Name: James Crowley
Age: 33
Current position: Co-founder and CTO at FundApps.

My career summary — multiple attempts combining technology and business! At FundApps I’m leading the technology and product team as we simplify regulatory compliance for the investment industry — our service analyses $3+ trillion in assets daily, and is used by some of the largest financial institutions across the world. I’m also co-founder of SDD with conferences and deep dive training in London featuring industry-leading speakers.

I love the outdoors, particularly mountains and water, so give me any excuse and I’ll be there.

Tell us about your life before leadership — what kind of roles and projects did you work on?
I started learning to code while studying for my GCSEs in the late 90s, publishing tutorials online as I learnt. These were the days you could make money out of advertising to a comparatively niche audience, so I accidentally ended up with a small business too. Sitting in my bedroom, interacting with people all around the world, and making some money too? Well, it beat a paper round!

As Developer Fusion grew — ultimately reaching 600,000 unique visitors a month — I was lucky enough to meet some great people and opportunities arose from that. I had a pretty varied mix of online publishing, advertising platforms, ecommerce and other b2c websites and creating some commercial software components. What really stuck with me though, was the freedom and satisfaction that came from building a company and using technology to do it.

How did your first leadership position come about, and was it intentional on your part?
My first permanent job after university was as ‘Head of Development’ at a digital agency spin-off. I started with zero team members and a lot of coding to do, and we expanded the team from there as the business grew. It wasn’t intentional as such, just seemed like a good opportunity and I liked the people!

How did you manage the transition? What came easily / what was difficult?
The transition was gradual, so the responsibilities slowly crept up on me! At the start, I was in my comfort zone — working with customers, setting up technical best practices like testing & automated deployments (seemingly rare at digital agencies back then), and doing some of the coding too.

Combining my technical knowledge with the business comes pretty naturally to me but I have a strong tendency to focus on technology rather than people — so that was the big challenge as the team started to grow.

What was your biggest failure in that first leadership role?
In hindsight, probably not realising that I was even in a leadership role. I didn’t think too much about it — was just ‘in’ it and getting on. I was largely oblivious to what I’m sure were many failures at the time!

At FundApps the role has evolved over time too — from purely technical, to managing the team, to finding an engineering manager and switching back to a more technology and strategic focus. This time I’ve been more conscious of my responsibilities as such, but just as you might be vaguely approaching a comfort zone, it all changes up again!

What made you keep doing it?
I’m a sucker for a challenge provided I’m learning a lot while pulling my hair out!

Tell us a fun fact that nobody knows about you
I stumbled across an old video the other day, of a tandem bungee jump with a friend many years ago. I have no shame in saying I screamed my head off. I got butterflies in my stomach just re-watching the moment of jumping off that ledge!

What are the three key skills you think every lead needs?

  • Genuine interest in figuring out how to help your team members excel and grow
  • Self-awareness of your own strengths and limitations particularly with regards to both technology and people, and adapting accordingly.
  • Willingness to address issues head on and have honest and sometimes challenging conversations. I tend to avoid conflict at all costs, so this is one that I have to work on a lot.

What have you learned about acquiring and retaining talent?
There are so many aspects to this!

  • Finding the right people, at the right time is, strangely enough, hard work! Out of the talented folks at FundApps we have someone originating from every possible source — family (!), personal referral, direct applicants, job ads, contact after we found their profile, recruitment events, in house and external recruiters and hiring platforms.
  • Ensuring the interview process is structured and repeatable so we can fairly evaluate candidates, without being robotic and unthinking. The closer you can get to the simulating the real work, the better — reviewing & writing code with a peer, as a prime example.
  • Any good candidate is going to be evaluating you too. If you’ve got a work
    environment and team you can be proud of, then this bit is comparatively easy — just make sure the recruitment process is honest and open enough that potential candidates get a real feel of the culture.
  • Once you’ve got the talent on the team, give them the trust, freedom & support to do their best and keep learning.

How do you motivate your team and manage their stress levels?
At the very least I try to ensure I am removing stress not adding to it, and ensuring we take the time to fix and remove self-inflicted causes of stress in our own technology.

I strive to ensure the team has autonomy, with clear boundaries and objectives to steer them, to know they have my trust — and can talk to me whenever they need. I try and set high standards, while recognising when the team or individuals have gone the extra mile. I fail at all of this frequently, but it helps to know what you’re aiming for!

How do you manage your own stress levels and productivity?
I’m lucky enough to work 4 days a week, but even then, I regularly struggle with managing stress and energy levels.

Working as a co-founder and CTO means the role comes with an awful lot of freedom (thanks to my long-suffering co-founder CEO!) — but equally a great feeling of responsibility. You never stop asking yourself — am I working on the right things for the business and the team? The right things to keep myself motivated? What am I not thinking about that I should be?

I truly switch off by focusing on something I enjoy learning and am rubbish at, of which there is an endless list — surfing, ice skating or drumming to name a few — while trying not to overdo it either.

In terms of productivity — a lot is said about how our psychology is being exploited by the devices and services that in theory we use for our benefit. I try to address the basics – no notifications on my phone, and don’t take it to bed — with mixed success so far!

How do you stay in sync with other parts of the business?
This was almost effortless in the early stages of FundApps, when everyone was co-located in London. As more people have joined the team and we’ve become geographically diverse (New York, Toronto, Sunderland & soon Auckland), it’s become exponentially harder to maintain the same level of context and awareness.

I had to accept that I could no longer know every single business opportunity, customer request or review every line of code! Instead, I have been (slowly) figuring out the level of detail that is worth maintaining — and trying to set expectations so the right things come to my attention if they are going off track.

Where do you see yourself in 5 years’ time?

I’ve had to reinvent my role and own goals several times on the journey so far, so I am still figuring that one out!

What product do you wish you’d invented?

The bicycle! You can travel the globe*, or just head around the corner, use it for work or pleasure, enjoy it on your own or with friends, and all with a low impact on the world!

(*admittedly with some effort…)