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Hello! What's your background and what do you do?

I’m the Co-founder and CEO of EmailOctopus, an affordable email marketing platform. We’ve been in business since 2014 and are mostly aimed at startups, small businesses and entrepreneurs. Our USP is that we’re around five times cheaper than other solutions out there.

Programming has always been a passion of mine, and I started it as a hobby when I was around ten. That led me to start creating websites and then my first business when I was fourteen. I studied Software Engineering at university and had a couple of programming roles after that; first at the Royal Opera House in London, then as Head of Digital at a startup news agency focused on cryptocurrency reporting.

I set up EmailOctopus five years ago with my brother Gareth, who’s a marketer, and I maintained the business alongside my full-time work. Two years ago it finally got to the point where I could quit my day job and focus fully on running my own business. It’s been a huge learning curve — not just moving away from development and into management, but learning everything else I didn’t know about being solely responsible for keeping a business afloat.

The company is based in the UK but my wife and I decided to move to Vancouver last summer and I’ve been working remotely from here ever since. Taking that decision is obviously a huge benefit of what I do, but being remote adds new challenges to managing the team back home.

How was your transition from software development to management like?

The transition has been fun, messy, difficult and it certainly isn’t over yet. EmailOctopus has continued to grow steadily over the past two years — we’ve now had 30,000 customers send five billion emails through the platform. We’re still a small team of five, so I wear many hats alongside being a manager and leader. I still get drawn into development and there’s constant technical firefighting as the platform grows. At the moment my number one priority is building a strong roster of contractors so I can step away from the day-to-day engineering and focus more on management and the future of the company.

In terms of learning to lead, I’ve been doing this on my own so have had to pick things up along the way, and I’ve missed out on having a strong manager myself to learn from. When I first went full-time on EmailOctopus, my brother and I hired Tom, our COO, to pick up a lot of the business operations, and he was integral to getting things up and running while I focussed on the technical side. Now that we’re bigger, I’m pushing myself to focus more on leadership and strategic direction.

What does your day-to-day work look like, and what motivates you to do it every day?

The first two hours of my working day are the most important: that’s when our working hours overlap and I get to talk to the team in the UK. We have a handover call where everyone discusses what they’ve done that day, then each week I’ll have 1:1 conversations with all members of the team. This generally happens at my kitchen table, then I take the bus downtown where I have a desk in a coworking space.

In terms of my day-to-day tasks, things are pretty varied. I’ll spend around 40% of the day programming and reviewing code, then the rest of the time is meeting with the team, scoping upcoming projects, working with contractors, managing the finances, reviewing our marketing… It’s both rewarding and stressful being involved in so many different things. My favourite part of the day is sitting down to review what the UK team has produced — it’s awesome to see how much has been created while I’ve been asleep.

Seeing our product grow is my number one motivation and reward. People really do value our platform and we’re helping them grow their businesses in turn, so it’s great to hear positive feedback from customers.

What are the biggest challenges you've faced so far? What did you do to overcome them?

My biggest personal challenge is tearing myself away from programming and thinking of myself as a manager first, developer second. I’m doing that more now but I should have done it sooner. I still have a tendency to get sidetracked and become absorbed by a small technical task — for example, this morning I spent way too long on the design of a checkbox. If I don’t watch myself, this sort of thing becomes a way to procrastinate and put off management tasks like making business decisions. Programming will always be where I feel most comfortable, but ultimately I’m rewarded by seeing the company grow — and it can’t do that while I’m just programming.

We’ve also just recruited another full-time member of the team in the UK recently, and I’ve realised how much harder it is to build that relationship and welcome someone when you can’t spend time face-to-face. I take for granted how easily I work remotely with the older team members because I know them so well, but with new people it takes longer when you can’t chat about a problem or go for a beer after work. I’m conscious of that and I try to travel back to the UK every few months so I still feel connected. And the benefit of being remote is that you have to try harder to be clear in your communication, and organised about documenting everything, so I think it makes us a stronger team overall.

What has been the biggest surprise so far? Something you didn't expect?

To be honest, I never thought I’d enjoy managing a team. I’ve always been motivated by making and building things, and when I worked in other organisations I didn’t want my managers’ jobs. But it turns out I really do love it, and I find it so rewarding to see my team’s good work, especially when they’ve done something great that I never would have thought to do. It sounds cheesy but I now know that we can build much better, more exciting products working as a team rather than me going it alone.

What's the best advice you've received about being a manager?

I read this somewhere online recently and wish I could remember the source, but I can’t. The gist was that half of being a manager is managing other people, and half is managing your own behaviours. That’s something I always try to keep in mind: am I being a good role model? Am I being clear? Am I reliable?

What do you tell developers who are considering making the switch or new to the role?

I tell them that the reward and satisfaction you get from your job will inevitably change. Programming is so instantly gratifying: build something, launch it, find a problem, fix it. There’s a steady drip feed of validation all throughout your day which feels great and is pretty addictive. But once you move up into a management role, a lot of that goes away and the reward you do get is secondhand — it’s seeing someone else’s success and sharing it with them. And your end goal is rarely clear, there’s not someone else defining the scope of your work. It’s up to you to decide what’s next for the team and then get everyone on board.

With that in mind, moving into management definitely isn’t going to be a great option for all developers. So think about it fully and decide whether you’re willing to let go of what you enjoy about coding.

Final call to action! Where can we go to learn more about you?

Check out EmailOctopus or find me on Twitter.

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