VP of Finance

Location: Remote (Florida a plus) About Upside Upside is redefining how housing stability drives health outcomes. Through one integrated platform, Upside partners with health plans, government payers, and employer groups to identify members at risk, develop individualized housing plans, secure placements quickly, and track outcomes over time. By addressing housing as a core social determinant of health, Upside helps reduce avoidable utilization, improve member stability, and deliver measurable ROI. About the Role This is a senior finance leadership role responsible for Upside's financial strategy, operations, and reporting as the company scales its housing-stability platform for health plans, government payers, and employer groups. The VP of Finance will partner closely with the Fractional CFO and executive leadership to build scalable financial infrastructure, strengthen revenue cycle operations, and support Upside's continued growth. Given Upside's payer-based revenue model, deep experience with Revenue Cycle Management (RCM) — including billing, claims, reimbursement, and payer contracts — is required. The ideal candidate brings a healthcare finance background and is comfortable building processes and systems in a fast-paced, evolving environment. This role is remote; candidates based in Florida are a plus. Your Responsibilities Financial Strategy & Leadership Own Upside's financial strategy, planning, and reporting, partnering with the Fractional CFO and executive team on budgeting, forecasting, and long-range planning Build and mature financial infrastructure, systems, and processes to support Upside's growth across health plans, government payers, and employer groups Provide financial analysis and reporting that inform strategic decision-making across the organization Revenue Cycle Management & Payer Operations Own and optimize Revenue Cycle Management (RCM) processes, including billing, claims submission, reimbursement, and payer contract compliance Partner with Client Success and Operations teams to ensure accurate, timely billing and collections across health plan, government payer, and employer group contracts Identify and resolve revenue cycle bottlenecks, denials, and reimbursement delays Ensure financial processes align with payer requirements and healthcare industry regulations Accounting & Compliance Oversee accounting operations, including monthly close, reconciliations, and financial statement accuracy Ensure compliance with GAAP, healthcare industry regulations, and applicable audit requirements Manage relationships with external auditors, tax advisors, and financial partners FP&A & Business Partnering Develop financial models, forecasts, and scenario planning to support company growth and investment decisions Partner with Sales, Operations, and Product leadership to evaluate the financial impact of new contracts, pricing models, and business initiatives Build reporting frameworks that connect financial performance to operational and client outcomes Team & Process Building Build and lead the finance function as Upside scales, including hiring, structuring, and mentoring future team members Establish scalable financial systems, controls, and processes where they do not yet exist Partner with Technology and Data teams to improve financial reporting automation and infrastructure What Success Looks Like Strong Revenue Cycle Performance Billing, claims, and reimbursement processes run efficiently and accurately across all payer types, minimizing denials and days sales outstanding. Scalable Financial Infrastructure Financial systems, controls, and reporting processes scale smoothly as Upside grows across new clients and markets. Trusted Financial Partnership Executive leadership and the Fractional CFO rely on the VP of Finance for accurate, timely financial insight that informs strategic decisions. Compliance & Accuracy Financial statements, audits, and payer-related compliance requirements are consistently accurate and audit-ready. Qualifications 8+ years of progressive finance leadership experience, including experience as a VP of Finance, Controller, or senior finance leader Demonstrated experience with Revenue Cycle Management (RCM), including billing, claims, and payer reimbursement processes — required Background in healthcare, digital health, value-based care, payer environments, or healthcare technology — required Experience partnering with a CFO, executive leadership, or board on financial strategy and reporting Strong technical accounting knowledge, including GAAP and financial statement preparation Experience building financial infrastructure, systems, and processes in a high-growth or evolving environment Exceptional analytical, communication, and cross-functional collaboration skills Based in Florida a plus, though the role is remote