Q&A with Oleg Rogynskyy, Founder & CEO of People.ai on Team and Company Building

Nakul Mandan
May 21 · 6 min read

People.ai is announcing its $60m Series C financing this morning. When we first led the company’s Series A financing, the company had 5 employees. Since then, Lightspeed has been fortunate to have had a front row seat to how founder and CEO Oleg Rogynskyy has been building the team and company from the ground up.

Since our initial investment, Oleg’s vision for the company has only expanded, but what has been equally exhilarating to see is how he’s grown as a CEO and a leader. The aspect that has really stood out for me is how from Day One, Oleg has always made decisions based on what’s best for the long term. Whether it be team construction or product decisions, whenever there’s been a trade-off, he’s chosen what is right for the company and its future.

In honor of today’s news, we sat down with Oleg to discuss his thoughts on team and company building. Below are highlights from our conversation and we’d love to hear what you think in the comments.

Tell us about your journey, and what inspired you to build People.ai.

Early in my career, I joined a company called Nstein Technologies as the first inside sales rep. One day our COO grounded the entire sales team for a week to clean up every record in Salesforce because our data was, to put it mildly, garbage. I hated every minute of it, and it felt like a complete waste to take us away from revenue-generating activities for an entire week.

That company was acquired in 2010, and in 2011 I started my own company Semantria. Ironically, I also had to ground my sales team for a week to clean up our CRM data. And after I sold Semantria in 2014 and became head of sales at a company called H2O.ai, I experienced the same issue again.

That meant that in nearly a decade, nothing had changed in the CRM world. People still had to manually enter data into Salesforce, and it was a mess. I knew there had to be a better way, so that’s why I decided to start People.ai.

Where does your product have the maximum impact for your customers? Why is it so valuable across the enterprise?

Salespeople are notoriously bad at entering data into their CRM. So, say every salesperson meets 100 people per month, but they only enter 20 contacts. That means companies lose 80% of their pipeline. And the larger the company, the more resources they’re deploying, so the higher the cost of that data loss. We bring together all the data that is relevant to sales and marketing teams to one unified platform, and auto-populate CRM, marketing automation and other systems to remove the need to manually enter data into your systems, which saves reps approx. 20% of their time but more importantly, it captures more data and more accurate data. But that’s just the beginning. Making use of all that data by running analytics on it has a high ROI for enterprises, and helps them become more predictive and agile.

Initially, we were only selling to sales managers, but we learned there was a huge value for marketers and customer success teams, too. Everyone outside of the sales organization was excited to know what their salespeople were doing. If marketers are able to uncover those 80 contacts and put them into the funnel, that means a lot more prospects eventually get into the sales pipeline.

Given the scale of the vision you have for People.ai, what were some of the key components of architecting the product and the company for that scale on Day One?

That’s a really good question. We follow three core principles when designing our product.

The first is based on three network effects: data network effect, product network effect and ecosystem effect. Data network effect means if we have more data, the data we give customers is better. Product network effect means the more data we have, the better the product works. And ecosystem network effect means the more data we have, the bigger and more valuable the ecosystem becomes. So we designed People.ai to have all three network effects from day one.

The second principle is that we built in ecosystem enablement right away. We don’t fight other companies, and we don’t try to carve out our own territory. Everything we do is open. For example, people ask us if we compete with Salesforce — and we don’t. In fact, we want to be Salesforce’s best friend. By solving Salesforce related pain points, we make it more valuable, which makes People.ai more valuable. And we have the same relationship with pretty much any other big system we play with.

The third principle is to be completely invisible to the end user. We don’t want our users to need training, or to have to install new apps or plugins — they have enough. We are completely invisible in the background, collecting the data and delivering all the value.

You’ve put together a really strong exec team around you. Can you talk about how you think of building out an exec team and the board?

From the very beginning, I tried to hire people who were as senior as I could get. Because if you’re in hypergrowth mode, you’ll be growing faster than even the smartest person’s learning rate. So the only way to grow really fast is to hire people who have seen it before. Then your business is not growing at the rate of them learning, but at the rate of people who have already learned from their experience and are not making mistakes. That’s how we were able to go from zero people to almost 150 in three years (which is pretty insane!). And the added benefit is that having senior people on the team frees up time for the CEO to focus on other things that need attention.

Then to create a board, you have to think about your 18-month needs. For Series A, we partnered with Lightspeed Venture Partners because they’re known to be relationship people. Their value add is that they’re going to be by your side and helping you on a personal level. And literally for the first year, I was on the phone with Nakul pretty much every night as I drove back to Palo Alto, discussing our product, pricing, and GTM strategy.

For Series B, we brought on Peter Levine from Andreessen Horowitz, who is known for turning any potentially antagonistic opportunity into a partnership opportunity, which has been really good.

Then Godfrey Sullivan, who grew Hyperion Solutions to a billion-dollar company and led Splunk to a successful IPO, joined as an independent board member. Every time we talk, it’s a learning experience. I say “Godfrey, have you done this before?” And he says “Yeah, nine times. I screwed up seven times, semi-screwed up once, but here’s how I didn’t screw it up. You should do it this way.”

And now with our Series C, we brought on Will Griffith from ICONIQ Capital. I didn’t have experience building a world-class product marketing organization, so I was very intentional about who would join the board, and product marketing is Will’s superpower. It’s a match made in heaven.

How have you grown as a CEO over the years? Can you talk about some of the mistakes you made early on, and how you think about your growth as a CEO going forward?

Early on, the mistakes were about not asking for or listening to advice. Today, we’ve got such an experienced board, so it’s important for me to listen to them and actually do what they say. I really like the saying “You have two ears and only one mouth for a reason.”

Another learning was to focus on culture. When we designed our core values early on, it felt easy — we just pumped them out in a day. Now I wish we had put a bit more thought into them, because today People.ai has our official core values, plus some “unofficial” ones that have popped up, which can be confusing. So a bit more thought there would have been very helpful.

The last learning is to never settle when it comes hiring. If you don’t like anyone in your current group of candidates, just keep looking. It’s worth waiting to find the best of the best.

Lightspeed Venture Partners

Lightspeed is a VC firm focused on accelerating disruptive innovations and trends in the enterprise and consumer sectors. Lightspeed has backed 350+ companies globally in the past two decades including Snap, Honest Co., GIPHY, Nest, Nutanix, AppDynamics and MuleSoft.