Head of Strategic Finance

Role Description

Our Finance Organization Mission: To serve as a trusted strategic partner that enables sustainable growth and high-quality patient care through rigorous financial stewardship, data-driven insights, and operational excellence.

Your North Star: We are looking for a Head of Strategic Finance. In this leadership role, you will play an integral role in forming Pomelo’s long-term business strategy and ensuring we achieve financial and growth objectives. You will not only own the company’s forecasting and long-term financial strategy, but also architect our go-to-market approach. You will bridge the gap between financial targets and operational reality, ensuring that our revenue engine is efficient, predictable, and scalable.

Your key responsibilities will include:

• Architect Long-Term Financial Strategy and Strategic Vision: Partner with the leadership team to define the 3-5 year strategic vision, translating high-level corporate goals into actionable financial milestones and capital allocation strategies. Proactively identify new strategic finance priorities and growth levers to drive the business forward, acting as a catalyst for change rather than just a reporter of results.
• Strategic Decision Support: Provide financial analysis and insights required to evaluate high-impact decisions and support key strategic initiatives, such as new partnership opportunities, pricing model changes, or major hiring investments.
• Lead Financial Planning: Own the financial forecast and manage the annual budgeting process, headcount planning, quarterly updates, and variance analysis to ensure capital efficiency.
• Define the "Metrics that Matter": Refine and govern the key financial and operational metrics used to monitor business performance, ensuring consistent definitions and "single source of truth" reporting across the company.
• Optimize Business Economics: Partner with key stakeholders to drive strategy and operational decisions that improve key metrics (LTV:CAC, gross margin, OpEx, product-line profitability, conversion rates, net revenue retention) and other key financial metrics.
• Board Reporting: Produce Board-level financial reporting and analyses, including investor-ready narratives that highlight performance drivers and risks.
• Architect the GTM Operating System: Define and manage financial and operational processes required to optimize growth and revenue realization, including funnel definitions, lifecycle logic, handoff rules, pricing governance, and operational SLAs across Growth, Marketing, and Customer Success.
• Sales Forecasting: Accountable for the design of the sales forecasting methodology, including pipeline coverage standards and roll-up logic, to ensure forecasts match financial reality. Partner closely with leadership to diagnose funnel performance, identify friction points, and drive improvements that increase conversion rates and net revenue retention.
• Cross-Functional Thought Partner: Collaborate with key cross-functional partners including the People and Legal teams to develop efficient policies and processes, such as sales compensation plans and reimbursement policies.
• GTM Tech Stack: Partner closely with Growth, Customer Success, Marketing and IT to evolve our GTM technology stack, including the adoption of AI-powered tools and automation solutions to ensure data integrity, enrichment, automation, and seamless integration between CRM and Finance systems.

Who you are

• 10+ years of progressive finance experience, including investment banking, venture capital, PE, or operating finance roles at a tech or healthcare startup
• 5+ years leading high-performing teams
• Advanced capability in analyzing data to generate actionable insights, drive accurate forecasting, and inform strategic decision-making for executive leadership.
• Proficiency with data analysis, reporting, and Business Intelligence tools (e.g., Metabase, Google Sheets/Excel) to translate complex data into actionable insights.
• Success in leading complex, high-impact, cross-functional projects from conception through execution.
• A pragmatic and versatile mindset capable of serving as a strategic advisor to leadership while simultaneously executing and "rolling up your sleeves".
• Excellent attention to detail and strong, collaborative analytical and problem-solving abilities.
• Ability to thrive in a fast-paced, dynamic environment and adapt to changing priorities.
• Experience with annual GTM planning and sales compensation management rhythms.

Why you should join our team

By joining Pomelo, you will get in on the ground floor of a fast-moving, well-funded, and mission-driven startup where you will have a profound impact on the patients we serve. And you'll learn, grow, be challenged, and have fun with your team while doing it.

We strive to create an environment where employees from all backgrounds are respected. We value working across disciplines, moving fast, data-driven decision making, learning, and always putting the patient first. We also offer:

• Competitive healthcare benefits
• Generous equity compensation
• Generous PTO policy

At Pomelo, we are committed to hiring the best team to improve outcomes for all patients, regardless of their background. We need diverse perspectives to reflect the diversity of problems we face and the population we serve. We look to hire people from a variety of backgrounds, including but not limited to race, age, sexual orientation, gender identity and expression, national origin, religion, disability, and veteran status.

Our salary ranges are based on paying competitively for our company’s size and industry, and are one part of the total compensation package that also includes equity, benefits, and other opportunities at Pomelo Care. In accordance with New York City, Colorado, California, and other applicable laws, Pomelo Care is required to provide a reasonable estimate of the compensation range for this role. Individual pay decisions are ultimately based on a number of factors, including qualifications for the role, experience level, skillset, geography, and balancing internal equity. A reasonable estimate of the current salary range is $250,000 - $300,000 annually. We also believe that your personal needs and preferences should be taken into consideration, so we allow some choice between equity and cash.

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