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Plenful is an AI automation platform transforming healthcare operations. Fresh off a $50M Series B, the company serves 100+ leading health systems, pharmacies, and healthcare organizations, helping them eliminate manual work, reduce administrative burden, and improve compliance.
You will report directly to the CEO and own strategic finance and accounting at a rapidly scaling company. This is a hands-on role where you'll inherit a well-run accounting function and an AI-driven finance stack already in place, with the mandate to mature both further.
Key responsibilities:
- Develop and own the annual operating plan and rolling forecast using active multi-scenario models that leadership uses to commit to hires and investments
- Own capital allocation decisions: recommend where each million dollars is invested, what returns are required, and what initiatives to stop
- Drive unit economics, S&M and R&D investment analysis, gross margin by product, and pricing/deal structures
- Partner with go-to-market, product, engineering, and operations leaders as a strategic advisor, bringing finance perspective before decisions are made
- Own all leadership and board reporting (weekly, monthly, quarterly metrics)
- Build and mature the decision-making layer on top of existing core systems, including processes and strategic frameworks
- Lead, coach, and grow the strategic finance and accounting team
The company operates a remote-first model with meaningful office presence in San Francisco and New York. Benefits include full medical/dental/vision coverage, 401(k) with 50% match on first 3%, equity for all full-time employees, unlimited PTO, $100/week lunch stipend, $100/month wellness stipend, commuter benefits, and paid parental leave.
REQUIREMENTS:
- 8+ years in finance, including running finance or FP&A at a high-growth AI B2B SaaS company through Series B scale and beyond
- Track record of taking a high-functioning finance team to the next level: sharper forecasting, active scenario modeling, management reporting that leadership relies on
- Player-coach mentality: you build models yourself and develop people who will eventually own them
- Solid technical accounting foundation, including ASC 606 revenue recognition on complex or milestone-based contracts
- Proven transaction experience required: supporting a financing round, acquisition, IPO, or similar diligence process from the finance leadership seat
- Strong business partner skills: comfortable having hard conversations with other leaders while maintaining strong relationships
- Comfort with ambiguity, high ownership, low ego
- Healthcare, regulated-industry, and AI-native experience is a plus
