Head of Finance

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 operating models, scenario plans, and unit economics from scratch in a startup environment, and you can defend your assumptions with board-level rigor - You're a hands-on operator: you've closed the books, managed vendors, and run payroll, not just managed people who do those things - You translate complex financial data into clear insights for a non-finance audience and are comfortable presenting to founders, board members, and investors - You have a track record of implementing finance systems and building processes from scratch. You know when the current tool is right-sized and when it's time to graduate, and you don't over-engineer - You've designed or built AI-native workflows for finance tasks, or have a strong instinct for where AI eliminates manual work without adding fragility NICE TO HAVE - You've owned a fundraising process or been the key finance partner in one. You know how to organize a data room, work through diligence questions, and build investor confidence through metrics and narrative - You've managed a transition from outsourced to in-house accounting - You've worked on rev ops, pricing strategy, or sales commission structures alongside core FP&A work JOINING US To start, you'll have a handful of conversations with our team and founders. If there is mutual excitement, we'll invite you to the office where you'll work on a small project and meet the team.