Chief of Staff

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

Our mission is clear: we're here to create a world where everything operates at its very best, ensuring that every employee receives the support they need to live life to the fullest, both at work and beyond.

Ben has more business-critical bets than it has people who can own one. As our Chief of Staff, you will take the hardest and most ambiguous of them and turn them into shipped outcomes: new propositions, incubation bets, structural changes to how the company runs. When something matters and there's no obvious owner or playbook, it lands with you.

This is not your typical Chief of Staff role - it is a true builder's role. You'll run point on the cross-functional initiatives that decide where Ben goes next, in close partnership with the founders and with a real hand in shaping the company's next chapter. Ultimately, you’ll have huge agency to drive impact across the whole business.

One Honest Note

We won't pretend this is going to be easy. It's an intense role, and there'll be stretches that properly test you. But get it right, and it's the kind of experience that shapes a career — genuinely some of the most exciting, highest-impact work you'll ever do.

• Own the grey space: take on our most ambiguous, highest-stakes cross-functional projects, the ones with no clear approach, and drive them from a blank page to a delivered result.

• Get our next big bets off the ground: new propositions, incubation, and the strategic projects that don't sit inside any one team's remit. You scope them, you build them, you deliver them.

• You'll own what used to take a team: use Claude, Cursor and similar tools to get through the research, the reporting and the busywork that used to need several people. AI tooling is already a big part of how this team works, and will be essential for this role. The bar is that you're already building with it.

• Win the room: write the narratives that go to the board, the all-hands and the wider company when a project needs buy-in or explaining.

• Build for scale: put in place the light-touch systems and workflows that let 90 people operate like 300, without adding process for its own sake.

• Worked directly with founders: whether that came from strategy, consulting, banking, product, operations, or a Chief of Staff seat before. You know how to give a leadership team real headroom.

• Owned a problem from a blank page through to delivery: with no one else's roadmap to fall back on.

• Real range across strategy and execution: you'll build the model and write the board narrative, then go and do the unglamorous work that makes it happen.

• A background where "no" wasn't the end of it: you've got a plan over the line that other people had written off.

• A first-principles thinker: you work the answer out from scratch. Where you've inherited a playbook, you can tell us what you kept and what you binned.

• Known to follow-through until it's actually done: you chase, you follow up, and you don't let a stalled project quietly die.

• Scaled a fast-growing B2B SaaS business: not essential, but it will put you ahead. You know what breaks at each stage, and what to put in place before it does.

• Genuine hands-on AI experience: you use Claude, Cursor or ChatGPT and have experience building agents/ agentic workflows.

This is a chance to take on the largest, most complex problems in the business, owning them end to end, with the budget, the autonomy to make the calls, and a direct line to the Founders. You'll work across every part of Ben, which means you'll see how the whole company fits together in a way almost nobody else does. When something matters significantly at Ben, you'll most certainly be involved.

Do this role well, and the next step is into our leadership team, potentially running a function, or a major part of the business.

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

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 [email protected].