Behind the Curtain: Why We Selected Ukraine-born Headway Inc

After Russia launched its full-scale invasion of Ukraine, the world opened its doors to a flood of Ukrainian refugees searching for safety. However from London, one Ukrainian founder was fighting to go in the opposite direction.

Anton Pavlovsky, Founder and CEO of Headway Inc, a global tech company that provides lifelong learning products, was living in the UK in February 2022, but the invasion galvanized his return to his home country. He helped organize his team’s relocation and then returned to Headway Inc’s office in Kyiv, where he joined the majority of his company. In fact, many of Headway Inc’s Ukrainian employees also stayed, offering a story of resilience and strength in the face of war. Years later, during Anton’s interviews to become an Endeavor Entrepreneur, he was asked the fairly routine question, “What keeps you up at night?”

“Well,” he said. “Rockets and missiles.”

A month after he founded Headway Inc in 2019, Anton discovered a podcast with Endeavor CEO Linda Rottenberg and Reid Hoffman and shared it with friends. But Endeavor Ukraine hadn’t opened its doors yet. Little did he realize that Headway Inc would go on to become Endeavor’s first Ukraine-born company. 

It is also one of our Outliers this year, top-performing companies in Endeavor’s portfolio chosen for their ability to set new standards of success in regions beyond Silicon Valley. Despite Russia’s ongoing invasion of Ukraine, Headway Inc has sustained healthy growth with over 150 million users worldwide. And that’s only the beginning of their journey.

A company built on resilience and growth

Anton Pavlovsky studied engineering, started his career in investment banking, and then shifted to IT, where he quickly secured the position of Chief Product Officer. He is a serial entrepreneur. Before founding Headway Inc in 2019, he launched a startup in the social discovery space and guided another embryonic startup to the top of its sector.

Throughout his diverse career, Anton has always been passionate about self-education. However, at some points, his busy schedule left him with little time to expand his knowledge. This led him to recognize that millions of adults worldwide faced the same challenge.

“He realized that he was in a privileged position to have the time, energy, and resources to focus on self-growth. The majority of people around the globe don’t have that. That’s where he got the idea for Headway Inc, with the thesis that even if you only have fifteen or ten or even just three minutes a day, you can still use it to learn to become a better version of yourself,” says Sviatoslav Sviatnenko, Managing Director at Endeavor Ukraine.

One question he encountered became the last straw. “What would you do with your life if you knew that you were guaranteed success and happiness?” He answered:

Headway Inc offers digital and physical products that make lifelong learning accessible, personalized, and impactful. In 2019, a small, bootstrapped team of three led by Anton Pavlovsky launched the Headway app, armed with a vision to redefine the way people learn and grow. Born in Ukraine, the company has been global from day one. The Headway app quickly gained leadership in the book summary niche worldwide and, later on, expanded into the broader lifelong learning space.

Previously known as Headway, the company has officially evolved into Headway Inc. The new identity marks the company’s transformation into a full-scale consumer tech platform. Now, five distinctive brands are integrated into its structure, along with several running R&D initiatives. One app, Impulse, offers brain “workout” puzzles to target different brain areas like memory or concentration. Another app, called Nibble, features short lessons across STEM subjects and the humanities, while AddMile platform helps users improve their personal and professional lives through coaching.

Headway, the company’s flagship, is the world’s most downloaded book-summary app, boasting more than 50 million downloads across the App Store and Google Play. With a revenue model based on recurring subscriptions, the company’s “secret sauce” is its quantitative approach to product development, processing petabytes of user data annually to drive every decision with meticulous attention to customer experience.  For instance, the Headway app is ranked among the top 10 highest-grossing iOS apps in the education category worldwide.

“Headway Inc is obsessed with customers and data,” explains Carlota Entrecanales Carvajal, Endeavor’s Manager of Entrepreneur Selection. 

The rich pool of data Headway Inc gathers while engaging with its users through the diverse portfolio of products creates an internal, comprehensive understanding of what learners need and what approaches are most effective, ensuring the most promising opportunities for new product launches.

The right connections, the right time

Anton made an impression on everyone from Endeavor. Joanna Rees, impressed by Anton’s empathy and strategic thinking, called him “Gandhi meets Machiavelli.” Binny Bansal, former Chief Operating Officer and then CEO of e-commerce company Flipkart, called Headway Inc an “incredible business”: an impressive compliment from the man who led India’s largest tech deal to date when Flipkart sold a controlling stake to Walmart for $16B in 2018.

During Anton’s International Selection Panel, he shared an internal Headway Inc policy where anyone who has worked for more than five years at the company is entitled to a full month of paid sabbatical leave. One of the panelists interviewing Anton, co-founder and CEO of Portuguese fintech Coverflex Miguel Santo Amaro, was so impressed with the idea that he promptly introduced it at Coverflex. Even before officially joining Endeavor, Anton had showcased his ability to influence and empower entrepreneurs everywhere.

It’s a quality we look for, something we call the Endeavor Multiplier Effect™, where the work we do with entrepreneurs is paid forward by training, mentoring, and investing in the next generation of founders. Anton’s ability to advise and mentor other entrepreneurs and his passion for building up Ukraine’s tech scene makes him an obvious pick for an Endeavor Entrepreneur.

But Headway Inc is also at a critical juncture where Endeavor’s support is crucial. The suite of products has been very successful in building customer loyalty and growth, but requires extra effort to connect the variously branded and named apps under one strong brand of Headway Inc while maintaining differentiation. It’s a strategic question that Endeavor’s team and connections, including Joanna, are already working with Anton on.

And while Headway Inc has already proven its success, Anton’s ambitions are set even higher: he wants to take the company public in an initial public offering (IPO). That means careful and strategic venture opportunities along with mentorship as he builds Headway Inc to that point. Already, Endeavor has connected Anton with Vargha Moayed, Chairman of Endeavor Romania’s board and the man who helped software company UiPath scale from $1M to $1B in revenue on their path to their IPO. When Headway Inc launched their Madrid office, Sviatoslav Sviatnenko spotted another opportunity, joining Headway’s team to bring in a range of entrepreneurs, board members, and leaders who could connect with Anton and offer insight into the challenges and prizes that lie ahead.

“Headway Inc is already at a high caliber stage,” says Carlota. “So the best way Endeavor can support is by helping them raise smart capital in a smart way. You might have interest from three different investors, but who is actually the best partner for you? The question shouldn’t be how to raise $100M, but how to find the partner who will help you grow and be ambitious in the right way. Reverse due diligence is key.” That partner has now been found: Headway Inc announced that they had just raised a new round with Bullhound Capital, which will be used to accelerate product development, expand internationally, and strengthen its knowledge-driven ecosystem.

Anton’s drive to succeed is not just an individual passion, but a determination to prove that a massive public tech company can be built out of Ukraine. In his dedication to both his customers and his team, Anton has already broken perceptions about what can be achieved in business during war.

And if this is how Anton and his team perform during what Sviatoslav Sviatnenko calls the “new business as usual,” well… look out for incredible things from Headway Inc, and all of Ukraine, in peacetime.