Meet Simon

For Simon, progress comes from doing, not overthinking. Guided by the mindset to “ship it and iterate,” he believes the fastest way to learn is to put something real into the world and improve it from there.

A working prototype beats a perfect plan every time. It gives people something concrete to react to and that’s where the best ideas tend to emerge. It’s a mindset that shapes how he approaches his work at Checkout.com: practical, fast-moving and always focused on impact.

Why Checkout.com?

Simon joined Checkout.com for the opportunity to shape how AI is developed and adopted across the business, at a time when the AI Centre of Excellence was still being built.

“It wasn’t a predefined role. It was a chance to define the direction from the ground up. When you spot a problem, you can go and fix it and that compounds. The more you deliver, the more latitude you earn and the more interesting the problems get.”

It creates a kind of flywheel: momentum builds, scope expands and the work keeps evolving.

Building AI That Matters

Simon’s work sits at the intersection of technology and real-world application where success is measured by what actually changes.

Recently, he partnered closely with Finance to deliver an agentic document analysis system. A process that once took around two hours per review can now be completed in about fifteen minutes. But what matters just as much as the outcome is how the work happens:

“We sit with the people who have the problem, we build something that actually solves it and we measure the impact.”

There’s no interest in building AI for the sake of it. The focus is always on applying it where it genuinely moves the needle.

‍Collaboration Without Boundaries

One of the things Simon values most about Checkout.com is how naturally collaboration happens across teams..

“It’s not ‘tech builds, business waits.’ We’re solving it together, iterating in real time, with both sides shaping the outcome.”

That environment shapes how he works. Rather than building in isolation, he brings people in early, making sure the solution is grounded in real needs from the start.

#Run Lean

“In AI, it’s tempting to chase the most technically interesting problem but that’s not always the most valuable one.”

#Run Lean acts as a constant sense check, grounding decisions in what truly matters. For Simon, that constraint is energising, keeping the work focused, intentional and tied to real impact.

“I’d rather build something focused that works than something ambitious that never lands.”

Shape the Future with Checkout.com

Simon’s experience reflects a culture where ownership is real and impact is visible. In the AI Centre of Excellence, engineers take on problems end to end. From shaping the idea through to building and deploying the solution.

“We’re hiring AI Engineers who want to build things that actually get used.”

With the team at an inflection point, still small but scaling with strong investment, there’s a real opportunity to shape both the work and the direction of AI at Checkout.com.

For those who are comfortable figuring things out as they go and motivated by solving real problems, it’s a place where you can make a tangible difference.

Interested in building AI that solves real business problems? Explore opportunities in Technology at Checkout.com and help shape what comes next.

Explore Careers at Checkout.com