Chief of Staff

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About the role

Our Mission 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. Your Mission 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. Things you'll be working on • 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. You will love this role if you have/are… • 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. Why join us? 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,

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