Chief of Staff to CEO, Medicare Advantage

Job Description

Serve as a Strategic Advisor: Function as the CEO's trusted strategic advisor, providing key insights and support for critical decisions through comprehensive analysis and pattern recognition across the Medicare Advantage business. Prioritize Ruthlessly: Evaluate and rank strategic initiatives based on their potential impact on growth, quality, and financial performance. Manage the strategic roadmap to ensure company resources are focused on the highest-impact projects. Drive Cross-Functional Execution: Manage complex projects across clinical, operations, finance, and growth teams. Ensure alignment among leaders, establish clear accountability, and streamline execution processes. Build Operating Systems: Design and implement effective management systems, tracking tools, and decision-making processes for the CEO. Create structured reports to highlight risks and opportunities, optimizing information flow and agenda management. Harness AI and Emerging Technology: Discover and implement AI-driven tools to enhance execution, improve decision-making, and increase operational efficiency. Develop innovative solutions to business challenges. Prepare Executive Materials: Develop high-quality presentations and reports for the CEO, Board members, and key stakeholders. Clearly articulate complex information and provide actionable recommendations. Influence Without Authority: Cultivate strong relationships across the organization, driving alignment and accountability through effective communication and collaboration. Navigate Ambiguity: Offer clear direction in uncertain situations, resolve bottlenecks in critical projects, and facilitate constructive alignment when conflicts arise.

Qualifications

1. 10+ years of experience in high-performing settings such as Chief of Staff roles, leading consulting firms (e.g., McKinsey, Bain, BCG), investment firms, high-growth startups, or strategic operations. 2. Experience in building and scaling operating models, turning strategic visions into practical execution plans. 3. Experience with leveraging AI technologies to drive efficiency and innovation. 4. Excellent prioritization skills in dynamic environments, ability to move between strategic thinking and tactical execution. 5. Strong interpersonal and influencing skills, able to build trust and drive results without formal authority. 6. Knowledge of healthcare or Medicare Advantage sector is advantageous.

Benefits

- Competitive base salary and equity opportunities, including a performance-based bonus. - Comprehensive health, dental, and vision coverage. - Focus on mental well-being with No-Meeting Fridays, company holidays, and flexible time-off policy. - Learning programs, mentorship opportunities, and professional development funding. - Employee Stock Purchase Plan (ESPP), remote work culture, and paid parental leave.