The Story Behind My Investment In People.ai
A few years ago, during a YC cohort (before Demo Day), a few sources told me about a SaaS founder in the batch who was on a mission. Once I hear a name or company a few times in a short period, I begin to investigate. Within a few days, I got connected to Oleg from People.ai, and he immediately put me to work.
Oleg is a learning machine. In the very early days of the company, Oleg immediately demonstrated to me an intense desire to learn, to listen, and to sharpen his craft. I am not surprised that today, he is making a big announcement for the company’s new financing round — People.ai raised their Series B led by Andreessen Horowitz (this comes after the Series A led by Lightspeed, where I am a Venture Partner, a few years back).
You can and should read about what People.ai does, and you can find that information here and here. The company has 100 employees, is growing revenue at an impressive clip, and Oleg and his team show no signs of stopping on their mission to bring artificial intelligence to the CRM, improve sales processes, and ultimately measure the bottom-line impact of these activities for their 50 enterprise tech customers.
On this blog, I want to simply highlight that in my five-plus years of investing, Oleg is simply one of the most driven, most aggressive, most focused founders I’ve had the pleasure of backing. I have spent a ton of time with Oleg (this doesn’t the count the 30-100 text messages he sends me per month — sorry Oleg!), and I have never once seen or heard him complain about the fight he has ahead of him — instead, he finds it fun, like a game he has to master. He thrives on the challenge. In helping Oleg secure his Series A with Lightspeed (with Nakul Mandan on the board) and then helping him connect with our friends at a16z (Peter Levine), it was easy to introduce Oleg and vouch for him. No slide deck was needed for the introduction. Instead, I just recommended Oleg with the description I used above. In many ways, despite all the blog posts, tweets, and panels on Series A financings out there, all founders really need to get to the next round is a hard-earned recommendation.