From Technical Expert to Strategic Leader: Meet CTO Des Matthewman
Not only did he build, fund, and sell PORTABL.co, the world’s smartest platform that secures, empowers, and improves the wellness of independent workers, but he also serves as fractional CTO for companies looking to transform the future of work.
With massive insight, good humor, and a couple of violent agreements, this interview with Des might just be one of our favorites.
Interview by Sofia, Marketing Director at Cloud Employee
The Interview
Sofia: “Des, would you tell us a little bit about yourself? What’s your journey to CTO been like?”
Des:
I currently serve as a fractional CTO for four companies: Cloud Employee, Birchstone, Envelo Solutions, and Securus Software, which is a digital safeguarding software company in the UK education sector, where I've been for nearly six years.
Before my current roles, I spent 18 years with a single FinTech company (before we even called it FinTech!) through four acquisitions, ultimately being acquired by a FTSE 100 company. During this time, I managed a team of over 100 senior developers and navigated the challenges of competing with tech giants like Amazon for talent. It was a very educational experience.
Sofia: “You must have seen the world of tech and development evolve during your career. What was it like for you, getting started?”
Des:
Back in the day, when I was a developer, we did everything. We handled business requirements, capture and design, data, front-end, back-end – the whole package. This comprehensive experience was invaluable. You really learned by osmosis, you know? You were exposed to everything and you picked up so much by just being in the same room as senior people.
My transition from technical roles to leadership evolved naturally as my team grew. When you start with a small team, everyone knows what needs to be done, but once you hit about 20 people, everything changes. You’ve got all this talent, and you need to think about really making the most of it.
You have to start thinking differently about structure and leadership, and the bigger business picture. It was during my MBA around 2016-2018 that I began to change my perspective from being very ‘tree-focused’ to seeing the forest instead.
Sofia: “That sounds fascinating. How has the industry evolved since you started your career?”
Des:
I've seen several significant changes. The most obvious one recently is very much the shift from co-located teams to remote work, which was accelerated by COVID-19. You had guys in the treasury who’d always said “hell no” when working from home was suggested, and COVID obviously completely changed that. I’m also definitely seeing an evolution of work culture, moving away from traditional 9-to-5 schedules and fixed locations which goes hand in hand with being at home.
Because of this I think team structures are changing - we’re seeing a bigger gap emerge between junior and mid devs and senior developers, and I think that AI and automated tools have played - are playing - a big part in that.
In many ways, these changes are good! What really frustrated me in traditional corporate environments was seeing talented people only using their specialist skills maybe 30% of the time. Traditional working roles kept people pigeonholed, but there was a benefit to working in a co-located office - you’d get to see everything going on and you’d learn by exposure.
Big companies need to think about how to get your developers in the same space at least some of the time, or the gap between your junior devs and your senior experts is going to get harder to bridge.
Sofia: “Where do you see the future of the industry heading?”
Des:
I think we'll likely see the emergence of AI agencies and specialized AI tools for different aspects of development, from quality assurance to UI design, but I do think that the AI tools will enhance rather than replace human developers.
That said, I see two major challenges facing the industry and as mentioned, one of those is junior developer growth. In a co-located environment, your junior devs naturally learn through osmosis - overhearing discussions, observing problem-solving approaches, and having impromptu learning moments.
We're still figuring out how to replicate that in a remote environment, but Cloud Employee’s approach to team integration, peer review, and their co-located offices are definitely creating a team environment while enabling devs to use their specialist skills.
Sofia: What do you see as the biggest goals and responsibilities of a CTO today?
Des:
One of the first things is being able to communicate a vision to your team, and create a culture that helps them feel empowered. I think any good CTO needs to focus on vision, culture, and business acumen. From my perspective, success isn't measured by how many decisions I make, but by how many good decisions the team makes without me.
I also think that CTOs need to be translators between business and technology. The old model of the CTO being just the most technical person is outdated. Today, it's about understanding the whole business context, from financial implications to market dynamics - and communicating that to your team in a way that makes sense and helps them make those good decisions.
Maybe this is a personal thing, but I'm really passionate about frugal innovation. It's about creating efficient, sustainable systems that make the most of the talent you have while minimizing waste of all kinds. The goal is to build an organization that can function effectively even when I'm not there, you know?
Sofia: "Anything else you’d like to add?”
Des:
I think if you focus on building strong relationships within your team and understanding the business context of your technology decisions, you’ll be on your way to creating an environment and culture where your team can grow and innovate independently.
Success as a CTO isn't about being the smartest person in the room - it's about enabling others to do their best work.
Des Matthewman
