bove Amsterdam’s cobbled canal paths, the deal team for WeTransfer assembled to ring in 2015 in style. But this wasn’t just any old New Year’s Eve celebration. As the clock crept towards midnight, Highland Europe was putting the final touches to its investment agreement with the Dutch start-up.

“It was approaching 8pm and while most people were at home with their families, we were in a dark tower, finalising bits with the lawyers,” recalls WeTransfer’s co-founder, Bas Beerens. “But none of us minded that it was New Year’s Eve. We just wanted to get the job done.”

While there’s rarely an investment deal that closes without the acoustic backdrop of champagne corks popping, the toasts that night were particularly special. It was both the dawn of both a brand new year and of a progressive new chapter in WeTransfer’s history. It also marked the end of months of intense work. Highland partner Tony Zappalà says that even though that night was officially only just the beginning, it already felt like WeTransfer and Highland had been partners for years.

Bas agrees that the deal had been a long time in the making. He had spent 2014 evaluating a slew of strategic options, speaking to banks, investors and potential acquirers, but Highland had distinguished itself by offering a truly “human connection”, he says.

Highland partner Irena Goldenberg, says that she immediately recognised the extent to which WeTransfer and her own company mirrored each other in their passion for putting people at the forefront of business. And she was particularly taken with their quest for new creative individuals to enhance the brand’s creative essence. Even Lady Gaga’s talent manager, Troy Carter, was thrown in the mix via one of Irena’s connections and ended up joining the board of the company.

One of the greatest challenges of expanding a company successfully is ensuring that leadership is always structured in the most effective way. Bas reflects on an important meeting in Geneva during which Tony suggested that he – a creative, product guy at heart – step back into an Executive Chairman role, handing the reins of day-today operations to a new CEO.

“The idea initially conjured images of a big leather chair and cigar and at first I was offended,” Bas explains, “but towards the end of the meeting, I felt quite relaxed.” Within a week Bas had agreed with Tony that it was the right move.

Tony took on the interim role of CEO while the search for a permanent replacement got underway. Bas says that Tony taking over temporarily “served as a rehearsal for letting the baby loose and it worked really well.”

In late 2016, WeTransfer crossed paths with Gordon Willoughby, formerly of Amazon and eBay, and the latter immediately recognised a unique opportunity. “My initial interviews took place at a restaurant called Happyhappyjoyjoy, as opposed to a meeting room named 1G, and I realised then I was in for a very different experience!”

As an investor, Gordon describes Highland as “concerned but not controlling,” which was perhaps unusually exemplified during Gordon’s early days in the job when, during a visit to WeTransfer’s Amsterdam office he paced face-first into a glass door. His face required stitches and his ego was certainly bruised, but he recalls that, ever the professional, “Tony didn’t say a thing but the next time I was in Amsterdam, there were these white seagull stickers on the glass door – just about head-height.”

In investing as in life, sometimes it’s the subtle gestures that really matter the most.