The early 2000s were a monumental time for technology. In 2001 alone, the release of the Apple iPod kicked off the world’s first step toward mobile-first, Microsoft changed gaming forever with Xbox, the first gaming console with high-quality graphics fueled by GPUs, and Steven Spielberg released a film called A.I. Artificial Intelligence. And in September of that year, future People.ai founder and CEO Oleg Rogynskyy got on a plane in his native Ukraine and set out for a new life in Boston, Massachusetts.
At just 15 years old, Rogynskyy was accepted to the prestigious Boston University (BU) as an undergraduate student, all the way from Ukraine. For a young man who had grown up reading adventure books and spending summers outdoors in the Ukrainian countryside, starting the next chapter of his life in America made perfect sense. “I have two core values that are always in my mind,” said Rogynskyy. “‘Do your homework’, and, ‘move without hesitation’. A lot of who I am was shaped by how I grew up.”
These values would propel Rogynskyy as he struggled to keep up with BU classes taught in a language he wasn’t yet proficient in. They would drive him to start his first successful company just 10 years later and then keep going after getting into a near-death accident a month after launch. And they would be the catalyst for placing a big bet on data at People.ai.
The Oakland A’s of AI
In 2016, Rogynskyy founded People.ai to help companies solve a critical problem in their sales organizations. One that he experienced firsthand throughout his sales career: a customer relationship management (CRM) tool filled with incomplete and inaccurate data from sales teams. Besides being quite technical, Rogynskyy is a seller in his DNA (if you ever have the pleasure of watching him pitch a customer, you’ll understand what I mean) and he knew that what reps want more than anything is more time to spend with customers. But the manual data-entry parts of their jobs were keeping them from doing that - when they made time to enter data into the CRM at all.
From a business perspective, all that seller activity data contained some of the most valuable insights across customer interactions, deal cycles, and sales tactics, that were critical to understanding and optimizing the go-to-market (GTM) functions of the company. People.ai was designed to solve both problems but with a much larger goal in mind. From the beginning, it has automated the sales activity and persona data collection, cleaning, and matching process so organizations would be ready to capitalize on AI when the time was right.
When Rogynskyy founded People.ai, other point solution go-to-market technology companies were focused on addressing limited parts of a sales process, such as call recordings or forecasting. But Rogynskyy intentionally founded his company with a focus on data collection, organization, accuracy, and enrichment across the entire go-to-market (GTM) function. It was a big bet based on a hunch that artificial intelligence (AI) technology would one day progress to a point where that data would suddenly be the most valuable currency in business, and sales activity data would be priceless for optimizing enterprise go-to-market. “I don't believe anybody else had that idea until AI really hit us hard about a year ago,” he said. In 2024, after nearly a decade in business, Rogynskyy’s big bet on data is paying off.
Rogynskyy becomes passionate and focused when he talks about AI and the importance of establishing a data culture at companies. The implications of AI have been obvious to him for a long time. And to some of People.ai’s earliest customers as well. “The feedback from our earliest customers was interesting because companies who got it were saying ‘We need to future-proof our business’,” said Rogynskyy. “They understood that there is a winner-takes-all dynamic that's built into AI. They were very clear on the fact that, if we have not collected the data and then our competitor has collected the data? There's nothing we can do to catch up. Take the story of “Moneyball” and the Oakland Athletics. How did the baseball teams that did not collect the data feel when they were playing against Oakland A's? As a long time baseball manager once told me, playing the A’s back then felt like showing up on a bicycle to a Formula 1 race.”
One of Rogynskyy’s superpowers is his ability to connect with customers. “Throughout my career, I learned not only how to build AI products, but also how to explain to customers what AI is in very simple terms,” he explains. “Connecting with customers and helping them understand the power of AI to future-proof their business fuels me. It's a joint win and I love that." But Rogynskyy credits Sam Altman and OpenAI with making AI suddenly accessible and understandable to everyone. This was not always the case, especially in 2016 when Rogynskyy first started selling the People.ai solution. Incidentally, People.ai, OpenAI, and ScaleAI were all in the same Y Combinator batch in Summer 2016. It was a good year for AI.
“Back then there were a lot of people saying, ‘Why do we need to collect this data? We're playing our game just fine based on hunch and intuition’,” said Rogynskyy. “But the ones that ‘got it’ and started working with us early have now collected massive decade-long datasets of all their go-to-market telemetry. And even the best business intuition can't compare to the real advantage offered by a huge data moat. These companies have now walked into the age of AI with massive advantage. That data set is probably the most valuable thing a company could have right now.”
Learning the Power of Resilience and the Value of Intentionality
Rogynskyy founded People.ai with a very clear vision thanks to his experience with his first start-up, Semantria. Founded in 2011, Semantria used the [back then] latest in AI to automate sentiment analysis for customer feedback collection, survey results, and social media posts to understand customer sentiment at massive scale, powering the likes of Salesforce, Sprinklr, Hootsuite, and Microsoft.
A month after founding the company, Rogynskyy was in a serious accident that landed him in the hospital for a month and in a wheelchair for six months after that. This was his hard first lesson in really valuing each moment you are given. In the midst of recovering, he faced a huge decision that would have a lasting impact.
“Not long after the accident, I realized I was going to have to pay a lot of medical bills because I was not a United States citizen. And Semantria was bootstrapped so I was running it off my credit cards,” recalled Rogynskyy. “And that was the moment when I could have pulled the plug on the company because it was only a month old. But instead, I kept going. I spent months ‘smiling and dialing’ from the hospital bed and actually pitching customers, as there was not much else to do during that long Montreal winter. By the time I was out of the wheelchair we had over a million dollars in revenue.”
Rogynskyy drew on the values he developed in childhood to get him through the experience: do your homework and move without hesitation. This ability to keep working hard and moving forward paid off. Despite operating without outside investment and the accident, Semantria grew its revenue by 600% in 2013. He successfully sold the company to Lexalytics in 2014.
Rogynskyy credits the accident and subsequent recovery in 2011 with teaching him to value the preciousness of time. “That was a very defining moment for me,” said Rogynskyy. “Now, I keep this poster called ‘My Life In Weeks’ by my desk, which shows you exactly how many weeks you have left in your life. It puts everything in perspective. Every time you color off a week you’re reminded how quickly time passes. That week is gone forever, are you happy with how you spent it? What will you do differently next week, to make sure the answer is a resounding, ‘Yes!’?”
The Future of AI is Coming (Whether You’re Ready or Not)
Rogynskyy likes to compare the future of AI automation to self-driving technology. The Society of Automotive Engineers (SAE) and a company called Synopsis created a great framework for the Levels of Driving Automation.
Inspired by this framework, Rogynskyy wanted to translate it to the levels of AI automation for GTM teams. He coined it "GTM AI Maturity Levels."
Here is his explanation:
"Level 1 is minimal automation, where technology is layered on top of existing manual processes.
Level 2 is partial automation, where data is collected from many different sources and automation might be in place across different systems but there is no centralized platform to bring them all together.
Most companies are operating at Level 2 today. The disjointed nature of Level 2 automation is why many sales technology tools get a bad reputation - even the good ones. A mediocre AI tool is the level 2 tool that's being sold as AI but actually isn’t AI at all. Many of these tools are just adding an extra AI button that accelerates a few steps of a workflow for the end user but lacks sufficient data to provide true value.
Level 3 is advanced automation where data is no longer siloed and AI, being the central “brain” across all automations, assists the user with many day-to-day tasks. In the self-driving car analogy, it was the addition of dozens of sensors built around the car to capture real-time data about the car’s surroundings and a central AI interface built into the car that has allowed it to have self-driving capabilities. This is where users start getting that "ah-ha" moment with AI and buy-in. For those who have ever experienced Tesla’s self-driving capability on the highway, that’s the “wind through your hair” moment when you see the car driving itself for the first time.
Level 4 is advanced automation where AI generates actioning outputs and next steps. But we're not quite there yet.
Level 3 automation is possible today with the right data foundation in place. AI will advance to Level 4 – putting AI in the driver’s seat – within a couple of years. It's scary, but I believe it's inevitable. And if we think back to people who were scared of cars and just wanted to keep riding their horses everywhere. Were they able to keep up with their competitors who were now driving around? Or companies who didn't take the internet seriously. Netflix ditched the horse. Blockbuster did not."
Despite AI’s reputation, Rogynskyy says it’s not as complex as we think. “AI is not that hard,” he explained. “It’s binary. Pretty much every tech company is using the same kind of AI technology to build their products and it's going to keep on converging. What most companies don't have is the data foundation that will produce accurate outputs to actually help you run your business smarter and faster.”
Work Hard. But Don’t Forget to Do Cool Stuff.
Rogynskyy would tell you that he doesn’t have much time for anything outside of running People.ai and spending time with his family. But one of the underlying themes of our conversation were the people and experiences that he draws inspiration from.
He credits his wife, Jassi, with teaching him that he can make the biggest impact when he focuses on the things he feels most passionate about. She demonstrates this through her work in the biosecurity medical field. He counts former Microsoft Chairman and ex-CEO of Symantec John Thompson as one of his mentors and says every meeting with him is like getting a mini MBA. And he values advice he received from a longtime CEO friend for running his business. “His two rules are: do really cool stuff and don't die,” said Rogynskyy. “As long as you are doing really cool things that are exciting for you, and you do them for long enough, luck will turn your way and very good things will happen. And on the contrary, if you are not seeing success, evaluate if you are actually doing both of those things.”
He also shared a habit that may be surprising for the founder and CEO of a tech company on the cutting edge of AI. One who likes to joke about how the advancement of AI will eventually free up enough of his time to allow him to spend more time on the beach drinking mojitos. “It turns out that writing down what you need to accomplish on paper is a very strong psychological anchor to get it done. I carry my notebook and a pen with me everywhere for that purpose.”
Learn more about AI Maturity in your sales organization by taking the GTM AI Maturity Assessment.
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