HeadofFinance

Our mission is to help small businesses run themselves. We’re starting with doctors’ offices, building autonomous systems that handle busywork and complete the workflows that keep the office moving every day. Our team is small, flat, and ambitious. We value craft, intellectual rigor, and direct communication. ABOUT THE ROLE As Lassie's first finance hire, you'll build out the company's financial operations from the ground up. You'll work alongside CEO Steijn Pelle and Lassie advisor Jason Warnick (former CFO, Robinhood). You'll own the transition from founder-led finance to a world-class, AI-native function. This is a unique opportunity to build the systems that shape how Lassie grows and operates. This role is as strategic as it is operational. You'll be involved in every major financial decision, from daily tradeoffs to strategic finance projects, and you'll be the person who gives the leadership team confidence in where the company stands and where it's headed financially. WHAT YOU'LL DO - Establish and own the reporting of the company's key metrics (think active practices, ACV, ARR, net dollar retention, churn, payback period) so you can measure progress - Build and maintain the company's financial operating model, including scenario planning and tradeoff visibility, so leadership can make confident resource and growth decisions - Ensure an accurate, timely monthly close and deliver financial statements that give leadership an actionable view of the business - Own the full FP&A cycle: budget, quarterly actuals, monthly reporting - Serve as the CEO's key finance partner through future fundraises - Build scalable, AI-native finance infrastructure across accounting, forecasting, spend management, and payroll, choosing tools that reduce complexity and grow with the company without overbuilding - Lead strategic finance work beyond the core: pricing structure, sales commission design, rev ops foundations, and more WHAT WE'RE LOOKING FOR MUST-HAVE - You've built operat