Management

In the years at the European financial technology firm, the engineering organisation went through three significant restructuring events: a change in engineering leadership, a shift from functional to product-aligned teams, and a consolidation of two separate engineering groups. Each one produced the same kind of disruption and the same kind of opportunities. Org change is uncomfortable. It’s also underanalysed. Most engineers treat it as something happening to them, not something to navigate actively. ...

We had an incident that took down pricing for 23 minutes during the London open. High severity, real monetary impact, humbling root cause: a configuration value that worked in staging silently didn’t apply in production due to an environment variable naming collision. The postmortem process that followed was one of the better-run ones I’ve participated in. Here’s what made it useful. ...

On-call has a bad reputation in software engineering, and often deservedly so. Being paged at 3am for an alert that didn’t need to wake anyone is demoralising. Being on-call for systems you didn’t build, don’t understand, and can’t fix is terrifying. Being paged multiple times a night for weeks is a health risk. But on-call done well is a powerful practice. It creates direct feedback between the reliability of what you build and the experience of carrying it. When engineers are responsible for their own systems, they ship more reliable systems. Here’s the version that worked at the European fintech firm. ...

Every engineering team has a roadmap. Most engineering roadmaps are wrong. Not in a surprising way — in a predictable way that reflects structural problems in how they’re created. After doing roadmap planning at two companies at different scales, here’s what I think actually works and why most roadmaps fail. ...

The term “technical debt” was coined by Ward Cunningham specifically as a financial metaphor. Debt isn’t inherently bad — it’s a tradeoff: you get something now in exchange for a future obligation. When the metaphor is understood, the management of technical debt becomes clearer. When the moral framing replaces the financial one, it becomes a guilt-driven cycle that helps nobody. ...

Over two years running engineering hiring at the firm, we made about twenty senior engineering hires. Some were transformative — engineers who raised the quality of everything they touched. Some were neutral — competent contributors who did what was asked and not much more. A few were net negatives. Looking back, the correlation between interview performance and outcome was weaker than I’d expected. The things that predicted good hires were visible in the interview, but we weren’t consistently measuring them. ...

The startup had been good. We’d grown from twelve people to forty, shipped something real, and the technical foundations were solid. But the Series B had brought in a new leadership layer, the founding team’s velocity calculus had changed, and I found myself doing more coordination than building. I’d been at this inflection point before — at the institution, actually — and I recognised what came next. The new role was at a well-established European financial technology firm. Structured, profitable, engineering-first culture, around 400 people. Not a startup. Deliberately not a startup. ...

I was promoted to tech lead at the startup in early 2020. The team was five engineers, including me. My previous experience managing people: none, unless you count mentoring a couple of interns. The first month was humbling. The second month was better. By the third month I had a clearer mental model of what the role actually required and how it differed from what I’d been doing before. ...

I left a well-paying, intellectually interesting job at a large financial institution to join a company with fewer than twenty people and less than a year of runway. My colleagues thought I’d lost perspective. My family was diplomatically concerned. Here’s the honest version of the reasoning. ...