Deal Desk Finance Analyst/Lead

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 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 60+ leading health systems across the country. If you’re excited to help shape the future of healthcare, we’d love to meet you.

About the role
Plenful is seeking a Deal Desk Finance Analyst/Lead to support and scale our go-to-market motion through strong financial analysis, pricing governance, and cross-functional partnership. This role sits within Finance and works closely with Sales, Customer Success, Revenue Operations, Legal, and other stakeholders to ensure commercial activity is financially sound, policy-compliant, and operationally efficient. The ideal candidate brings a strong analytical mindset, attention to detail, and a passion for translating pricing strategy, commercial policies, and financial guardrails into scalable, repeatable GTM processes that enable growth while protecting revenue quality.

• Review and structure sales deals to ensure compliance with pricing, discounting, revenue recognition, and contracting policies, providing guidance that optimizes revenue, mitigates risk, and supports forward deal momentum.
• Support pricing and deal analysis by building and maintaining pricing workbooks and spreadsheets, validating deal economics, evaluating ROI considerations where applicable, and ensuring accuracy across quotes, order forms, and related deal terms for strategic customers.
• Provide end-to-end deal desk support from quote to signature, including quote building, pricing and order form approvals, coordination of non-standard language requests, contract execution, opportunity closure, and ensuring pricing and commercial details are accurately captured across systems.
• Partner cross-functionally with Sales, Customer Success, Finance, Legal, and others  to streamline the deal process, resolve deal blockers, and deliver timely, high-quality support.
• Drive continuous improvement through financial analysis by monitoring go-to-market performance and pricing trends, identifying opportunities to strengthen commercial economics and execution efficiency, and partnering with GTM teams to ensure alignment with financial policies and objectives.

What we’re looking for

• 3–5 years of experience in Commercial Finance, Sales Finance, pricing strategy, deal economics, or a related analytical role supporting go-to-market teams.
• Strong financial and analytical skills, with the ability to evaluate pricing structures, commercial economics, and GTM performance using spreadsheets and data-driven analysis.
• Experience partnering cross-functionally with Sales, GTM Operations, Legal, and Finance to support commercial execution and resolve complex, time-sensitive issues.
• Solid understanding of pricing, discounting, contracting concepts, and revenue recognition considerations within a SaaS or recurring-revenue business.
• High attention to detail and the ability to manage multiple workstreams while maintaining accuracy under tight timelines.
• Clear, confident communicator who can explain financial concepts and tradeoffs to non-finance stakeholders and influence GTM behavior through data and guidance.
• Experience in a tech start-up environment is a plus, especially in healthcare.

• Great benefits include unlimited PTO, health insurance, meal stipend, health & wellness stipend, team offsites, 401K matching, and stock options
• Join an all-star team with direct access to executive leadership
• Opportunities to further develop and refine your partnership acumen by partnering with our seasoned leaders