As part of our Tales in Tech series we’ve been catching up with members of our tech community to share the journeys, lessons learnt and advice that has helped them through their careers to date.

Established CTO Dave Cook, also known as The Yorkshire Cowboy, has been leading businesses through digital transformations for over two decades. Dave lives by the philosophy of ‘lifelong learning’ and is now giving back to the next generation of CTOs by providing resources and guidebooks for professionals wanting to progress along a similar pathway. In his most recent challenge, Dave took on joining a start-up and is currently CTO of Havn Super App. We sat down with him to talk about scaling and downsizing teams, life before leadership roles and why he believes life-long learning is fundamental to a successful career.

Tell us a bit about yourself and your role as a CTO:

I’ve been in the tech business for over 30 years now and I have the pleasure of living in Yorkshire. I have two passions in life, one is my horses and the other is lifelong learning, which sounds very dull when you say it like that! I’m currently CTO at a start-up called Havn, which is quite an interesting arrangement given lockdown. We’ve got Developers based all over the world from Indonesia to Mexico, so it’s been quite a challenge running an agile team across that breadth of geography and time zones.

I’ve had C-Level roles at 5 other companies, all different sizes. From scale-ups, PLCs, LTDs, and Private Equity owned, so I’ve got quite a wide experience of different organisations.

How has it been leading and managing everyone whilst everyone is remote? Did it take some getting used to?

We were already used to a certain amount of remote working, but the biggest observation I’ve had is our ability to collaborate just as well virtually as we would in real-life.

I’m building an app with one company in Poland at the moment and typically when you kick off a project like that, you’d all be together in a room and we’d have done this great big workshop. We did everything over Google Meet and used software for the whiteboarding and it worked really well. Everything was done across two days and we didn’t have to spend any time or money on travelling. So, it’s been a real revelation that you don’t need to travel to be productive.

Tell us a bit about your life before leadership and the roles and projects you were working on?

I studied Astrophysics at university and started out as a Software Engineer working at the European Space Agency. That was pretty cool, but I didn’t make a lot of money and there wasn’t a lot of career progression. My first Management role gave me the realisation that I had a skill that I could leverage, so I went on to become a Management Consultant.

My first chance at a C-Level role was with a hedge fund in the city, where we spent three years re-architecting their whole platform so they could scale. They grew over 7x during that period and we scaled up from 15 to about 120 people in technology spread around the world, so that was a pretty big project!

After the crash of 2008 I went on to Autotrader to run the technology team during what we called the ‘print-to-digital transformation’. Autotrader used to be this great magazine from the 70s advertising used cars, but it had to move online to keep up with the times. I worked there until the project was complete and the last magazine came off the shelf. Since then I’ve done various digital transformation projects and recently decided I wanted to join a start-up to see what that was like. So, you know, I’ve mixed it up!

In the early stages did you miss the coding and technical side of things or did you enjoy the people management side?

I’m not naturally a people person but I realised that you can get more done by leading other people. You can only work so many hours a day and it doesn’t matter how good you are, you can only produce so much. If you’ve got the ability to build and lead a team you can get much more done, so your value increases - and if your value increases so does your pay.

Having worked across a range of businesses from start-ups to hedge funds, do you think you have a preference, or do you like the fact you’ve had the opportunity to dabble in all of them?

I like the fact I’ve dabbled. The preference is definitely organisations that are growing and are on a mission. That’s where you get the right energy. I think that’s why start-ups are so interesting. They don’t have any of that legacy, they’re just trying to grow and come up with the next big idea.

What are some of the biggest challenges that you’ve faced as a CTO?

Probably downsizing. When you’ve spent time building a team and you know everyone and their families and individual situations. It’s very hard having to professionally approach that conversation with people. Downsizing and making people redundant is just awful.

What do you think is the most important thing you’ve learnt when it comes to scaling and building a team?

The tech team needs to understand the business. If you don’t understand why you’re there and what it is that keeps the business running, then you’re missing out on an awful lot and not adding the value that you could be. As people join the team it’s important to educate them. You need to get them to really understand what value they’re bringing and bring them in on the mission.

I also think trying to be as open as possible with people. People aren’t stupid, they know what’s going on. As Managers we can often be quite secretive about things and what we share, and I think that’s detrimental. Having a culture where you can be open with people is really important.

What do you think are the three skills that are most essential in your role?

Strategy is a key one. It’s often the first question we get asked as a CTO. You get a few days grace and then it’s like – so what are we going to do? We need to come up with that plan.

I’d then link that with creativity. There are always going to be opportunities or obstacles and you need to be able to contribute to creating something new or solving a problem in some way.

The third one I’d go with is keep learning. If I hadn’t had twigged way back when that learning was an important way to spend some of my time, then I wouldn’t have got to where I am.

Learning is never urgent, so we tend to delay it and forget how important it is for our long-term career. The skills you have today aren’t the skills you’re going to need tomorrow. With the world constantly changing and technology often being at the heart of those changes, you just can’t rest, you’ve got to keep developing.

Is that what led you into starting your blog and training courses?

Yes, I’ve been helping to develop people since I became a Manager. I turned 50 three years ago and thought, what’s my legacy? What am I going to give back to the world? I documented the methodology that I’ve used for all these years and I called it, ‘No limits to learning’.

More recently people have been asking about the journey I took to become a CTO. So, I spent some time being creative, thinking about learning and building a strategy to create my course, ‘How to become a CTO’. I wanted to give something back to the next generation of technology leaders and those who want to progress in their careers. There aren’t many places you can go for a guidebook – so I thought I would put one together and see if people like it!

What advice would you give to someone striving to take a similar career path?

Add value every day. As a Consultant you think to yourself, I’m costing you a lot of money here, what have I achieved today to be valuable? And if you can’t answer that question then you probably shouldn’t come back tomorrow!

Realise that you are part of the business. Really understand the business that you’re in and why technology is so important for that business in achieving their results.

And finally, keep learning!


A huge thank you to Dave for taking the time out to talk about his journey to CTO and for sharing his experiences and advice. If you would like to find out more about The Yorkshire Cowboy and his learning resources, you can find all of the information here.