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How to go from freelancer to CTO

Frank van Rest started his career in IT getting rid of viruses on laptops in the 90s. The next decade he developed his skills as a web developer, leading up to his CTO position at Learnbeat throughout most of the tens. Today, he’s the co-founder and CTO of RunFriendly, re-thinking urban mobility in major cities across the globe.


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“Not too long ago, I was responsible for the technical side of a fast-growing scaleup, preparing to take the next step. Obviously, there was a lot to consider, but what fascinated me most was how diversified my skill set had become after growing with the company in the last eight years. Many companies have different people for a variety of roles, be they CTO, software architect, product owner, and team lead. At Learnbeat, I did it all.” So, for what it’s worth – and for all the software developers out there aspiring to become founders – here’s what Van Rest learned along the way.

Do what you love

When Learnbeat founder Koen Strous asked Van Rest to join in 2012, it wasn’t a difficult decision. The two had been working together on a contract basis for a year and half. Ever since Strous reached out to Van Rest, after one of Van Rest’s apps received national media coverage in 2010.

“I went from creating websites for law firms to building multi language platforms for international brands like Mentos. But I was still selling my time, and I wanted to do something bigger and better than what I could do by myself. Today I know a lot more about what I want, but 10 years ago, it seemed like a safe bet to work with someone I knew and on a product I had positive feelings about. Instead of working for some random big tech company or as a freelancer.”

“The biggest difference between being a freelancer, and running your own business,” Van Rest recalls, ”is that as a freelancer, you get tossed away when a marketing campaign ends. When you’re the owner, you’ll be confronted with last year’s code every single day. And it’s your code. You are responsible for improving your service over time. Even if, in our situation, that meant sitting in the back of the classroom. Watching how students were using the features I built. But you’ll also feel the excitement of your service growing along the way.”

“In addition to this,” Van Rest says, “is that you have to learn how to scale. And to love learning how to manage this. In the early days of Learnbeat, the service was hosted on the same server as the websites I built for Mentos. But because of our growth, and because educational platforms are common DDOS targets, our load increased so fast no Dutch party could handle our traffic and we switched hosting providers three times in a short time period.”

Work with people you like

A few months into Learnbeat, the founders struggled to find their first hires. Just like everywhere else, technical talent was hard to find. “When we opened applications for a marketing position, we received twenty responses, but for a position as software developer, none. So we tried hiring from our own network and through headhunters.”

“We quickly stopped hiring from headhunters due to the lack of qualified applicants and started looking for self starters. Recent graduates who already built stuff in their own free time. We prefered recent graduates because they understood what we were trying to achieve and because they knew about recent developments in our field. We prefered self starters, because being one showed true interest in the field. The only thing we had to worry about at that point was that they hadn’t worked in a professional environment yet.”

“Some overslept for an hour and a half, on several occasions. It actually made me laugh. Also, that they were not perfect was comforting for me, because I had never been a manager. And this way I could also learn that part of the job. Plus, I cared more about results than how they got there, so as long as the team accepted the responsibilities, there was no reason for panic.”

Take care of those around you

Consider the person

Early on, Van Rest and his co-founders realized they wouldn’t be able to hold on to their team competing with the big tech companies on the size of the paycheck, so, besides having a vision and repeating it, they needed to focus on secondary conditions to create a fun atmosphere.

“There was an endless list of possibilities for our employees to engage with the rest of the team. And for management to be something other than a manager for once,” Van Rest recalls. “We did so-called Thursday Talks, during which someone would give a presentation about something they loved. From meditation to being vulnerable. Everything was accepted, because through people’s passion, you really got to know them.”

“Then there were monthly bootcamps for our users. We invited them to a hotel in the city and showed them everything about the platform, while having fun with our team members. Going on boat tours, organizing table tennis competitions. Something magical happens when an intern beats the CTO in a competition.”

Long term this resulted in a special relationship, not only with its current employees, but also its former team members. “Every once in a while an ex-employee organizes drinks for all ex-employees. People from all over the country show up and recollect memories about what, for most, was an amazing first professional experience.”

Consider the professional

“I knew the CTO position would require more responsibility, but did that have to mean spending less and less time on our product? Yes, it turns out, and more.”

“You have to learn how to find the right people, guide them, give them perspective, especially young people, and train them. Enable inexperienced developers to contribute quickly to a product many benefit from. Developers chose to work with us, because we created a safe environment, in which even interns could launch new features.”

Van Rest spent much of his time at Learnbeat as a filter. “For developers, it can be difficult to manage all the requests from other teams. Especially when the requirements change every so often. Everyone needs their piece of the puzzle now, faster, bigger, better. It’s up to the CTO to not only balance the workload of their team, but more importantly, to make sure other teams realize what they’re asking and how it influences the rest of the organization. To have other teams consider your workflow, requires a level of transparency, that doesn’t always come easy. Especially when not everyone fits the same lunch table anymore.”

It was between 10 and 40 people that the co-founders added team leads, “team members who have the added responsibility of communicating between employees and the founders. As founders, it occasionally happens that you have to be fully focused on a customer or on investor demands for several days in a row. During that time, you don’t want your team to be bothered by your changing priorities, but you do want those who agreed to the responsibility to be aware of what’s happening.”

Again, consider the person

When you feel like all your time is spent on taking care of your team and providing them with everything they need, it can be painful, especially for first-time CTOs, when someone quits the company. “But soon enough you realize that people don’t stay with the same company for fifty years anymore and it will make you proud to see where they end up. You might have contributed, even if it’s just a little bit, to their professional development.”

“Being CTO means doing things that are bigger than little old you. Part of this means you have to accept the fact that you need to let go of team members when they feel it’s time to move on.”