Accidental CTO: How HCD Prepared Me for Leadership I Didn't See Coming

When I joined Holiday Caravans Direct (HCD), I didn't plan on leading. I wasn't hired as a CTO or even a lead developer — I was simply tasked with rebuilding their online booking platform. But as the project unfolded, I found myself taking on more and more responsibility. Before I realised it, I was making strategic technology decisions, translating business goals into system designs, and becoming the company's go-to tech voice.

Without the title, I was already doing the job.

Ownership From Day One

There were no architects, product managers, or tech leads to lean on. Every decision came through me — from how to structure the database to how to display seasonal pricing and manage legacy API integrations.

I didn't just build the platform; I helped shape the business's digital strategy. I introduced agile practices, trained the team in SCRUM, and set realistic timelines based on available resources.

In hindsight, that was my first true experience as a CTO — even if we didn't call it that.

Learning to Bridge the Gap

A big part of this accidental leadership role was learning how to communicate with non-technical stakeholders. I had to:

• Justify timelines without hiding behind jargon

• Propose scalable solutions that aligned with business constraints

• Push back (constructively) when ideas clashed with user experience or technical feasibility

Over time, I became a translator between tech and business — a core skill of any technical leader.

Vision Without a Map

As a solo developer, I had to define the product roadmap as I went. There was no predefined backlog — just high-level ideas and a lot of trust.

This taught me to:

• Prioritise ruthlessly based on user value

• Make architectural choices that enabled future flexibility

• Avoid gold-plating by focusing on what moved the needle for the business

I learned that good leadership isn't about having all the answers — it's about making confident, informed decisions and adapting as you go.

The Mindset Shift

HCD changed how I saw myself. I wasn't just a developer — I was responsible for delivering a product that mattered. That shift in mindset stayed with me long after the project ended.

When I later stepped into formal CTO and architecture roles, I didn't feel out of my depth. I'd already done it, just under a different label.

You Might Be Leading Already

Many developers take on leadership responsibilities long before they get a title. If you're managing delivery, translating requirements, guiding stakeholders, and owning outcomes — you're already leading.

HCD was my proving ground. It taught me to trust my judgment, take initiative, and see the bigger picture. And for that, I'll always consider it one of the most formative chapters in my career.