VP, Finance

About Plenful

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 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 100+ leading health systems, pharmacies, and healthcare organizations 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.

We're looking for a VP of Finance to run strategic finance and accounting at Plenful. Reporting to the CEO, you'll own the operating plan, the forecast, and the economics behind every major resourcing decision the leadership team makes.

This is a hands-on role at a company that is scaling quickly. You'll inherit a current, well-run accounting function and an AI-driven finance stack that's already in place. Your job is to take both further.

What you'll do

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

Own capital allocation. Bring a recommendation, not a menu. Where each million $ is invested, what it has to return, and what we stop doing.

Own the economics. Unit economics, S&M and R&D investments, gross margin by product, and the pricing and deal structures that move them.

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

Own leadership and board reporting. Weekly, monthly and quarterly metrics leadership runs on.

Build the decision layer. Our core systems are already in place. Mature the processes and strategic decision making running on top of them.

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

What we're looking for

8+ years in finance, including running finance or FP&A at a high-growth AI B2B SaaS company through Series B scale and beyond.

A track record of taking a high functioning finance team to the next level of rigor: sharper forecasting, active 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.

Proven transaction experience required. Supporting a financing round, an acquisition, an IPO, or a similar diligence process from the finance leadership seat.

A sharp business partner. You’re 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

Why You'll Love Working Here

🚀 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

Benefits & Perks

🏥 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