VP, Finance

Plenful is on a mission to transform healthcare operations from the inside out. Fresh off our $50M Series B and backed by Notable Capital, Bessemer Venture Partners, TQ Ventures, Susa/Kivu Ventures, and other leading investors, we’re building the category-defining AI workflow automation platform that healthcare teams rely on to operate smarter, faster, and more efficiently. Our technology empowers healthcare operators across hospital and health systems, pharmacies and payors to eliminate manual work, reduce administrative burden, and improve compliance, all while unlocking critical revenue to fund programs for their in-need patient populations.

Built by healthcare operators for healthcare operators, Plenful is driven by a deep understanding of the challenges facing today’s care teams. We’re passionate about equipping healthcare workers with world-class tools that deliver real, measurable impact, and we’re proud to serve 90+ leading health systems across the country. If you’re excited to help shape the future of healthcare, we’d love to meet you. Apply now to join our growing team.

• Own the plan. Annual operating plan and rolling forecast, built on multi-scenario revenue and headcount models leadership actually uses to commit to hires and investments.

• Own capital allocation. Bring a recommendation, not a menu. Where the next $1M goes, what it has to return, and what we stop doing to fund it.

• Own the economics. Unit economics, CAC and payback, gross margin by product, and the pricing and deal structures that move them. AI means the model has real complexity — that's the interesting part.

• Own cash and runway. Burn, scenarios, and a clear read on how much time each plan buys us.

• Be the partner leaders actually want in the room. Go-to-market, engineering, and operations leaders should bring you the decision before it's made, not the invoice after.

• Own leadership and board reporting. The monthly numbers and metrics leadership runs on, and the financial narrative in the board package.

• Build the decision layer. Our core systems are already in place. Connect ERP, expense, payroll, and CRM data into one reporting layer everyone trusts, and mature the processes running on top of them.

• Build the team. Lead, coach, and grow the finance and accounting team.

• 8+ years in finance, including running finance or FP&A at a high-growth B2B SaaS company at Series A through Series C scale

• A track record of taking a functioning finance team to the next level of rigor: sharper forecasting, stronger scenario modeling, management reporting leadership relies on

• Player-coach. You build the model yourself and you develop the people who will eventually own it

• Solid technical accounting foundation, including ASC 606 revenue recognition on complex or milestone-based contracts.

• A sharp business partner. You've told a senior leader something they didn't want to hear and kept the relationship

• Comfort with ambiguity, high ownership, low ego

• Healthcare, regulated-industry, or usage-based pricing experience is a plus, not a requirement

• Experience supporting a company exit, financing round, or IPO strongly preferred

• 🚀 Mission-Driven, World-Class Team — Join an exceptional group of professionals aligned around a meaningful mission and committed to making an impact

• 📈 Opportunities for Growth — Strengthen your expertise through collaboration with experienced, high-performing leaders across the organization

• 🏢 Flexible Hybrid Work Environment — We're remote-first, with meaningful office presence in San Francisco and New York. R&D roles follow a hybrid model, with two days per week in our San Francisco office

• 🏥 Healthcare Coverage — Full medical, dental, and vision insurance for you and participation for your family

• 💰 401(k) with Company Match — Plenful matches 50% of your first 3% contributed

• 📊 Equity — Every full-time employee shares in our success

• 🌴 Unlimited PTO — Take the time you need, when you need it

• 🍽️ Daily Lunch Stipend — $100/week to cover your midday meals

• 💪 Wellness Stipend — $100/month to support your health and well-being

• 🚇 Commuter Benefits — $100/month for SF and NYC-based employees

• 👶 Parental Leave — Paid leave to support growing families