Chief of Staff to CEO, Medicare Advantage at Jobgether – United States
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About This Position
This position is posted by Jobgether on behalf of a partner company. We are currently looking for a Chief of Staff to CEO, Medicare Advantage in United States.
This high-impact executive support role is designed for a strategic operator who can serve as a trusted extension of the CEO within a fast-scaling Medicare Advantage business. You will operate at the intersection of strategy, execution, and organizational alignment, helping translate complex priorities into clear, actionable plans. The role requires exceptional judgment to prioritize initiatives, remove roadblocks, and ensure leadership focus remains on the highest-value opportunities. You will work across clinical, operational, financial, and growth functions, acting as a central integrator for cross-functional execution. In a highly dynamic and data-driven environment, you will help design the operating systems that enable scale, speed, and accountability. This is a mission-critical position for a builder who thrives in ambiguity and wants to directly shape business outcomes at the executive level.
- Serve as a strategic proxy to the CEO by supporting high-stakes decisions through structured analysis, first-principles thinking, and synthesis of complex business inputs.
- Drive prioritization across strategic initiatives, ensuring focus is aligned with growth, quality, and financial performance objectives.
- Lead and coordinate cross-functional execution across clinical, operations, finance, and growth teams, ensuring accountability and clarity of ownership.
- Design and implement operating rhythms, reporting cadences, and executive-level dashboards to improve decision-making speed and quality.
- Prepare high-impact executive materials, including board presentations, strategic memos, and leadership updates that translate complexity into clear recommendations.
- Identify and deploy AI-enabled tools and automation opportunities to improve efficiency, execution speed, and organizational leverage.
- Act as a central connector across leadership teams, influencing without authority to align priorities and resolve execution bottlenecks.
- Support enterprise-wide initiatives by providing structure, driving alignment, and ensuring timely delivery of critical programs.
Requirements:
- 10+ years of experience in high-performance environments such as management consulting (McKinsey, Bain, BCG or equivalent), strategy, operations, investing, or startup leadership roles.
- Proven experience operating in Chief of Staff, strategic operations, or executive-facing roles supporting senior leadership.
- Strong ability to structure ambiguous problems, prioritize effectively, and translate strategy into execution plans.
- Demonstrated experience leading cross-functional initiatives in complex, fast-paced, matrixed environments.
- Exceptional analytical skills with the ability to synthesize data into clear insights and executive-level recommendations.
- Strong communication and storytelling abilities, particularly in building executive and board-level materials.
- High emotional intelligence with the ability to build trust and influence stakeholders without formal authority.
- Strong interest or experience in leveraging AI tools to improve productivity and decision-making is highly valued.
Benefits:
- Competitive base salary ranging from $150,000 to $195,000 annually.
- Performance-based bonus eligibility and equity participation opportunities.
- 401(k) retirement savings plan with company match.
- Comprehensive healthcare coverage including medical, dental, and vision insurance.
- Flexible remote-first work environment with home office support.
- Generous paid time off, including holidays, parental leave, and mental health-focused time-off policies.
- Professional development programs, mentorship opportunities, and learning support.
- Additional employee perks including internet stipend, wellness resources, and stock purchase plan.