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 pe