AI Pioneer

PortSwigger Ltd; Knutsford; On-site; GBP 80,000 - 150,000; Full time

Benefits offered by this job

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Pension (8% employer)

Life assurance (4× salary)

Income protection

Private medical insurance (Bupa)

25 days holiday + public holidays

Job summary

PortSwigger is going all-in on AI. This role is a builder who tackles hard, unscoped AI problems across the business, embedding with teams for two-week sprints and shipping real, measurable improvements.

You’ll work hands-on, evaluate outcomes, and share pragmatic tooling recommendations across domains, from legal to marketing to customer success. If you love shipping useful AI artefacts, this is for you.

Responsibilities

• Walk into a corner of the business that hasn’t cracked AI yet, spotting the agentic opportunity in things people don’t even think of as a process
• Sit alongside the people closest to the work and learn, fast, how they actually operate
• Design, build and ship a real thing - not a deck, not a strategy, an artefact someone uses on Monday morning
• Evaluate it properly: did this actually help, by how much, against what
• Help the team adopt what works - then disappear to the next domain entirely
• Build a sharp, opinionated take on which AI tools are actually best for what, and share it back across the org

Job description

The role

PortSwigger is going all-in on AI. Not as a side project, not as a slogan - as the central way we intend to work across every part of the business. This role is one of a small number of people who will help us actually do that.

It’s a role for a builder. You’ll drop into hard, unscoped AI problems across the business, usually in the parts that haven’t figured AI out yet. You’ll embed alongside the people closest to the work for around two weeks, ship something that actually makes things better, then move on to the next problem. Roving, not tribe-aligned. Always in the work, never writing slides about it.

About you

You’re fanatical about AI. It’s rewired how you live.

You wake up and check what dropped overnight - a model release, a new agent framework, a benchmark, a product launch — and if something interesting landed, half your morning’s gone to playing with it. Your weekend project is the next tool you wanted that nobody had built yet. Your home is full of little things you’ve stitched together for yourself: the budget tracker, the weekly meal planner, the shopping list that re-orders itself, the bedtime story generator for your kid or your nephew. Your browser history is release notes and changelogs and half a dozen Discord tabs.

You have personal subscriptions to several AI products and you’ve played with many more. Within hours of a new one dropping you’re inside it, and you have a real opinion by the end of the week about what it’s actually good at. You switch tools when the industry moves — you’re not loyal to anything that stops being the best.

You can’t shut up about it. Friends gently take the piss. You don’t mind, because you can see what’s coming and they can’t yet.

You’re working harder than you ever have — and loving it. The AI lever is so big that you’re getting 10x more done in 1.5x the time, and you keep finding more.

You’re probably a bit stuck, though. Your current employer treats AI as a side project — the tooling is blocked, the spend is capped, the ambition is missing. You’ve found yourself pushing for better tooling, clearer permission, and more ambition because you can see the opportunity being missed. You want to be somewhere it’s taken seriously. That’s the bit that’s going to make this role grab you.

You don’t just talk about AI — you build with it. You’ve taken an ambiguous brief, with no spec and no team, and produced a working thing under your own steam. Recently. You measured whether it actually helped, because you’re as interested in the evals as you are in the build. You leave an artefact trail - repos, prototypes, write-ups, side projects - and that’s how we’ll get to know how you think.

You travel light across domains. Drop you into legal, marketing, customer success, recruitment, operations, finance, data — and you see the agentic opportunity quickly. You aren’t thrown by unfamiliar subject matter. You work alongside the domain expert, not above them. You ask the right question to get the context you (and the AI) need to do good work. You’re good at figuring out what someone really wants, not just what they say they want. You explain how AI works in a way that lands with the person actually doing the job.

You bring energy without performing. You don’t have to be a jazzy extrovert — but you’re personally lit up by what’s possible, and that pulls people along. Sceptics walk away from a conversation with you wanting to try something.

What you’ll do

In short: drop in, ship something useful, move on. Two-week sprints, each in a different corner of the business.

Picture a Monday two months from now. You’re embedded with our legal team for the fortnight - shadowing a contract review, working out where the friction is, building a working AI thing that saves a lawyer hours, evaluating it properly, and handing it over so it keeps running when you leave. Two weeks later you’re with marketing on a different problem entirely. Three weeks after that, customer support. Then research. Then recruitment.

So in any given sprint you’re:

• Walking into a corner of the business that hasn’t cracked AI yet, and spotting the agentic opportunity in things people don’t even think of as a process
• Sitting alongside the people closest to the work and learning, fast, how they actually operate
• Designing, building and shipping a real thing - not a deck, not a strategy, an artefact someone uses on Monday morning
• Evaluating it properly: did this actually help, by how much, against what
• Helping the team adopt what works - then disappearing to the next domain entirely
• Building a sharp, opinionated take on which AI tools are actually best for what, and sharing it back across the org

Background - open

We’re open on seniority. You could be early in your career or you could have run large teams. The only non-negotiable is that you’re still hands‑on yourself - building, not delegating, not strategising from a distance. If “hands‑on” has drifted away from your day job, this isn’t the role for you.

You don’t need a security background, and you don’t need to have followed a conventional route into AI. You could come from product, operations, research, engineering, design, marketing, consulting, or somewhere less obvious. We care more about what you’ve built, how you think, and how you work with others than about a particular title or career path.

Why this role is different

Most “AI transformation” jobs are strategy roles at a distance - frameworks, slides, steering committees. This isn’t that. This is the role for the person who actually wants to do the transforming.

PortSwigger is serious about AI, has the budget and the mandate to move fast, and is looking for a small number of people who want to be inside the work.

Salary

We pay excellent salaries above the normal market level, determined by individual skills and contribution. For this role we expect to offer starting salaries in the range of £80,000 to £150,000.

You’ll also receive share options, an 8% employer pension contribution, life assurance (4× salary), income protection, private medical insurance (Bupa), and 25 days holiday plus public holidays.

Why Join PortSwigger?

At PortSwigger, we are a team of passionate individuals who believe in creating extraordinary outcomes for our customers and colleagues. Our culture is our superpower—we prioritize trust, autonomy, and continuous learning.

• We provide a high-autonomy, high-trust environment where you can drive your own professional and personal development.
• You’ll have the opportunity to work with a best-in-class product and directly impact customers’ success.
• We foster a collaborative and inclusive workplace, where ideas and innovation thrive.
• Learn more about what makes PortSwimmer unique through our blog, LinkedIn company page, and .Twitter

Join us and help secure the web—one customer at a time