Oleg Rogynskyy of People.ai: ‘I had a gut feeling that a war was going to start’ – Financial Times

At the start of the year, one honeymooning Ukrainian engineer received a call from his employer. Would he like to extend his holiday in Turkey, all expenses paid? Yes. Of course.

Such freebies were part of a strategy by People.ai, a tech platform providing data on sales and operations performance. The aim was to persuade its Ukrainian staff to leave their country weeks before Vladimir Putin announced Russia would deploy a “special military operation” in Ukraine. Many employees were sceptical and scared, says Oleg Rogynskyy, the founder and chief executive who grew up in the industrial central-eastern Ukrainian city of Dnipro. The city is now strategically important, located between the three main areas of fighting.

“We set up an incentive structure [offering] free vacation,” he says. “Carrot, stick, you name it. We were pressuring our employees — the [Russian] rhetoric was escalating.” Once a critical mass left, he says, the rest followed: most of his 42-strong Ukrainian workforce — about a sixth of his staff — left by mid-February.

It was a strategy 35-year-old Rogynskyy had rehearsed with his own parents. “They were kicking and screaming, nobody was believing me that something is going to happen.” So instead of persuading them to flee, he offered a trip to visit him in California, where People.ai is based. His parents are still there.

Rogynskyy, who speaks carefully in English, is in London after meeting a client and is wearing a crisp shirt and matching neat haircut. He had some experience of having a small team in Ukraine in 2014 when conflict broke out following Russia’s annexation of Crimea. It made him develop a “gut feel of what it looks like when the war is about to start”. 

In November, as intelligence reported Russian troops were deployed at the border, he established a working group with his chief technology and human resources officers, and chief of staff who used to be in the US military. The next month, as Russia’s demands escalated, including barring Ukraine from joining Nato, People.ai held daily meetings, planning scenarios around an invasion. “We weren’t sure how [the] EU [was] going to react to a Ukrainian refugee crisis,” says Rogynskyy. “We have an office in Prague but we weren’t sure if [it] was going to have [an] open border with Ukraine when millions of people are arriving.”

So they set up outside of the Schengen Zone, initially in Zagreb, and instructed Ukrainian staff to ensure they and their families had passports, US dollars and paperwork, in preparation to leave the country. Employees were sent screenshots of Google Maps showing the best routes out. Costs relating to passports, transport, mobile calls and housing were paid by the company.

Financial and productivity risks, says Rogynskyy, came with pushing staff to leave, but there was “also a reputational risk”. What if he disrupted employees’ lives for no reason? “Unfortunately, those risks ended up being worth taking.” Most businesses with Ukrainian staff, he says, “were completely caught off guard”. Subsequently, he has distilled his experiences and shared best practice with other companies.

His experience in 2014 had taught him that in “the moment of doubt and stress and danger your judgment might be clouded by events” and that it was important for the company to have a strong culture and not depend day-to-day on directions from the top.

A few employees have returned and joined the war effort. People.ai engineers, he says, were unofficial “beta testers” of Starlink, Elon Musk’s satellite-based internet service, providing connection across parts of Ukraine. “Our engineers have come up with the field guide for using Starlink, [with] ways to better camouflage these bright white dishes.”

Rogynskyy, who grew up speaking Russian, helps co-ordinate tech contributions from Silicon Valley to support the campaign by Ukraine’s president Volodymyr Zelenskyy, who is from his hometown. He is fully aware of the risks his compatriots are taking. His best friend, a single father who works as a doctor, is on the frontline and has been sending pictures, “sacrificing his own life for the lives of others”.

Some Ukrainian employees feel guilty about leaving Ukraine. He reasons that they can join the war effort on full pay, or “you can help us keep on going and pay taxes and hire more Ukrainian folks and help rebuild”. This is both pragmatic and self-serving. The private company’s latest round of funding last year valued it at more than $1bn, making it a tech “unicorn”, and it wants to capitalise on the technological changes in the working world wrought by the pandemic.

Born to a modest middle-class family, Rogynskyy’s father was an entrepreneur, but “never very successful”, while his mother studied economics. “She basically studied the [Soviet] system that no longer existed after 1991, so she ended up being a stay-at-home mom and a small business operator.”

In the last year of school he won a competition to study in Broadstairs, Kent, south-east England, encouraged by his parents who wanted him to “get a western education”, which he continued, studying political science at Boston University. “They were very happy in the beginning [when I left Ukraine]. But then when I didn’t come back for 20 years they were a little bit less happy.”

Facebook (“my first experience with truly viral technology”), originating from nearby Harvard University, inspired Rogynskyy to start his own social media site (that ultimately was unsuccessful) before going on to work in sales for a technology company in Canada. That experience made him realise his peers failed to learn effectively from “past mistakes”. Collecting data is “considered a chore”, he says, compared with “wining and dining customers”. “But the only way to improve is to understand what you did in the past, what worked, what didn’t, and how to make it better.”

In 2011, he started Semantria, which applied machine learning to the legal industry. A few months later he fell from a balcony when a railing collapsed, sustaining 23 fractures and resulting in hospitalisation for six months. To distract himself from his injuries, he continued working from his hospital bed. Three years later, he sold the company to Lexalytics, a US text analytics software group.

Three questions for Oleg Rogynskyy

Which leader do you most admire?

President Volodymyr Zelenskyy has shown me what it means to be a true leader as he’s navigated this crisis from the front lines . . . not from behind the Kremlin walls as in others’ case.

Biggest business mistake?

I started my previous company, Semantria, in too small a market (sentiment analysis in the cloud), which is very hard to correct later. When launching a company, you can find a way to improve your team and product, but it’s very hard to pivot away from the market you picked.

Productivity hack?

I fly a lot for work and am religious about preparing a comprehensive plan of what I want to accomplish on every flight.

Combining his lessons from his first sales job and running a technology company, in 2016 he started People.ai, applying machine learning to sales performance. The way he explains it to sales teams is by comparing it to Moneyball, the application of data to baseball. “Can you be a professional sportsperson without tracking and improving on your performance? No. Well, you are an athlete in the business here, . . . [using] the AI to understand your performance [also] leads to you making more money and the business being more efficient.”

Such analogies tend to only go one way, I suggest. Sales teams love to see themselves as athletes, sports stars tend not to find the reverse flattering.

At the onset of the pandemic, the company laid off 30 people. They started hiring again later, boosting the workforce to 250. One area he managed to save on was office rent. At the start of 2020, he had been on the brink of signing a new lease when his wife, an infectious diseases doctor, warned him about an emerging virus. “We pulled out from the office and saved a lot of money.” It is proving hard to bring workers back to their newly opened office in San Francisco now. However, changes in working patterns after the pandemic have helped the company as workers have become more comfortable with technology.

“People are not afraid of [machine learning. They] understand how it works and how it’s going to benefit their performance.”

Nonetheless, he admits that the war after two years of a pandemic has taken its toll. “There was a moment where I came home and . . . I felt so helpless. I sat down on my porch and, I don’t do this often, but I couldn’t hold [back] tears.” At that moment his best friend called and ticked him off for self-indulgence. “That was really helpful, ” he reflects. “I got a lot of motivation from that.”


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