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jobgether

Chief of Staff to CEO, Medicare Advantage

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This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Chief of Staff to CEO, Medicare Advantage based in the United States.

This is a high-impact, executive-level operating role supporting the CEO of a rapidly scaling Medicare Advantage business. You will act as a trusted extension of the CEO, driving clarity across strategy, execution, and organizational priorities in a complex, fast-moving healthcare environment. The role blends strategic thinking with hands-on execution, requiring someone who can turn ambiguity into structured decisions and measurable outcomes. You will operate across clinical, finance, operations, and growth teams, ensuring alignment and accelerating execution at scale. This position is designed for a builder who thrives in environments without predefined playbooks and knows how to create structure where none exists. You will also help shape operating systems, decision-making rhythms, and cross-functional execution frameworks that enable the business to scale efficiently. This is a rare opportunity to directly influence the trajectory of a mission-driven healthcare organization.

Accountabilities:

  • Serve as a strategic proxy to the CEO, representing leadership in high-stakes discussions and supporting critical decision-making through structured analysis and clear recommendations
  • Drive prioritization across the Medicare Advantage organization, ensuring focus is aligned to growth, quality, and financial objectives
  • Lead cross-functional execution of strategic initiatives spanning clinical, operations, finance, and growth teams, ensuring accountability and delivery
  • Design and implement operating systems, including executive rhythms, reporting structures, and decision cadences to improve organizational efficiency
  • Identify opportunities to leverage AI and emerging technologies to streamline workflows, enhance decision-making, and improve execution speed
  • Prepare executive-level materials, including board updates, strategy documents, and performance narratives that simplify complex information
  • Resolve ambiguity across teams by clarifying ownership, aligning stakeholders, and unblocking stalled initiatives
  • Establish tracking mechanisms and performance frameworks that improve visibility into business outcomes and execution progress

    • Requirements:

    • 10+ years of experience in high-growth environments such as startups, scale-ups, consulting, or strategic operations roles with end-to-end ownership of outcomes
    • Proven experience acting as Chief of Staff, strategic operator, or equivalent senior cross-functional leadership role
    • Demonstrated ability to operate in ambiguity, build structure from scratch, and translate strategy into execution
    • Strong track record of influencing senior stakeholders and operating effectively without formal authority
    • High fluency in AI tools and a proven ability to deploy AI to improve workflows, decision-making, or operational efficiency
    • Strong systems thinking with the ability to design scalable processes and operating models
    • Exceptional communication skills, with the ability to simplify complexity and influence executive audiences
    • Strong prioritization skills and sound judgment under pressure in fast-changing environments
    • Healthcare or Medicare Advantage experience is a plus but not required; adaptability and rapid learning ability are essential

      • Benefits:

      • Competitive base salary ranging from $180,000 – $230,000 USD
      • Equity opportunities and performance-based bonus structure
      • Comprehensive medical, dental, and vision insurance
      • 401(k) retirement savings plan with company match
      • Flexible remote-first work environment
      • Generous flexible PTO and company holidays
      • Paid parental leave for all new parents
      • Mental health support and wellness resources
      • Employee stock purchase program and additional financial wellness benefits
      • Reimbursement for home office setup and monthly connectivity stipend
      • Professional development and learning support programs
      • High-impact executive exposure with direct influence on company strategy.
How Jobgether works:
We use an AI-powered matching process to ensure your application is reviewed quickly, objectively, and fairly against the role's core requirements. Our system identifies the top-fitting candidates, and this shortlist is then shared directly with the hiring company. The final decision and next steps (interviews, assessments) are managed by their internal team.
We appreciate your interest and wish you the best!
Data Privacy Notice: By submitting your application, you acknowledge that Jobgether will process your personal data to evaluate your candidacy and share relevant information with the hiring employer. This processing is based on legitimate interest and pre-contractual measures under applicable data protection laws (including GDPR). You may exercise your rights (access, rectification, erasure, objection) at any time.
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