Chief of Staff to CFO

Swooped is a Talent Platform (not a staffing agency). We are not the employer for this role and do not make hiring decisions. Clicking "Apply" takes you to Swooped to review the role and hiring company details. About the Opportunity The company is looking for an exceptional Chief of Staff to partner closely with the CFO as a strategic thought partner, execution leader, and force multiplier across the organization. This is a highly consequential role at the center of the organization's financial and operating agenda. This is a high-leverage operating role for someone who thrives at the intersection of strategy and execution. You'll extend the CFO's reach by driving critical cross-functional initiatives, translating ambiguity into action, and ensuring leaders are aligned on the decisions and actions that matter most. You'll move fluidly between strategy and execution, frame complex problems quickly, and hold teams accountable for results. The ideal candidate combines strong business judgment, structured thinking, and analytical rigor with low-ego leadership. This role is designed for builders and systems thinkers who bring both strategic vision and operational instinct. You're credible with senior executives, effective across functions, and relentlessly focused on outcomes over activity. Key Responsibilities Extend the CFO's Leverage: Shape priorities, operating rhythms, and decision-making across Finance and the broader organization. Translate high-level goals into concrete execution plans with clear owners, timelines, and decision points. Act as a trusted thought partner by structuring problems, clarifying tradeoffs, and surfacing data-driven recommendations. Lead High-Priority Initiatives: Independently drive the CFO's highest-priority initiatives that cut across finance, actuarial, operations, and product. Lead complex, ambiguous projects from definition through execution. Build action-oriented plans that focus teams on what matters most and translate strategy into measurable outcomes. Strengthen Finance Operating Model: Partner with Finance, Actuarial, and Data teams to evolve finance into a more forward-looking, action-oriented function. Improve how key metrics are defined, tracked, and used to drive decisions. Ensure insights translate into decisions, behavior change, and accountability. Drive Executive Communication: Prepare high-quality materials for Board, Audit Committee, investors, and executive leadership. Craft clear, analytically rigorous narratives around performance, strategic priorities, and risks. Review and refine presentations to ensure clarity and precision before they reach the CFO. Improve Cross-Functional Alignment: Build relationships across finance, actuarial, operations, and product to drive collaboration. Identify misalignment early, force clarity, and resolve cross-functional issues before they become execution problems. Influence senior stakeholders without formal authority. Elevate Decision Quality: Apply first-principles and data-driven thinking to help leadership solve difficult problems. Distill complex issues into decision-ready frameworks. Know when rigor matters most, when to go deep, and when speed trumps perfection. Harness AI and Emerging Technology: Identify opportunities to deploy AI-powered tools that accelerate execution, improve decision quality, and unlock operational leverage. Build solutions, don't wait for permission. Success in this role looks like: First 90 days: Build trust with the CFO and key cross-functional leaders. Establish a clear operating framework for tracking and advancing priorities. Drive critical initiatives with visible traction and accountability. First 6 months: Independently lead multiple high-priority initiatives with measurable progress. Build strong relationships across leadership and be viewed as a trusted, high-judgment partner. Improve quality of executive materials and cross-functional execution. First year: Play a meaningful role in shaping and executing the organization's strategic and financial agenda. Help finance become a more effective driver of business performance. Serve as a critical multiplier for the CFO and trusted leader at the center of the business. Required Qualifications 7–10+ years of experience in consulting, finance, strategy, business operations, investing, healthcare strategy, or other highly demanding operating environments. A builder and systems thinker who breaks down ambiguous problems quickly, creates clarity proactively, and stays accountable for results. Strong business judgment and excels at executive communication. Balances strategy and execution, writes and speaks with precision, and engages credibly with senior leaders. Influences without authority and is analytically rigorous. Comfortable with data, financials, and business metrics to support recommendations. High EQ and low ego: direct, thoughtful, adaptable, and willing to do whatever is needed to help the team win. AI-fluent: has deployed AI to accelerate execution and unlock leverage, and sees opportunities others miss. Healthcare experience is strongly preferred; experience in Medicare Advantage, value-based care, insurance, or related sectors is a significant plus. Bachelor's degree required; MBA or advanced degree is a plus. Benefits Overview Financial Well-Being: Commitment to attracting and retaining top talent begins with a competitive base salary and equity opportunities. Additionally, a performance-based bonus program, 401k matching, and regular compensation reviews are offered to recognize and reward exceptional contributions. Physical Well-Being: Prioritizes the health and well-being of employees and their families by providing comprehensive medical, dental, and vision coverage. Investment is made in ensuring access to quality healthcare. Mental Well-Being: Understands the importance of mental health in fostering productivity and maintaining work-life balance. Initiatives include No-Meeting Fridays, monthly company holidays, access to mental health resources, and a generous flexible time-off policy. A remote-first culture embraces collaboration and flexibility, allowing team members to thrive from any location. Professional Development: Developing internal talent is a priority. Learning programs, mentorship, professional development funding, and regular performance feedback and reviews are offered. Additional Perks: Employee Stock Purchase Plan (ESPP) offering discounted equity opportunities Reimbursement for office setup expenses Monthly cell phone & internet stipend Remote-first culture, enabling collaboration with global teams Paid parental leave for all new parents And much more! About the Organization The organization is reinventing health insurance by combining the power of data with human empathy to keep members healthier. It believes the healthcare system is broken and has created custom software and analytics to empower its clinical staff to intervene and provide personalized care to those who need it most. Members are always put first, and success is measured by the quality of life of the people served. Those who work at the organization are passionate and mission-driven individuals with diverse areas of expertise, working together to solve the most complicated problem in the world: healthcare. From the organization's inception, Diversity & Inclusion have always been key to its success. It is an Equal Opportunity Employer and its employees are people with different strengths, experiences, perspectives, opinions, and backgrounds, who share a passion for improving people's lives. Diversity not only includes race and gender identity, but also age, disability status, veteran status, sexual orientation, religion and many other parts of one’s identity. All employee points of view are key to success, and inclusion is everyone's responsibility. Final pay is based on several factors including but not limited to internal equity, market data, and the applicant’s education, work experience, certifications, etc. A reasonable estimate of the base salary range for this role is: $180,000—$230,000 USD