Rob Grigg

Group CTO, Holiday Extras

Rob Grigg is the Group Chief Technology Officer at Holiday Extras, where he leads the engineering, infrastructure and architecture teams to push the boundaries of AI and technology in service of real business outcomes. He believes great technology should balance ambition and delivery, always serving the business, never dominating it.

My role at Holiday Extras

I lead our technology, architecture, infrastructure, data, and IT teams. As Group CTO, I'm here to align our technology with our business vision and stretch the art of the possible while we're at it. I'm committed to building strong foundations to enable us to deliver scalable architecture, high-performance systems and AI-led innovation.

I'm a great believer that the best outcomes can be achieved by working collaboratively and empowering people with a clear strategy and the freedom to do amazing work. Innovation is only possible when you step beyond the safety barrier and voyage into the unknown and I aim to equip my teams with the confidence to purposefully experiment.

I'm currently focused on...

Right now, I'm focused on repositioning Holiday Extras as an AI-first organisation. That means more than adopting new tools — it's about reshaping how we think, work and deliver across the business. We're embedding AI into the fabric of our platform, using it to automate intelligently, enhance personalisation, and unlock new opportunities for growth and efficiency. To support this shift, I'm also leading a simplification of our technology stack — rationalising legacy systems, reducing complexity and ensuring we have a modern, scalable architecture that's fit for the future. I'm building a cross-functional architecture team, including principal engineers and solution architects, to create the strong technical foundations needed to accelerate innovation and deliver with confidence.

Life before Holiday Extras

Technology entered my life early with the legendary ZX81 and I was fifteen when I wrote my first piece of commercial software. I never cease to be excited by the potential to push the boundaries of what's possible.

My skills have proved to be flexible and adaptable, working in companies ranging from start-ups to large-scale enterprises across a variety of industries, from energy trading and insurance to eCommerce and fintech.

Some highlights include:

• Delivering many large scale solutions for Virgin Atlantic, Experian, Lloyds of London and The conservative party whilst working at Conchango
• Leading engineering and architecture at online retail giant ASOS during a period of unprecedented growth
• Driving customer-focused delivery for embedded finance solutions as Global Vice President at Railsbank (now Railsr)
• Consulting on complex architecture and delivery as an interim CTO across a variety of businesses

I've also co-founded and served as CTO for my own ventures and projects.

Life outside Holiday Extras

You won't be surprised to hear that tech plays a major part in my life outside of work too. In my younger days I was a semi-professional drummer in a band called The Dentists (look them up on Spotify!) and I have built a recording studio at the bottom of the garden where I can geek out to my heart's content!

I still play the drums occasionally in a local band, but I'm most inspired these days by helping other performers record their music and get it out to the masses. I'm a self-taught engineer and can mix and master tracks, which I often offer to do free of charge to give bands a helping hand.

I also hold a black belt in Wado Ryu karate (don't ask to see my moves, I'm a bit rusty!) and I love cooking for family and friends, which might be the only time I'm fully offline.

What's your perfect hassle-free holiday

When it comes to holidays, my attention to detail kicks in and everything must be meticulously planned. For me, it's about having a seamless experience, no queues, no delays, and everything working like magic in the background. I love exploring somewhere new, but I make sure I put the work in beforehand to eliminate as much of the stress as possible. A combination of a tech-enabled smooth trip (of course!) and a bit of luxury doesn't go amiss.

Inspiration

I'm inspired by imagining the impossible and trying to make it happen. I believe reaching for the stars is an honourable aim - even if I fall short, I've given it my best shot.

And while we're talking about stars, I'm captivated by cosmology and the origins of our universe. Nothing is more awe inspiring than staring up into the vastness of the night sky. I've just heard about a star ranch in Texas with unparallelled views of the galaxy - you might find me heading there one day soon!

At work, I'm inspired by good design, big ideas and the moment when a great team clicks. The best leaders make space for others to grow. Whether I'm writing code or building a strategy, I'm driven by the same goal: to make things that matter, with people who care.