Director of Finance, Rightway

• This position is ideal for a strategic thinker and hands-on operator who can move fluidly between building an investor-grade financial model and partnering with department leaders on the decisions behind it
• The ideal candidate brings finance leadership experience within the PBM and/or healthcare industry, is a strong communicator, and has exceptional attention to detail
• Bachelor's degree in Finance, Accounting, Economics, or a related field required; MBA or CPA preferred
• 10+ years of progressive experience in FP&A, corporate finance, or investment banking, including finance leadership at a growth-stage tech or healthcare company
• Expert in building dynamic, integrated 3-statement financial models that provide clarity, accuracy, and insight into business performance
• Strong quantitative and problem-solving abilities with a deep understanding of SaaS and healthcare business models (e.g., NRR, CARR, gross margin)
• Experience supporting or preparing for a fundraise or due diligence process
• Proficiency with NetSuite, Salesforce, Excel, and Google Sheets; familiarity with modern financial planning tools is a plus
• Able to translate complex financial concepts into clear, actionable insights for business and technical stakeholders
• Excited by ambiguity and motivated to design and implement scalable processes in a fast-paced, mission-driven environment
• Strong analytical skills, attention to detail, and a methodical approach to troubleshooting and problem solving

Desirable

• Rightway is seeking a Director of Finance to join our growing team. In this role, you will lead our FP&A and strategic finance function and serve as a key partner to Accounting, senior leadership, and the board. You will own the models and numbers that leadership and investors rely on, and shape the strategy behind them
• You will join a lean, high-performing team of technology and healthcare experts who share a mission to humanize the healthcare experience
• This role reports to the SVP of Finance
• Build, own, and continuously improve a dynamic, integrated 3-statement financial model (P&L, balance sheet, and cash flow) that serves as the analytical backbone for planning, scenario analysis, and fundraising
• Lead annual budgeting, monthly and quarterly forecasting, and long-range financial planning across all business functions
• Own cash forecasting including near-term (13-week) and full-year models tied to budget and growth assumptions
• Build runway and scenario models that layer hiring plans and churn to inform strategic decisions
• Prepare board decks, investor reporting, and diligence-ready materials
• Own key SaaS and healthcare metrics, including CARR, net revenue retention, and gross margin
• Lead headcount and compensation planning tied to department budgets and the hiring plan
• Partner with department leaders to drive accountability against plan and advise on the financial implications of business decisions
• Partner with Accounting during monthly close cycles to ensure accurate variance analysis and timely reporting
• Mentor and develop members of the finance team