Talking about technology, leadership and strategy

I help build systems and teams that solve real problems. With a background in security, networking, architecture and platform engineering, I care about technology that works, scales and supports people. Here you’ll find thoughts on AI, tech leadership and building systems that matter.

From Air-Gapped to AI-Ready: The Story of PortSwigger’s Delivery Shift

A Slow System Meets a Fast World The software was brilliant. The research was world-class. The infrastructure and delivery model needed to catch up. When I joined PortSwigger, engineers were working in air-gapped environments. This was designed with security in mind, though over time it had started to get in the way. Teams often had to work around the controls just to stay productive. There were brilliant minds everywhere. We were spending large amounts of engineering effort building clever but overly complex solutions to problems already solved by open source. ...

5 August, 2025 · 13 min · 2743 words · Ben Smith

Build Buy Wait

Every team faces the same question eventually. Do we build it? Do we buy it? In my view, the answer is simple: build what differentiates you. Everything else? Buy it and move on. Focus where it matters. At PortSwigger, that means building software for security professionals, not CRMs, not invoicing systems, not things that already exist in a thousand better forms. We’re never going to out-invest Salesforce in CRM and while we’ve got the engineering talent to build one, it’s not our core business. So we don’t try. ...

26 July, 2025 · 4 min · 697 words · Ben Smith

Expert Generalists Will Win the AI Race

I’ve always needed to know the why As a child I used to take apart the toaster and washing machine just to figure out how they worked. More often than not I left behind a trail of broken appliances for my exasperated parents. That curiosity never left. It’s what led me through a career spanning helpdesk support, networks, infrastructure, solution architecture, cloud, DevSecOps and now technology leadership. I’ve rebuilt myself more times than I can count. Not for the fun of it but because it’s the only way to stay relevant when the landscape keeps shifting underneath me. ...

20 July, 2025 · 3 min · 580 words · Ben Smith