From bootstrap to multinational acquisition: scaling an insuretech engineering org

The situation

A UK insuretech SaaS, early stage, with a small founding engineering team and a product that was starting to win bigger customers. The next stage needed three things at once: a team that could deliver faster, the compliance posture to win enterprise contracts, and a platform that wouldn't fall over while both of those happened. I led engineering through that whole arc, from early stage to acquisition by a multinational.

What I did

Grew the engineering team to 20+ engineers across the UK, EU, and the Americas, with the hiring, structure, and practices to match: agile delivery, daily CI/CD, and a move to cloud-native infrastructure.

Led ISO 27001 certification end-to-end. Scoping, gap analysis, implementation, accreditation, all while the team kept shipping. That certification directly unlocked the enterprise contracts the business was chasing.

When the acquisition came, I ran the full technical integration: migrating infrastructure, aligning engineering practices across the combined organisation, and keeping delivery moving through the transition.

Through all of it I stayed close to the code, shipping production software in Node.js, TypeScript, and React while leading the team. In the later years I designed and built LLM agents that automated the full agile workflow, sprint planning, backlog refinement, standups, retrospectives, and release documentation, plus RAG-based tooling for internal knowledge retrieval and decision support.

The outcome

The business went from bootstrap to acquisition by a multinational. The platform held 99.95% uptime through the scaling period. ISO 27001 landed and enterprise deals followed. The LLM agents and RAG tooling drove a productivity lift of around 25% across the team, measured, and visible in delivery.

The pattern I'd point other founders at: technical leadership works best when the person setting the standards is still subject to them. I reviewed the architecture, ran the hiring, and shipped code in the same codebase as everyone else, every week.