People.ai

Oleg Roginski came to People.ai after a successful exit with Cementria, a cloud-based sentiment analysis API he bootstrapped to $5 million ARR in roughly three and a half years. While at Cementria and Lexalytics (the acquirer), Oleg spent nearly a decade in enterprise sales. He noticed a persistent frustration: salespeople hated data entry. "I dreaded the most was doing the work twice," he explains. "First, you talk to a customer, and then you log that data into Salesforce. You have to literally type it up or do a bunch of clicks without actual purpose." More importantly, he realized sales leaders had almost no reliable data about their teams' performance because it all relied on manual entry. There was an insight buried in his pain.

Oleg's co-founders at Cementria knew he had a track record, so they trusted him to pivot toward this new problem. He spent the crucial early weeks doing something most founders skip: extensive customer development. He talked to 100 VP of Sales and hundreds of salespeople in a short period, recording conversations, transcribing them, and taking 5-10 page prep documents for each meeting. Two weeks into this research, he had an "aha moment." Working from the back end of a previous product, the team rebuilt the front end and shipped a simple real-time dashboard showing what sales teams were actually doing—pulled from Salesforce, email, calendar, phone systems, Zoom, Webex, and other tools. No complex features. Just visibility.

Oleg didn't have to hunt far. He returned to the 100 VP of Sales he'd already been talking to. "If you talk to someone, ask them really smart questions, hear them out. And then two weeks later, you come back with a working prototype of exactly what they wanted, but not necessarily even told you. You know what they're going to do? They're going to pull out credit cards." The result was stunning: nearly 100 logos in the first 45 days, right before Y Combinator demo day. This early traction led directly to a Series A round. Oleg never relied on inbound marketing or paid acquisition—just outbound sales and the network effects of being genuinely helpful.

The secret wasn't the product features; it was the sales methodology. Oleg refused to show a demo until the third or fourth conversation. Before that, every call followed a rule: ask five questions for every one answer you give. "If you're staying in the discovery mode like that, your learning rate will be much, much higher." He prepared obsessively—reading blogs, Twitter, researching backgrounds, finding mutual connections, even identifying personal interests like basketball to match the right salesperson to the right prospect. He taught every team member this consultative approach rather than traditional closing. The key insight: "If you are creating social capital for them, they'll introduce you. If you're burning their social capital, they will block you."

People.ai now has 55 people (growing to 100) and works with a significant number of public companies and large enterprises. While Oleg declined to share exact revenue figures (citing "in flight" fundraising), he confirmed the company has raised more than the $7 million mentioned earlier. The focus shifted from SMB dashboards to enterprise needs—larger companies need data-driven insights far more than smaller ones. Oleg continues coaching other founders on sales process, embodying the philosophy from Ben Horowitz that drives him: "take care of the people, the products, and only then the profits in that order."