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. CYBERSECURITY AWARENESS NOTICE In response to ongoing and industry-wide fraudulent recruitment activities (i.e., job scams), Rightway wants to inform potential candidates that we will only contact them from the @rightwayhealthcare.com email domain. We will never ask for bank details or deposits of any kind as a condition of employment. ABOUT RIGHTWAY: Rightway is on a mission to harmonize healthcare for everyone, everywhere. Our products guide patients to the best care and medications by inserting clinicians and pharmacists into a patient’s care journey through a modern, mobile app. Rightway is a front door to healthcare, giving patients the tools they need along with on-demand access to Rightway health guides, human experts that answer their questions and manage the frustrating parts of healthcare for them. Since its founding in 2017, Rightway has raised over $300mm from investors including Khosla Ventures, Thrive Capital, Francisco Partners, and Tiger Global. We’re headquartered in New York City, with satellite offices in Denver and Dallas. Our clients rely on us to transform the healthcare experience, improve outcomes for their teams, and decrease their healthcare costs. HOW WE LIVE OUR VALUES TO OUR TEAMMATES: We’re seeking those with passion for healthcare and relentless devotion to our goal. We need team members that embody our core values: 1) We are human, first Our humanity binds us together. We bring the same empathetic approach to every individual we engage with, whether it be our members, our clients, or each other. We are all worthy of respect and understanding and we engage in our interactions with care and intention. We honor our stories. We listen to—and hear—each other, we celebrate our differences and similarities, we are present for each other, and we strive for mutual understanding. 2) We redefine what is possible We always look beyond the obstacles in front of us to imagine new solutions. We approach our work with inspiration from other industries, other leaders, and other challenges. We use ingenuity and resourcefulness when faced with tough problems. 3) We debate then commit We believe that a spirit of open discourse is part of a healthy culture. We understand and appreciate different perspectives and we challenge our assumptions. When working toward a decision or a new solution, we actively listen to one another, approach it with a “yes, and” mentality, and assume positive intent. Once a decision is made, we align and champion it as one team. 4) We cultivate grit Changing healthcare doesn’t happen overnight. We reflect and learn from challenges and approach the future with a determination to strive for better. In the face of daunting situations, we value persistence. We embrace failure as a stepping stone to future success. On this journey, we seek to act with guts, resilience, initiative, and tenacity. 5) We seek to delight Healthcare is complicated and personal. We work tirelessly to meet the goals of our clients while also delivering the best experience to our members. We recognize that no matter the role or team, we each play a crucial part in our members’ care and take that responsibility seriously. When faced with an obstacle, we are kind, respectful, and solution-oriented in our approach. We hold ourselves accountable to our clients and our members’ success. Rightway is proud to be an Equal Opportunity Employer that believes in the strength of diverse thought, beliefs, backgrounds, and education. We foster an inclusive culture where differences are celebrated to drive the best business decisions possible. We do not discriminate on any basis protected by applicable law. All employment decisions are based on merit, qualifications, need, and performance.

Director of Finance

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