Director of Finance
ABOUT THE ROLE:
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.
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. 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.
WHAT YOU’LL DO:
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.
WHO YOU ARE:
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.
EXTRA CREDIT:
Experience within the healthcare technology industry or Pharmacy Benefit Management space.
Exposure to M&A or post-acquisition integration.
Prior experience at a Series C through E venture-backed startup.
COMPENSATION: $175,000 - $200,000 annually, in addition to bonus and equity
Compensation offered will be determined by geographic location, experience, and qualifications.