I joined Checkatrade just over a year ago. In that time, our team has undergone a dynamic digital transformation; retiring monolithic systems, scaling incident management, launching a new consumer app, and embracing AI.
Was it easy? No. Nope. Not at all. No way. Was it worth it? Oh my gosh yes. Here’s how we tackled the past, stabilised the present, built for the next, and set our sights on the future.
🏗️ The Past: Heritage Switch Off
Let’s start with the not-so-small matter of a .NET monolith we call Heritage. 100’s of services, IIS sites, and thousands of DB tables. Picture a giant, creaky machine that touches everything—from billing to data handling, from front-end queries to behind-the-scenes processes. Turning it off was never going to be as simple as flipping a switch. Instead, we had to break off pieces one at a time and migrate them to modern services on cloud-native infrastructure.
It was a giant game of digital Jenga with 20 players at once, but by pulling out the right blocks in the right order, we managed not to topple the tower. And the payoff is huge: it will drastically reduce operating costs while removing a massive blocker to innovation. The best part? We can now build cooler stuff without an ancient monolith looming over us.
Read more: How We Decommissioned Heritage (Without Toppling the Tower)
🛠️ The Present: Incident Management
While we chipped away at Heritage, our teams were deploying features faster than ever, and occasionally letting slip the odd bug (it happens to the best of us). That’s where incident management came into play.
We migrated from OpsGenie to Incident.io, consolidating our on-call processes. No more guesswork about who’s holding the pager at 3 a.m. or what’s happening. We have it down to a science.
The key was recognising that a faster-paced deployment schedule inevitably increases complexity. By investing in incident management before we needed it, we saved ourselves from future chaos.
No one likes incidents, but our polished process and lightning-fast communication meant minimal downtime and clear updates for everyone affected. It was (and still is) essential to “keep the train on the tracks” even when we’re upgrading the rails underneath.
🚀 The Next: A Unified Platform
With the past under control and the present stable, we also needed to build our next-gen platform. We wanted a system that enabled developers to build services without waiting on dependencies, could handle rapid deployments, and support new products without leaving our dev teams drowning in complexity.
Single API Plane
Our services rely on Kong as a unified API gateway. It streamlines everything: security, routing, observability, the works. It also created a one stop shop for where to find where to integrate with services.
Kubernetes for Infrastructure
We adopted a self-service Kubernetes approach with helm charts, letting developers spin up services at will. This reduced the wait times for new environments and made our deployment pipelines more maintainable.
Backstage for Developer Experience
Backstage gave us a single pane of glass for documentation, component catalogues, and dev tooling. Teams no longer waste time hunting down scripts in random repos (which is basically the digital version of rummaging through a messy attic).
This environment helped us deploy our new Consumer App, a flagship goal for the year. And let me tell you: launching a critical app on a fresh platform while simultaneously retiring a heritage system is about as nerve-wracking as it gets. But we did it, and it’s thriving. More importantly, it’s only the beginning. Now that we have a robust platform, we can dream up bigger products and spin them up faster than ever before.
Check out the new Checkatrade App
🤖 The Future: AI and Beyond
With heritage behind us, stability in place, and a flexible platform at our disposal, we’re leaning into AI. I want to see how AI can enhance everything from customer support to user onboarding.
Retool has made it insanely easy to make prototypes user friendly, ready to dogfood these tools internally. If something has potential, we double down.
There’s a real sense of excitement where every new experiment could spark a revolution in how tradespeople and homeowners connect. It’s early, but the energy is palpable, and I’m thrilled to be driving this forward with the rest of our talented teams.
Reflecting on the Year of Change
I’d be lying if I said I tackled this alone. We have an incredible group of engineers, product managers, designers, and support folks who all rose to the challenge. But I’m proud to have played a leading role, especially as a relatively new member of the Checkatrade family. It’s been a whirlwind of tough decisions and high-fives.
Key Takeaways
Don’t Fear the Boat Rock
When I joined, Checkatrade worried about upsetting customers by changing too much, too soon. Turns out, if you deliver value, customers will adapt.
Incremental Wins Beat Perfection
We didn’t wait for the heritage system to disappear before launching the new app. We went for quick wins, proved the concept, and gained momentum.
Enable Teams, and the Teams Will Deliver
Whether it’s K8s or AI, giving teams great tooling unlocks great levels of creativity and efficiency.
Onward and Upward
Looking ahead, we’re in a fantastic position to make good on all our future ambitions. That fear of failure? Replaced by a healthy appetite for calculated risks and innovation. The consumer app launch was just the starting line for what we can build now that we’re freed from legacy constraints.
So here’s to another year of big leaps and bold moves. Keeping the boat steady while still making waves is the new normal here at Checkatrade. It’s far more exciting than clinging to business as usual.
Cheers to 2025 and everything we’re about to build next!
Thanks for reading! If you have any questions or want to talk shop about K8s, Gen AI, incident management, or modernising legacy platforms, don’t hesitate to reach out on https://www.linkedin.com/in/jpainio/
