Jason Jack is the Director of AI Engineering at Holiday Extras, leading AI strategy, platform modernisation, and the engineering transformation needed to carry a 40-year-old business into an AI-native future. He joined the company in September 2025 and sits on the Product & Delivery Leadership Team.

My team focuses on AI strategy, platform modernisation, and the engineering transformation needed to carry Holiday Extras into an AI-native future. We aim to embed AI into our engineering DNA now — building the harness around AI models that will let our systems continuously self-document, self-test, and resist architectural decay.

My Role at Holiday Extras

I lead our AI engineering teams, with a focus that is threefold. I authored the enterprise Platform Plan and am leading its execution — the strategic, incremental replatforming of the mission-critical systems that serve millions of customers every year. I am designing the agentic AI harness that wraps the engineering organisation with AI-powered tooling. And I am driving AI adoption across every engineering team, from AI-assisted code review to secure, Slack-integrated agentic assistants for operational workflows.

I have been writing production code since the 1980s and have been early to every platform shift since — internet protocols in the 1980s, web development in the 1990s, internet television in the 2000s, mobile in the 2010s, and artificial intelligence in the 2020s. Thirty-five years of deep technical work across assembly language, Pascal, C++, Java, C#, Python, Swift, and TypeScript. My mantra: the harness around AI models matters more than the models themselves. The organisations that will thrive are the ones embedding AI into their engineering DNA now — not waiting for it to be easy.

Life Before Holiday Extras

Before Holiday Extras, I spent nine years as CTO and Head of AI Research at Rights Tracker, where I led AI research initiatives that delivered documented 10x productivity improvements across senior development teams, redesigned core processing from hours to seconds, and achieved 99.95% availability on mission-critical platforms.

Earlier in my career I co-founded Narrowstep, a pioneering Internet TV platform I grew from three people to a $50m IPO, serving 20 million videos a month to clients including ITV, Virgin Media, Nike, and Telefónica. I have held CTO roles at sports analytics, video processing, mobile telecoms, and telecommunications startups; architected data systems for News Corporation; led a 30-developer international team for State Farm out of Seattle; run VP of IT operations for US Government and Lawrence Berkeley National Laboratory contracts in San Francisco; and managed global technology infrastructure for an $8bn WPP advertising group across 36 offices.

I started out writing commercial games in Z80 assembly for the Sinclair Spectrum and programming inter-bank financial transaction switching systems in Pascal and 68000 assembly. I studied Physics at the University of Manchester.

Life Aside From Work

I am passionate about astronomy, robotics, and scientific research, and I maintain an active fitness regime. In my spare time I build my own AI infrastructure. I believe the best technology leaders are the ones who never stop writing code.

Inspiration

I have been writing production code since the 1980s and I find inspiration in the relentless pace of change in technology — and in the people who stay curious enough to keep up with it. I am driven by the belief that the organisations embedding AI into their engineering DNA today are the ones that will define the next decade of travel.