Director of Finance

DIRECTOR OF FINANCE New York City · On-site THE VOICE AI WORKFORCE FOR HEALTHCARE Healthcare runs on phone calls and loses $450B a year to the administration around them. Patients wait on hold, staff spend hours calling insurers, and revenue leaks at every handoff. At Prosper, we're building the AI workforce that runs healthcare operations end to end. Our voice AI agents answer patient calls, schedule appointments directly in the EHR, verify insurance benefits, automate billing, and get payors on the phone when humans would otherwise wait on hold. We've grown revenue 5x in the last year, partnered with 100+ healthcare organizations covering more than 150,000 providers, and raised $35M, including a $30M Series A led by Andreessen Horowitz. THE ROLE We're hiring a Director of Finance, our first finance hire, to own Prosper's numbers end to end: planning, metrics, reporting, and the finance operations underneath them. Think of it as building a function rather than filling a seat. You'll own both sides of finance: the strategic side (planning, metrics, reporting) and the operational side (accounting, monthly close, payroll and taxes), run with an outsourced partner you manage. Prosper is at an inflection point. Revenue is up 5x in the last year, and finance has to scale with it. It's early enough that the finance playbook is yours to write, and consequential enough that writing it well changes the trajectory of the company. If you've spent years building models and advising on other companies' numbers, this is the version where you own the plan, run the function, and see the business move. WHAT YOU'LL DO Own strategic finance - Build the operating model from a blank page: annual plan, budget, monthly forecast, and the drivers behind each of them - Own the metrics the company runs on: ARR bridge (new logo, expansion, contraction, churn), contracted vs. live ARR, time to go-live, gross margin, burn, and runway - Prepare the monthly investor updates - Keep gross margin accurate, with COGS and vendor costs, including voice AI infrastructure, categorized right every month Run finance operations - Run a fast, accurate monthly close with an accounting partner you choose and manage - Own payroll, taxes, and filings - Get invoices out on time and cash collected on schedule - Set up spend controls: department budgets, expense policies, and a weekly AP and approval process, so the founders stop approving every expense WHAT WE'RE LOOKING FOR - 4-6 years of experience, ideally starting in investment banking and followed by finance at a high-growth startup. - Rigor as a core competency. People trust your numbers because they never have to check them twice - Builder mentality. You're comfortable being the only finance person at first and getting deep into the details of a close, and just as comfortable stepping back to tell the founders what the numbers mean. BONUS POINTS - Healthcare or health tech exposure, at a company or covering the sector in banking - Hands-on with modern finance tools like Brex, Carta, NetSuite or QuickBooks - You've supported a fundraise, a first audit, or a finance system rollout - You've managed an outsourced accounting firm and held it to a high bar WHY PROSPER - A trillion-dollar problem, real customers, and revenue growing 5x - A function you own outright: the plan, the metrics, and the team you build - Direct access to the founders and the board - Competitive base and meaningful equity