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Alexandar Vassilev: CEO, WeTransfer

WeTransfer CEO Alexandar Vassilev on humble ambitions, the cross-pollination of US and European culture, and why his dishwasher is the piece of technology he can’t live without. WeTransfer has built a loyal following, winning fans because of its simplicity of purpose – it solves the problem of moving large files around the internet, and it solves it well.

When I tell CEO Alexandar Vassilev that I personally use it all the time and love it, he smiles. I suspect he gets that kind of praise of a lot. “A lot of companies say that they are solving problems but, for us, it really is at the heart of what we do. I’m not a fan of slogans or mantras but we are focused on making sure we solve this problem. And it’s not going away. If anything, it’s becoming more and more important given the fact that everything is moving to the digital space. Files are getting bigger and the need to share information online is getting bigger, and WeTransfer plays a critical role in that.”

That’s not to say the company is complacent. Alexandar became CEO of WeTransfer in May 2022, and in February clocked up a significant milestone – reaching half a million paid subscribers across both its Premium and Pro services.

But he always has one eye to the future, looking for the next big problem that people might need to solve. That includes looking at new and disruptive technologies, from blockchain through to AI, which can play a role in serving the creative workflow. “We are trying to think of options of what else we can help people with. And we keep our eyes very focused on how the creative world is developing, because that’s kind of our bread and butter,” explains Alex.

“We are humbled by the fact we are now one of those tech companies that has an Oscar.” he adds proudly. He is referring to the fact that WeTransfer’s digital arts platform, WePresent, won an Academy Award for Best Live ActionShort Film in 2022 by commissioning and distributing The Long Goodbye, directed and co-written by Aneil Karia and Riz Ahmed.

And when I highlight that a creative arm doesn’t seem like an obvious fit for a firm focused on file transfers, he reminds me of how the company was conceived.

“Our founders observed that every single time they worked with a client, you download a file on a USB stick and put it on a bike courier to drive it to the client, and so they created WeTransfer."

“This connection between who we are in our DNA and the creative world, we never lost that, so it was the most natural thing for us to have a creative arm.”

Alexandar began his career as an engineer, so simplicity of design is close to his heart. I ask him what piece of technology, other than his phone, he couldn’t live without and his answer seems surprising at first – a dishwasher. The choice isn’t just a nod to his love of technology that solves real-world problems, or a reference to the fact that he is now an “enthusiastic, if messy” cook, but also a reflection on a childhood lived without consumer goods.

Alexandar was born and raised in Bulgaria, and for the first five years of his life lived under the communist regime. His memories of that time reflect the politics he was growing up with – standing in line for basic necessities and living in a small apartment with a lack of consumer goods (including not having a dishwasher). As soon as communism fell, his father embraced entrepreneurism and created a business, and this remains a hugely formative moment for Alex.

“He had no role models, no literature, and had to figure out everything on his own.His relentlessness in his own determination to get things done and to do things the right way, that rubbed off on me. That’s how I define success.”

His dad not only took “a huge risk in starting a business,” but also kickstarted Alex’s love for tech. He vividly recalls him bringing home one of the early-adopter ‘size-of-a-brick’ mobile phones. “He would sit down and disassemble it and put it back together,” he tells me. That fascination with peering under the bonnet of technology also rubbed off on Alex, and he taught himself to code and build websites, launching his first company as a teenager.

But another, more international life was calling and, aged 18, he packed his suitcases and left his family for the not-so- bright lights of the USA’s Midwest, a town called Joplin, where he attended Missouri Southern State University, studying engineering.

As someone who has not only moved from Europe to the US and back, and from one of the tech world’s biggest firms, Google, to a German start-up,I ask what he has observed as the biggest differences about the way business is done on the different sides of the pond.

“I think that capacity to think that you can do the impossible is something that rubbed off on me back from my US days,” he tells me. “That freedom to try and fail. That freedom is not something we’ve championed for a long time in Europe. It’s something that’s relatively new in the way we do things.”

And while he acknowledges that being at Google, when it was going through phenomenal growth and was the company where everyone wanted to be, was a huge privilege, there was another side to Silicon Valley. “We’ve seen what uncontrolled ambition can do, and we’ve seen some companies do great things and some companies do bad things,” he says.

In recent years, there has been some backlash against the ‘move fast and break things’ philosophy many Silicon Valley firms were built on from governments, regulators and consumers alike, but it was a lesson Alex learned early on. While at Google, he realised that ambition has to be tempered with humility. “I was young and very passionate and thinking about my next promotion. A boss said that everyone was obsessed with what is next, but -

"If you want to make it, you have to be good at what you do now. It sounds so simple but it’s become my mindset – prove that you are doing a really good job here before you move on, so not ambition for the sake of ambition.”

Having lived in both rural and urban America, and moved around Europe – Switzerland, Germany and to his current home in Amsterdam, where WeTransfer is headquartered - he is also determined to take what he calls the “cross- pollination” of ideas he has seen on both sides of the Atlantic and meld them together.

“If you marry some of the US ambition and creativity, and input some of the structures that exist in Europe and take perhaps a bit of a slower path, I think that’s a great recipe for success,” he tells me.

One of the topics Boardwave is most committed to is addressing the need for more diversity in the tech industry, and, as a male CEO, Alex is proud that WeTransfer has a high number of women at senior level, including Martha Lane-Fox who heads up its supervisory board.

But, he says, it isn’t just the gender gap that firms need to think about. He witnessed for himself how a lack of diverse thought can hamper product design. “Google built a lot of products for the US market. And you expected that this type of usage behaviour, these types of needs are going to be the same that you encounter in, say, the Indian market.”

But in a project looking at how Google was used in India, Alex and his team discovered that consumers were more likely to search on Facebook than Google. “It seemed strange. Why would you search on a social network versus Google, a search engine? And we found that people were intimidated. They came to Google and they just saw a bar in an empty page. “While in the US this was the best possible experience – no colour, simplicity, just go and ask your question – for someone who has never experienced Google from another part of the world, asking the question is actually the most difficult thing. Because what is the question? What can I ask?”

By contrast, he explained, many found Facebook a less intimidating place to ask questions because it was where their friends and connections were, offering a gentler kind of response to queries. He said that learning how different cultures respond to tech was “Humbling - I’ve taken that with me my whole career. I think you have to keep pushing and challenging yourself to do better in order to build not only inclusive businesses, but products that work for everyone, not for the select few you happened to look at when you built it.”

That search for more knowledge is perhaps why he left Google in 2014. “All I knew was Google. All I knew was how Google worked. All I knew were the people at Google. So it was very difficult for me to kind of see the world outside. And I didn’t want to end up in an environment where I know only one thing for many, many, many years.”

He decided to go back to study – this time for an MBA. He admits there was another reason behind the decision. “I had a chip on my shoulder from my entrepreneurship days where I realised that technology is not enough to build something that’s successful.”

He is referring to the start-up he began in Bulgaria as a teenager, which ultimately failed.

He describes the MBA as “transformational,” an opportunity to meet people from different industries and be exposed to new ideas.

So it’s somewhat ironic that after completing the MBA, he ended up working back at Google. “It wasn’t planned. I was looking at different options. But a former manager of mine who I respect incredibly called me and I couldn’t say no.”

A short stint back in California, on an interesting project to improve Google’s search offering, was ended not by business ambition, but when real life intervened. “I happened to fall in love with someone and that someone was in Europe. And that kind of facilitated the change, and I resigned for the second time.”

As well as embarking on a new personal life, he took on a new business challenge – building a start-up in Germany, a streaming platform called Joyn. He did so armed with his knowledge from Google and determined to build something with a strong culture and a strong vision.

“And of course, the audacity to try to create things, but in a structured way,” he adds.

“It was building a business and a product from the ground up and having to prove yourself in the context of a small company. We ended up building that business to about 300 people.”

By the time he left, the firm had a 10% share of the streaming market – not bad when considering the behemoths such as Netflix it was competing against. He joined WeTransfer first as Chief Product and Technology Officer. “I was really interested in taking the next step, which was scaling up a bigger business,” he explains. “The plan for me was to understand the business, help the business scale and strengthen the product development as much as I could.”

So what advice has most inspired him through his international business journey? Like the dishwasher, the answer surprises me because it comes not from a Google executive or a business partner, but from the director of IT Services at the University he attended, where he worked part-time as a student. “Jeff was the kind of person who would jump through fire for you. And so, we were willing to jump through fire for him. It was about loyalty. He was so selfless and would do everything he could for his employees. He would stay late and sacrifice his family time so we wouldn’t have to. And it was this kind of leading by example and putting yourself last that stuck with me.”

That memory of a boss prepared to sacrifice family time likely strikes home now, as Alex embraces yet another new challenge - fatherhood. At the start of the interview, he warns me that his six-month-old daughter might start crying during our chat, so I ask him how he is finding being a new parent. “I’ll tell you a secret. I’ve been dreaming about being a father for many, many years. I’m happy that I am one. Of course, it comes with a lot of challenges, but it’s been a monumental moment for us and personally, for me, it gives me perspective.”

That perspective means he is now “laser-focused” about how he uses his time, so that he can continue to grow WeTransfer and be around to enjoy family life too.


Tips From The Top

What are your three tips for a successful business?

Solve real-world problems – The phrase ‘product-market’ fit is often touted as the holy grail. But it’s more than that: it’s about actively going beyond market estimations and focusing new innovations on actual behaviour and real problems that people, businesses or societies have.

Stay focused – The world of fast-growth tech is very competitive, and it’s easy to get caught up in one-upmanship, especially as businesses scale and fight for attention. Atthe end of the day, you should stay laser-focused on the communities you’re serving and their daily realities.

Expect the unexpected – This barely needs to be explained but I believe that coping with globally disruptive moments is the new norm. It’s about how businesses roll with the punches and grow into the ebb and flow.

Tell me something surprising about you?

I’m a mediocre chess enthusiast. I’m fascinated by howthe combination of a single board and two brains can leadto endless positions, all completely unique. Whoever your opponent, it comes down to logic, creativity within the constraints of the board and doing more with less. It’s a beautiful game.

How do you relax?

It sounds boring but I read. With my life and work so centred on digital, picking up a physical book is timeless. Science fiction is my go-to for switching off and getting lost in new worlds and realms.


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