Head of AI Operations

Our Mission

We're not your average benefits platform – we're the driving force that uplifts people's lives. Our technology connects the entire benefits ecosystem, creating better outcomes for employers, employees, brokers, and providers.

Our mission is clear: to build a world where everything works at its best, ensuring every employee gets the support they need to thrive—both at work and beyond.

Your Mission

As our

Head of AI Operations

, you own Ben's internal applied AI transformation: reinventing how the whole company works, function by function, so the business runs on a new operating system. You'll work directly with the founders, with the backing, budget and authority to make it a reality.

It's a once-in-a-lifetime role. Where most people get one team and a backlog, you get the whole company as your canvas, from customer operations to commercial, finance and people. You find the work that's slow, manual and held together with duct tape, and you rebuild it so it runs itself. Piece by piece, that becomes the way Ben operates.

There's no better place to do it. Ben's whole mission is to make things work at their best, and we already do that in benefits for thousands of companies. Now we're doing it to ourselves, and you're the one who leads it.

Things you'll be working on

Rebuild the company operating system:

partner with customer operations, finance, people and commercial to find what's slow, manual and held together with duct tape, and redesign it so it runs seamlessly.

Reinvent how work happens:

get hands-on with each function to design and stand up the systems that take on whole workflows end to end, then drive them across the company. A new customer going from signed contract to fully live in days, work that eats weeks today. The customer team looking after twice the number of accounts without anything slipping. The kind of leverage that changes what a company our size can do.

Own the Applied AI strategy:

work with the founders to shape where Ben goes next on applied AI, what we change, in what order, and how we know it's working. Engineering owns how AI goes into the product. You own how AI transforms the way we run internally.

Drive adoption and bring people with you:

help every function become genuinely AI-native. Raise the bar for how teams work day to day, so the change sticks and the systems actually get used.

Set the standard and prove it works:

own the standards, guardrails and quality bar for how Ben adopts AI, and put real evals in place so we know a system works before we trust it with live work, and that it keeps working. Keep us on the right side of compliance as agents start touching customer, people and finance data. This is how what ships gets trusted and used, instead of half-finished pilots piling up.

You'll love this role if you have/are...

High-growth B2B SaaS experience, and evidence you've driven this kind of change:

you've operated at pace in a high growth, scaling SaaS business, and you can show how you've shifted the way teams actually work, with the outcomes to back it up.

A strong systems thinker:

you think about the bigger picture, and have owned complex problems that cut across different parts of a business.

Deep, practical AI fluency:

you use tools like Claude, Claude Code and other AI tooling every day. You've got strong, well-formed views on where they create real value and where they don't, and you can turn that into adoption that sticks across a business.

Exec-level influence in a scaling company:

you can carry a room from ICs to the C-suite, challenge leaders well, and turn ambiguity into aligned action.

A bias for getting your hands dirty:

you don't lead change from a distance. You get inside how a function really works, redesign it, and work with teams proactively to drive change. You've built things people assumed needed a whole team, and you can show us what and the why.

A force multiplier:

You create repeatable systems, lift and develop the people around you, and know when to coach, co-build, push or escalate.

Nice to have(s)

Prompt and context engineering:

you have a structured approach to getting the best out of models, and have experience teaching others to do the same.

Have built the guardrails:

you've set the bar for what an internal AI system is trusted to do, and put real evals behind it, so you know it works before it goes near live data.

Why join us?

This is one of the most important hires we'll make at Ben, and one of the rare roles where a single person can change how an entire company works.

A canvas most people never get:

your remit is the whole company, starting with our biggest and most complex operation, how we deliver for customers.

A real mandate:

you work directly with the founders, with the budget, the tools and the backing to take work off entire teams and change how Ben runs.

You'll be at the frontier:

the market hasn't even settled on a name for this role yet. Do it well and you write the playbook everyone else copies in a couple of years.

The most impactful work of your career:

Ben helps hundreds of thousands of people across 30+ countries get the benefits and support they need. Make our functions work better and that reaches every one of them.

Our Compensation & Benefits

It’s important to us to practise what we preach when it comes to our benefits. We know what good looks like and we want to provide the best for our team, with a comprehensive and inclusive benefits package. This means you have a choice over the things that are most important to you. You can see a selection below, along with the full offering

here

.

💰

Competitive base salary

+

equity,

so you own what you build

💳

£100 monthly personal Ben Balance:

for whatever works for you, whether that's Netflix, Spotify, or a really expensive cup of coffee! This allowance will

increase by £50 for each year of service until you reach £250

🍔

Weekly lunch provided in office

so you can spend quality time with the team over some tasty food!

🏖

28 days of holidays

a year plus bank holidays, and an option to

buy or sell 2 days per year

. Also, your holiday entitlement will

increase to 30 days at your 3rd year of service!

🌴 Work-from-abroad scheme,

so you can support your travels, enjoy an extended holiday, or visit loved ones.

🍼 Enhanced parental leave

and

workplace nursery scheme

to support with the cost of childcare in a nursery setting

❤️

Comprehensive

Private Medical Insurance

💌 Funded Life Assurance cover

with the option to voluntarily increase - this also includes an annual health check

Diversity and Culture at Ben

We are organically growing a brilliantly diverse, inclusive and respectful bunch of people we are extremely proud of. This should go without saying but all applications are very much welcome. If you need any adjustments to support you with your application, just let us know by emailing

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