The Technology Scaling Trap: What Got You Here Won't Get You There
From travel website to Google's AI benchmark: How shifting technology mindset transformed loveholidays
Last October, I was attending Google Cloud Summit (their largest conference outside the US) when something surreal happened: their MD of AI opened his keynote by talking about loveholidays.
Not about a tech giant, not about a Silicon Valley darling, but about a travel company from Hammersmith (which can barely be classed as London). He held us up as their benchmark for innovation. It was a moment that would have been unimaginable 5 years earlier.
Rewind to early 2019 and loveholidays was sat proudly on top of the Sunday Times Profit Track 100 list but our technology was struggling to keep pace with the scale of the business.
Again, we’d found ourselves living through a "Papa John's moment" where an undiagnosed technical issue had brought trading to a crawl. It was yet another weekend where the team was camped in the boardroom trying to find out why, fuelled by stacks of the titular greasy pizza and Red Bull. I had just started as the new CTO and had to face the daunting challenge of convincing the fastest-growing business in the UK that its technical approach had become our biggest liability.
Success at scale demands a different kind of thinking.
Recently, I'm recognising a familiar pattern—it's time to challenge our assumptions again.
You Think You've Reached the Summit, Only to Find Another Mountain
That's what scaling a fast-growing technology business feels like. Each peak you conquer reveals a bigger challenge ahead—and the approach that got you up one mountain won't get you up the next.
The numbers tell a stark story:
Only about 1% of seed-funded startups ever reach unicorn status
2023 saw just 143 new unicorns globally—a 54% drop from the previous year
The journey takes a median of 6 years for those who make it
Many promising companies stumble—not because their core idea was wrong, but because their technology couldn't scale with their success.
Our experience in scaling mirrors what LinkedIn founder Reid Hoffman describes in 'Blitzscaling’, where new scale thresholds require a shift in company priorities and operational approaches.
What I've learned is that different phases of growth require fundamentally different approaches to technology. Our journey at loveholidays has traversed 3 distinct phases—startup, scale-up, and now scaling out (market expansion)—with each transition requiring a deliberate shift in how we think about technology.
Phase 1: The Startup – Finding a Business Model
In the startup phase, loveholidays focused on establishing a viable business model. The approach to technology was straightforward:
Build just enough to validate ideas quickly
Move fast and cut corners where needed
Run from a prioritised to-do list
Rely on a small team of generalists
This approach was perfect for the startup phase. It allowed us to experiment rapidly and find our market fit with minimal resources. But as we succeeded, the limitations became increasingly apparent.
The First Shift: From "Travel Company Using Tech" to "Tech Company in Travel"
I will never forget one of my first meetings with our new CEO, Donat Rétif. He joined just as loveholidays reached its first peak—it had a proven business model but was struggling with its own success.
The startup technology environment had created a complex and opaque system with serious constraints:
We deployed changes just once daily (never on Fridays)
High-traffic periods triggered code freezes to avoid breaking things
Low-traffic periods also triggered code freezes as we didn't know if something was broken
In one particularly painful instance, leadership scrapped months of work because trading numbers dipped for a few weeks
For developers joining us today, this approach sounds like a nightmare. And from a technical perspective, it was.
Every spike in traffic was a crisis. Each new feature risked breaking something else. Our startup thinking had become our biggest limitation.
That's when Donat said something that became the catalyst for change:
"We need to stop thinking of ourselves as a travel company that does technology and become a technology company that happens to be in travel."
This wasn't just a clever phrase—it was permission to transform how we approached technology. But transformation requires more than permission—it needs a deliberate approach.
Our transition focused on 3 key areas:
Balancing Skills - We brought in specialist technical expertise to complement our business domain knowledge, creating teams that could tackle complex technical challenges
Defining Shared Principles - We established 5 technology principles (detailed in a previous article) that would guide our decisions and create alignment across growing teams:
Think big, deliver incrementally
Invest in simplicity
Leave things better than you found them
Focus on differentiation
Technology is a means to an end
Adapting Our Structure - We moved from a centralised, project-based approach to cross-functional teams organised around business problems.
This professionalisation was essential for scale. It gave us the foundation to handle increasing complexity while maintaining our ability to move quickly. These fundamental changes, shift in mindset and approach unlocked the next stage of extraordinary growth.
Phase 2: The Scale-up – Unlocking Exponential Growth
Our next phase was all about leveraging the foundation we'd built to handle scale far beyond what was previously possible.
Success brought unprecedented demands:
More website visitors - we handled more sessions in a month than we did in the entire year before I joined
More bookings to manage - last year we sent the equivalent of 1 in 17 people in the UK on holiday
More teams working in parallel - to keep up with our growth we have had to double the size of our technology team—though we try as hard as we can to limit this
With our new approach in place, we achieved results that would have been unthinkable before:
Nearly 250,000 system changes annually: developers' output multiplied 7x, non-technical teams contributing independently, and AI automating a significant portion
Zero outages despite January 2024 traffic exceeding our entire 2019 volume—we now routinely load test to 10x capacity each night
Our most mind-blowing achievement? Our search now pre-computes 6 trillion packages per run. We processed 1.4 quintillion packages last year alone—more than all the grains of sand on every beach in the world.
An important lesson from this transition: it's easy to be critical of the past, especially when you weren't part of it. The approach that seemed limiting now was exactly what the business needed in its earlier stage. Each phase requires its own mindset—and it was this understanding that helped us change again.
The Second Shift: From Scale-up Systems to Platform Thinking
As always, our CEO was one step ahead of the business. For a few years, he had been talking about the need to think again about how we operate.
The crucial lesson keeps emerging as we grow: what got you here won't get you there.
We've now entered our third phase—market expansion—moving beyond UK short-haul beach holidays to:
Multiple countries: Ireland, Germany and Austria, with more to come
Diverse product types: City breaks, long-haul and other emerging categories
Various customer segments: Couples, families, and other distinct groups with unique needs
When you do the maths, we're looking at 160 different customer cohorts to serve effectively.
Scaling our previous approach to cover all these cohorts would be impossible. We'd need to clone our teams 160 times over.
Instead, Donat pushed us toward our second major mindset shift: thinking of loveholidays as a platform business.
This is where things get considerably more abstract, and I've learned that creating a shared vision is essential when dealing with this. As someone with aphantasia (no visual memory) I've come to rely heavily on diagrams to communicate these ideas.
One way I have come to think about our platform is as the "car that gets us to the destination"—in this case, the means of serving 160 customer cohorts across markets. The system is the platform that makes this possible without requiring 160 separate teams. Having a version of this that we all understand is key.
Our approach to this transition focuses on:
Creating a Unified Platform Vision - Building shared mental models across the organisation so everyone sees how their part contributes to the larger system.
Continuing to Evolve Our Structure - Shifting from domain-specific teams to capability teams that can support multiple markets and products
Implementing Configurable Systems - Building core capabilities once that can be adapted for different markets without requiring custom development.
This shift is fundamentally changing how teams think about their work—moving from "How do we solve this specific customer problem?" to "How do we build capabilities that empower others to solve many similar problems across multiple markets?"
The Ripple Effects: Beyond Systems to People and Markets
These technological shifts have had 2 remarkable consequences that extend beyond our systems.
Changing Work
The evolution has changed not just our systems but what work looks like at loveholidays.
Juliana's journey exemplifies this transformation. She started in our contact centre, moved to QA, and in doing so gained a deep understanding of customer needs—but the operational constraints meant implementing solutions was painfully slow.
Eugene and Tom, who were reimagining our Contact Centre platforms, recognised the need for someone with her skills to help build the systems in the most effective way. So they invited her to join the Conversational Design team working on Sandy, our AI assistant.
In her own words:
"In CX, it was often about accepting that something was a problem. In Tech, it's more proactive—identifying the right people, explaining the impact on customers, and pushing for better solutions."
Combining her customer understanding with the new technical capabilities allowed her to have a much bigger impact than before—helping us automate 50%+ of chats and 20%+ of voice contacts. She is also now playing a pivotal role in repeating this success as we scale into new markets and languages.
This pattern is repeating across the business. Everyone at loveholidays is now working in technology, whether directly building it or using it to tailor experiences.
Transforming the Industry
Our approach is also starting to change the travel industry itself.
In late 2023, there was a significant shift in how Ryanair worked with Online Travel Agents (OTAs), implementing changes that made it challenging for many OTAs to continue offering their flights.
While some in the industry pursued adversarial approaches, our "technology company" mindset led us to pursue a different path—focusing on mutually beneficial collaboration. We initiated conversations with Ryanair, centered on how we could work together to best serve our shared customers.
These productive discussions revealed alignment in our goals. Both parties recognised the opportunity to create something that worked better for holidaymakers while respecting each company's business needs.
What followed was a true technical collaboration. Our engineering teams worked alongside Ryanair's technical staff, and together we implemented an integration in just 3 weeks. This partnership approach made us the first OTA to establish a new ‘verified’ booking relationship with Ryanair.
This demonstrated to the wider industry how technical partnerships between airlines and OTAs can create value for everyone involved—especially customers. It reinforced our belief that putting customer needs first while finding technical solutions is almost always more productive than confrontation.
Yet even as we celebrated these successes, past experience ensured that we have never rested on our laurels. Because there is only one certainly in travel: you are always approaching another inflection point.
The Next Mountain is Already Visible
You think you've reached the summit, only to find there's another mountain behind it. That's the reality of scaling a fast-growing technology business—a reality I've now experienced multiple times.
The pattern is clear: yesterday's solutions become tomorrow's problems. The technology approach that works for your startup will fail as you scale. The approach that works for scale-up will collapse as you expand across markets.
In a moment of synchronicity, loveholidays was showcased a second time with Google—this time at their Next conference in Las Vegas. A small part of our story was presented in front of 35,000 people, sandwiched amongst the incredible announcements of the latest advancements in AI.
There couldn't have been a more obvious signal of what lies ahead.
As this AI tornado reshapes how work gets done, the next mountain for loveholidays to climb presents a double challenge: we need to operate at a vastly different scale, while simultaneously adopting entirely new tools and approaches to get there.
I believe that the organisational adaptability we've developed through previous transformations has uniquely prepared us for what comes next. Far from the daunting prospect it was 6 years ago, I see responding to this AI-driven evolution as another opportunity for the company to leap forward, and I’m really excited for what happens next and, yes, Papa John's is still on speed dial.
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Which Technology Mountain Are You Climbing?
Which mountain is your organisation climbing now? And more importantly, are you still using the gear that got you up the last one?
I'm genuinely curious about your experience with these transitions. Did you struggle to scale agile and abandon stand-ups and showcases? Was it hard to convince the business to break apart the monolith? What was the most unexpected lesson you learned?
Share your thoughts in the comments—I'd love to compare notes on how different businesses navigate these challenging shifts. Or if you'd prefer, reach out directly and we can discuss how our loveholidays journey might provide useful parallels for your situation.