Head of AI Operations

Job description

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 work…