ben.milleare
About

Hi, I'm Ben.

CTO and technical leader. Polymath by accident, generalist by choice, opinionated about the boring middleware that makes things actually ship.

Fully booked

We can still talk, transient engagements in my downtime could still work.

I've been building and engineering for the better part of twenty-five years, and leading technology teams for the last fifteen, mostly as the technical leader founders put their trust in to steer things in the right direction. In between, I've also solo-founded, bootstrapped and sold businesses too - most recently a DaaS that reached over £600k ARR.

Where this started

A lot of how I work now traces back to the late 90s and early 2000s, when I was a teenager probing systems and building tools for the sheer pleasure of finding out how things worked. It was the hacker mentality in the original sense, the instinct to take something apart, break it on purpose, and understand it well enough to put it back together differently. The difference between using a system and actually knowing it became obvious early, and it has shaped how I think about engineering ever since.

The goal still hasn't really changed: find where something breaks, work out why, and then figure out how to fix it. Most of the engineering decisions that have actually mattered in my career are downstream of that single instinct, and most of the engineers I trust the most are the ones who share it.

The path so far

My first real end-to-end technology project came at High Position, one of the UK's earlier search-marketing agencies, where as Technical Director I designed and built their in-house digital marketing suite from scratch with a single developer reporting in. I had been running the technical SEO channel already - working directly with some the UK's largest household brands. That work gave me a deep grounding in digital marketing that I still lean on today, and a healthy respect for the gap between a clever idea and software that actually does the job.

From there I worked my way up through agency life and into engineering leadership at high-growth startups. The most formative chapter was a Buy Now Pay Later platform where I scaled the engineering team and helped shape the architecture that sat underneath it, and by the time I left the systems had processed just shy of a billion pounds in payments. The clever architecture mattered, but most of what made it work was getting the unglamorous things right, the stuff nobody puts in a deck.

What I work on now

These days I work as a fractional CTO with founders who have technical instincts but need someone who's already lived through the next eighteen months. I do my best work when the role is shaped as a CPTO, where product strategy and engineering decisions sit with the same person rather than being scattered across teams that aren't yet talking to each other properly. The mandate is usually a mix of strategy and pragmatism: pick the right architecture for the company you actually are rather than the company you imagine becoming, hire engineers who can do the job today and grow into the one tomorrow, and keep the AI ambition tethered to a business outcome you can defend in a board meeting.

The stack I reach for first is Linux, PHP / Laravel, Postgres, Temporal (for anything that has to be durable), and a respectable mix of TypeScript, Vue, Rust, and Python depending on what the problem actually wants. AWS is my cloud of choice. I'm comfortable in the AI weeds too, from Claude and the GPT family through to Llama, Qwen, and the open-weight world via Ollama, with the orchestration layer mostly built around Temporal, n8n, and whatever LangChain hasn't deprecated this week.

Web3 and the on-chain future

Crypto's been a personal obsession since I bought my first Bitcoin sometime in 2013, back when it still felt like a curiosity rather than a category. If only I'd decided to just HODL. These days I write Solidity, ship the occasional smart contract, and remain stubbornly bullish on the on-chain future against pretty much everyone who insists the whole thing's a passing fad. The plumbing keeps getting better, the use cases keep getting harder to dismiss, and the next decade of fintech is unlikely to look much like the last one.

Beyond client work

I'm an Associate of the Agentics Foundation, which keeps me close to the people pushing on safe, autonomous multi-agent systems before those patterns make it to production elsewhere. I'm also writing a book called The First-Time CTO, which is roughly the field guide I wish someone had handed me about a decade ago. Most of the rest of my thinking lands in Notes, where I write about the patterns I keep reaching for and the mistakes I keep watching teams repeat.

Away from the Internet, I've been married for 20 years to my lovely wife Adele and we have three fantastic children together. I'm a bit a petrol head, a season ticket holder at West Ham, and also a keen swimmer - covering around 7-8 kilometres a week in the pool.

If you're reading this

You're probably here for one of three reasons. You're an early-stage founder wondering whether a fractional engagement makes sense before you commit to a full-time CTO. You're a growth-stage operator with a specific problem (AI strategy that hasn't made it past proof of concept, an engineering team that isn't scaling like the head-count chart suggests it should, an architecture decision you don't want to get wrong twice). Or you're a fellow technical leader who just wants a sounding board for something tricky. Any of those works. Drop me an email and we'll see if there's a fit.