LOCATION: Amsterdam, Netherlands
LANGUAGES SPOKEN: Bulgarian, English and German
CURRENT ROLE: CEO, WeTransfer
PREVIOUS LEADERSHIP ROLES:
Chief Product and Technology Officer, WeTransfer
CEO, Joyn GmbH
Product Management, Google
BOARDWAVE ROLES: Mentor
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. “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,” says WeTransfer’s CEO Alexandar Vassilev. “And it’s not going away. If anything, WeTransfer has become more and more important the more we rely on the Internet to do business. Files are getting bigger and the need to share information online is greater. And WeTransfer plays a critical role in that.”
Vassilev became the firm’s CEO in May 2022, and he steered the company to a significant milestone just eight months later: it reached half a million paid subscribers across both its premium and pro services in January 2023.
Vassilev has one eye on the future – he’s always searching for the next big problem that people need to solve. That includes looking at disruptive technologies, from blockchain through to AI, which can play a role in serving the creative workflow. “We are trying to think of what else we can help people with. We keep our eyes very focused on how the creative world is developing, because that’s kind of our bread and butter,” says Vassilev. “We are humbled by the fact that we are now one of those tech companies with an Oscar,” he says, proudly. He is referring to the Academy Award that WeTransfer’s digital arts platform, WePresent, won in 2022 for commissioning and distributing The Long Goodbye, a short film co-written by Aneil Karia and Riz Ahmed.
A creative arm doesn’t seem like an obvious fit for a firm focused on file transfers, but it stems back to how the company was conceived. “Our founders observed that every time they worked with a client, you would download a file on a USB stick and put it on a bike courier to drive to the client, and so they created WeTransfer,” he says. “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.”
Uniting ideas
Vassilev was born and raised in Bulgaria and, for the firstfive years of his life, he 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. As soon as communism fell, his father embraced entrepreneurship and started a business. This remains a hugely formative moment for Vassilev. “He had no role models, no literature, and he had to figure out everything on his own. His relentlessness in his own determination to get things doneand to do things the right way rubbed offon me. That’s how I define success.”
His father not only took a huge risk instarting a business, he says, but it alsokick-started Vassilev’s interest in tech.He vividly recalls his father bringinghome one of the early brick-sizedmobile phones. “He would sit down,disassemble it and put it back together,”he says. His father’s fascination withpeering under the bonnet of technologyinspired Vassilev: he taught himself tocode and build websites, launching hisfirst company as a teenager. Eventually, he decided to study engineering at Missouri Southern State University, packing his bags and moving to a city called Joplin.
Vassilev’s early transatlantic move set him up for an international life, and he has held roles in the US (at tech giant Google) and Europe. Because of this, he has learned – and benefitted from – the differences between how the two continents do business. “I think the capacity to think that you can do the impossible is something that rubbed off on me from my US days,” he says. “That freedom to try and fail 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.”
Vassilev acknowledges that being at Google when it was going through phenomenal growth was a huge privilege – but there was another side to Silicon Valley that he experienced. “We’ve seen what uncontrolled ambition can do, and we’ve seen some
companies do great things and some do bad things,” he says. In recent years, there has been backlash against Silicon Valley’s common “move fast and break things” philosophy from governments, regulators and consumers alike. It was a lesson Vassilev learned early on.
While at Google, he realised that ambition has to be tempered with humility. “I was young, very passionate and thinking about my next promotion. My boss said, ‘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.”
Vassilev has lived in rural and urban America, and moved around Europe – including Switzerland, Germany and, to his current home, Amsterdam where WeTransfer is headquartered. He is determined to use a “cross-pollination” of ideas that he has seen on both sides of the Atlantic and meld them together. “If you marry US ambition and creativity, and input the structures that exist in Europe and take a slower path, that’s a great recipe for success.”
Breaking the culture cycle
One of the topics Boardwave is most committed to is addressing the need for more diversity in the tech industry. Vassilev 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. 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, Vassilev 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. “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 response to queries. He said that learning how different cultures respond to tech was humbling. “I’ve taken that with me my whole career,” he says. “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,” Vassilev says.
That search for knowledge is perhaps why Vassilev left the tech giant 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 see the world outside,” he says. “I didn’t want to end up in an environment where I know one thing for many years.” He decided to study further – 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.
Journey to the continent
Vassilev describes the MBA as transformational – it was an opportunity to meet people from different industries and be exposed to new ideas. But, after completing it, he ended up 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 ended not by business ambition, but when real life intervened. “I happened to fall in love with someone and that someone was in Europe. It facilitated the change and I resigned for the second time.”
As well as embarking on a new personal life, he took on a fresh business challenge building a streaming platform with a start-up called Joyn in Germany. Armed with his knowledge from Google, he was determined to craft something with a strong culture and vision. “I had the audacity to try to create things, but in a structured way,” he says. “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 Joyn in 2020, the firm had a 10% share of the streaming market – not bad when you factor in the established firms it was competing against.
For his next venture, Vassilev joined WeTransfer as Chief Product and Technology Officer in 2020. “I was really interested in taking the next step, which was scaling up a bigger business,” he says. “The plan was to understand the business, help it scale, and strengthen the product development as much as I could.”
What advice has most inspired him through his international business journey? Surprisingly it came 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 says. “He was so selfless and would do everything he could for his employees. He would stay late and sacrifice his family time so that we wouldn’t have to. Leading by example and putting yourself last, that stuck with me.”
The memory of a boss sacrificing their family time strikes home now that Vassilev is a parent himself. “I’ve dreamed of being a father for many years. Of course, it comes with a lot of challenges but it also gives me perspective.” He is laser- focused on how he uses his time, so that he can continueto grow WeTransfer and be around to enjoy family life too.
Tips From The Top
What are your tips for a successful business?
1. 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.
2. 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. You should stay focused on the communities you’re serving and their daily realities.
3. Expect the unexpected. 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.
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.
Can you tell us something surprisingabout yourself?
I’m a chess enthusiast – albeit a mediocre player. I’m fascinated by how the combination of a single board and two brains can lead to 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.
Is there a piece of tech, other than your phone, that you could not live without?
A dishwasher. I love technology that solves real-world problems – but also I am an eager but messy cook. It is also a reflection of my childhood in communist Bulgaria, where there was a lack of consumer goods.
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