
Fireside with Founders & Leaders · 2026-06-10 · 55 min
Travelopia, a PE-backed portfolio of eight travel business units serving 230,000 customers annually with $1 billion in revenue, has progressed through distinct transformation phases. Chris Storey explains how the company evolved from dealing with legacy tech debt and on-premise infrastructure (Phase 1) through customer-focused digital transformation with CRM platforms (Phase 2) to its current AI-driven phase (Phase 3). The critical insight from Storey's perspective is that deploying AI technology - evidenced by his own experience building a production application in four hours using Claude and Cool Code - is comparatively straightforward. The harder challenge involves organizational transformation: redefining roles, establishing governance frameworks, managing information security, and driving adoption across non-technical teams. Storey identifies "business technologists" (people with strong business acumen and AI curiosity) as key change agents and emphasizes that AI transformation must be led from the top, with executive commitment from the CTO and Chief Executive. The company's evolution from large squads (8-12 people) to smaller, more numerous squads reflects this new operating model - delivering more output with smarter resourcing enabled by AI tools like Copilot and Claude, rather than pursuing cost reduction.
He spent 30 minutes building a detailed prompt with ChatGPT to refine an idea he had, then partnered with a colleague who used Cool Code (an AI coding tool) to write 100% of the code, resulting in a functional application ready in approximately four hours total.
Phase 1 focused on legacy tech debt and on-premise infrastructure modernization; Phase 2 involved digital transformation with customer experience improvements and CRM platforms; Phase 3 centers on AI-driven organizational change across the business.
Organizations that scale AI require top-down leadership commitment from executives like the CTO and Chief Executive, support for meaningful impact beyond personal productivity, and identification of "business technologists" who combine business expertise with AI curiosity to drive change at scale.
The company moved from large squads (8-12 people) supporting single business areas to smaller, more numerous squads with fewer engineers and QA roles, enabling higher output per person through AI-assisted development rather than reducing overall headcount.
Business technologists are people with deep understanding of business processes and operations who also have curiosity and willingness to experiment with AI; Travelopia partners them with tech teams to scale AI adoption beyond individual productivity to meaningful organizational impact while maintaining proper governance and security.
Computed from the transcript - who did the talking, and the words that came up most.
In this episode of Fireside with Founders and Leaders, host Rupert McSheehy sits down with Chris Storey, the Technology Director at Travelopia, to discuss the transformative journey of the company in the realm of artificial intelligence. With over 11 years of experience at Travelopia, Chris shares insights into how AI has revolutionized their operations and enhanced customer experiences. The conversation dives deep into the challenges and successes that come with implementing AI in a private equity-backed environment, emphasizing the importance of leadership support and a culture of experimentation. Chris elaborates on the three phases of transformation that Travelopia has undergone, from addressing legacy technology to embracing digital and now, AI-driven solutions. He candidly discusses the lessons learned from both successful experiments, such as AI-enhanced sales processes, and those that fell short, like early chatbot implementations. The episode highlights the necessity of balancing technological advancements with human involvement, addressing the potential for resistance within teams, and fostering a culture of curiosity to ensure that AI is used to its fullest potential.
Transcribed and scored by The B2B Podcast Index.
you're listening to the Far Side with founders and Leaders Podcast the podcast that gives you a behind the scenes look of some of the world's most amazing founders and leaders looking at their journeys and how they got to where they are today hello everyone and welcome to the latest edition of the fireside with founders and leaders podcast today I am joined by the brilliant Chris Storey who is a tech director over at a company called Travelopia so Chris has been there for over 11 years so he knows the company inside out and but he's seen some massive changes especially over the last few years where we've been through transformation Travelopia is effectively is a P E backed and owned organization and so we talk a bit about sort of what it's like to to be in that type of environment but really delve deep into how they've been transforming the business utilizing AI to deliver more outputs working with their software teams their engineering teams and empowering the rest of the business to be able to get the benefits that they see today through AI loads of really interesting insights and nuggets in this one so I know you're gonna love it all that's left for me to do is to let you sit back watch and listen and enjoy hello Chris welcome to the podcast good to meet you yeah good to meet you too a glorious sunny day in London in what is currently an air conditioned podcast studio so a bit of relief from very much the sun typically we like to complain about it being British but yeah lovely to have you here today thank you for making the effort and the journey to come in and we've had a conversation off air talking about some of the things we're gonna discuss today so I'm actually really looking forward to getting into some of these topics it'll be of no surprise to to most people it'll involve some AI along the way but the things that we've been talking about your relatively sort of far into your your exploratory journey um and again we'll get into some of that later but that if you could start by introducing sort of who you are a bit about Travelopia as well for those that don't know about the business and we'll go from there okay great so my name is Chris Story I'm a technology director for Travelopia I've been at Travelopia for 11 years actually yep as it happens yeah yeah in a few different roles and I'm a technology director so essentially that means I spend most of my time partnering with the businesses in our portfolio making sure I understand what they're trying to achieve what their business outcomes what are their aims and then helping to translate that into a a roadmap and a set of activities for our technology team um I sit as part of the tech leadership group and partner with uh two other technology directors so yup Shree who's in India who looks after all of our engineering and product and and Kaz who looks after our information security and we all work for our CTO who's Mike yup so so yup so so that's me and and Travelopia most people haven't heard of actually travelopia is a portfolio of travel businesses we were created I guess off the back of a sale from thwii so most people have heard of thwii yup large sort of German um tour tour operator uh it was about eight years ago now I think yeah we we had that about right yeah that sale feels like a long time ago yeah yeah lots changed and yeah so we created a travel operator at that time so so we brought together some of the smaller uh compared to two e specialist travel brands into a portfolio and we've got about eight uh business units yup in our group uh about 20 or so brands uh we serve about 230,000 customers a year yup in them on trips uh we're about $1 billion of revenue um so sort of big enough to be interesting and exciting but too small you know so it's a nice sort of sweet spot and yeah so some of the businesses in our portfolio we have a business called Quark Expeditions so quark do Arctic and Antarctic a trips on um on the three vessels that we that that we have in the fleet which is amazing a TCS which is a private jet so we have two uh Airbus A THREE TWENTY ONE jets okay we will fit it out nice and you can go on some incredible uh trips if you can afford it um but then we also have uh some yacht charter companies so sunset and the mornings are two of the largest yacht charter companies in the world we have Le Boat I'm at I'm at the risk of listing every yeah yeah yeah yeah and then I'll be in trouble for the ones I forget yeah yeah Exodus Le Boat Enchanting Travels Kay Loss Golf yeah so poor them lots of variety lots of variety yeah and generally experiential yeah experiential sort of trips for people to go on so do you get to go on any of these these trips as I yeah I've been on a few yeah um unfortunately not the TCS trip around OK around the world uh but yeah it's a great uh industry sector to work in yeah I'm sure but there's plenty more on the bucket list maybe at 12 years they they'll give you something it's a commitment to service we'll see we'll see and you mentioned so P backed right as an organization and we talked about a bit about AI transformation it's been a big part of the the work that you've been doing recently over the last well certainly the last two three years I think even even you're further back than that yeah um like can you talk to me a bit about the importance of your transformation in an organisation like yours especially given that you're you're pee backed because it can't just be experimentation you've got to be commercially focused and minded yeah so talk to us a bit about you know the the drive and some of the things you're doing yeah so it it it is and whether we're talking about AI or just transformation in general actually that that that's a journey particularly with AI sure last three 3 years or so but actually if you look during our sort of ownership the transformation journey itself has been fantastic and and we we often talk about three phases of transformation that we've been on okay you know the first phase was about dealing with just some of the legacy uh sort of tech debt type type stuff so you know a a lot of on premise uh yeah infrastructure old applications not necessarily talking very well to each other so the first phase of our transformation was dealing with that mm hmm second phase we sort of refer to as the digital transformation bit yeah so that's where we really focused on no customer experience websites um you know making the most of CRM platforms getting the data plumbed in together that now it feels like we're in the third phase yeah which is the the AI phase right yeah OK yeah everything that we're doing in and around AI and and you know as you'd expect I think most businesses are on this journey yeah it's interesting sometimes when you speak outside uh of your normal bubble right and you sort of interact with other companies I think we're I think we're doing well yep our journey and but but we're by no means experts yeah OK I certainly can't sit here today and say I'm an expert you know we know we have all the answers we're figuring it out pretty much like most people yeah I think at the moment yeah I think that's fair but yeah but we've got you know a healthy mix I think of experiments proof of concepts so the curiosity mm hmm emerging across the business yep and but then we have um some things that we've scaled uh plenty of things that haven't quite worked yep you know I I think a good mix but we're actively managing it as a as a portfolio of change OK and as a transformation journey in itself so I think we're sort of positioned well but there's so much so much more to learn and to do and to achieve it's gonna be an interesting journey there's lots going on at the moment as you say I think like when you start actually speaking to people you realize that no one's got a clue everyone's still figuring it out it's the reality of it all yeah um there are people that will try and sell you a product saying that they figured it all out but I don't think they have at all they're just trying to sell you their product yeah which is fine like that's how that's how it goes in business yeah um and it's so it's interesting to hear that even though you're quite far on the journey you're still in that that sort of zone of like figuring things out like working out like where does this go but I suppose what what's your view on sort of where things are going over the next uh I don't know I don't know where to time it really next week two or three yeah the timeline yeah we can joke you know the the some it it felt like so February time January February this year we we noticed that there was a almost like an inflection point so so something changed yeah I think it was around February there were a couple of um anthropic and um open AI models launched around that time yeah particularly in our software engineering so landscape really became truly transformational I'm reminded of there's a there's a great article um Greg Schumer I think the kind of um you know and he and he and he talked about this is in the middle of February he talked about things are going to change yup and he talked about how you know for software engineers and and software engineering and product development we've kind of been on this AI journey now for two two three years and and as a piece of transformation that's affected those teams significantly right now it's about what what next yeah you know it's about finance it's about legal it's about you know every part of the organization um and and so that's that's where we are where where are we are at at the moment actually in Travelopia is that you know we've been through huge transformation of our technology function mm hmm terms of how we go about software engineering and product um now it's about actually what else what next where outside in the organization and how do we take the learnings that we've been through as a team yeah and make sure that we can help to lead the charge with the with the rest of the business nice and when we spoke uh previously you mentioned something to me that that sort of stuck with me you said the technology that's the easy part right so I wanna dig into like what do you mean by that because I think I know yeah but it'd be great to try and sort of understand a bit more about at your sort of you know drive again towards towards that sort of stuff I think if if you look at it in the context of where we are as a technology team I think it becomes apparent I when I look at AI now and the way we use it in our software and product teams I am 99.
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