing or SEO works. He said learning to let go of something that wasn't working became one of the more useful skills he carried forward, and it set up his move to TinyPulse to learn the pace of startup life before starting his own company.

Betting on Recruiting Tech

Prem traces part of what became Humanly to his senior year at the University of Washington, when he and a female classmate with nearly identical resumes and internships interviewed with the same companies for the same jobs. Comparing notes afterward, they found the two candidates on paper looked interchangeable, but the interviews didn't treat them that way.

"We were being interviewed completely differently, so they would grill her on a lot of technical skills, but somehow by looking at me, they thought that I was very technical."

-- Prem Kumar

That observation sat with him for roughly a decade before he acted on it. When he did, he brought on two co-founders: Andrew Gardner, whom he'd worked with at TinyPulse and who understood the buyer side of the business, and Bryan Leptich, an engineer he'd worked with on the earlier rental project.

"So I took him to Applebee's and paid for his Applebee's dinner and convinced him to join."

-- Prem Kumar, on recruiting Bryan Leptich

Humanly started by using chatbots to move candidates past the resume, giving them a two-way conversation before a human ever got involved. That grew into full interviewing and screening at scale, the product Humanly runs today.