Sidecar Health is redefining health insurance. Our mission is to make excellent healthcare affordable and attainable for everyone. We know that to accomplish this lofty mission, we need driven people who will make things happen. The passionate people who make up Sidecar Health's team come from all over, with backgrounds as tech leaders, policy makers, healthcare professionals, and beyond. And they all have one thing in common—the desire to fix a broken system and make it more personalized, affordable, and transparent. If you want to use your talents to transform healthcare in the United States, come join us! About the Role

As the Director of Financial Planning, Reporting, & Analysis, you'll be a strategic leader driving Sidecar Health's financial insight and operational discipline. Reporting to the Vice President of Finance, you will own critical planning, forecasting, and analysis efforts that inform executive decision-making across the business. You'll partner closely with senior leadership to translate strategy into actionable financial plans, design scalable reporting infrastructure, and identify opportunities to optimize performance. This role requires a blend of strategic vision and hands-on execution - you'll build complex models, synthesize data into compelling narratives, and influence executives at the highest levels. Your work will be central in guiding the company through growth milestones, supporting capital planning, and ensuring Sidecar Health has the financial clarity and agility to deliver on its mission. What You'll Do Lead all FP&A operations, including annual budgeting, monthly/quarterly forecasting, long-term planning, and financial modeling Partner with the VP of Finance, Controller, and executive leaders to translate strategic priorities into measurable financial outcomes Build and scale reporting tools, dashboards, and processes that deliver timely, accurate insights to executives and the board Own variance analysis and key performance metrics, surfacing trends and driving actionable recommendations Support IPO readiness by developing financial models, preparing audit materials, and contributing to S-1 filings and investor presentations Evaluate and advise on business cases, capital investments, and cost optimization initiatives in collaboration with cross-functional teams Drive scenario planning to anticipate business needs, assess risks, and inform executive decision-making Ensure all financial models, forecasts, and reports adhere to GAAP and internal controls Champion process improvements to improve forecasting accuracy, shorten reporting cycles, and strengthen decision-making Mentor, develop, and scale the FP&A team, fostering analytical excellence and strong business partnership Partner with Finance Systems and IT to enhance automation, data quality, and integration across platforms Lead preparation of board and investor materials, providing clear, insightful financial narratives What You'll Bring Bachelor's degree in Finance, Accounting, or related field (MBA or advanced degree a strong plus) 8+ years of FP&A experience, including leadership experience, ideally in high-growth tech, healthtech, or insurance Proven track record of leading budgeting, forecasting, and long-range planning processes Expert in financial modeling, variance analysis, and business case development Hands-on experience with financial systems (NetSuite or equivalent) Advanced Excel skills and proficiency in building scalable reporting Strong communication and executive presence, with the ability to influence and partner across the C-suite and board What You'll Get Competitive salary, bonus opportunity, and equity package Comprehensive Medical, Dental, and Vision benefits A 401k retirement plan Paid vacation and company holidays Opportunity to make an impact at a rapidly growing mission-driven company transforming healthcare in the U.S. Sidecar Health is an Equal Opportunity employer committed to building a diverse team. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status or disability status.