Chief of Staff to CEO, Medicare Advantage

About the role

The MA CEO is seeking a Chief of Staff to act as a trusted proxy, ruthlessly prioritize across competing initiatives, and build the operating systems required to execute at scale. This is a high-leverage operating role for someone who thrives at the intersection of strategy and execution.

Responsibilities

• Act as the CEO's trusted proxy — not just an advisor, but someone who can represent her in high-stakes rooms and make decisions on her behalf.
• Communicate with clarity and support high-stakes decisions through rigorous analysis, first-principles thinking, and pattern recognition across the business.
• Force-rank initiatives against growth, quality, and financial objectives. Own the strategic roadmap and ensure the organization focuses on work that moves the business.
• Orchestrate complex initiatives across clinical, operations, finance, and growth. Align leaders around clear decisions. Build accountability mechanisms that stick.
• When execution is fragmented, consolidate it. When ownership is unclear, define it.
• Establish the rhythms, tracking mechanisms, and decision cadences the CEO needs to run the business effectively. Design structured updates that surface risks and tradeoffs. Optimize time, agenda, and information flow.
• 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.
• Create high-quality narratives and presentations for the CEO, Board, and executive stakeholders. Translate complexity into clarity. Make recommendations, not just summaries.
• Influence without authority: build trust across the organization. Rally leaders around shared priorities. Drive accountability through clarity and momentum, not escalation.
• Navigate ambiguity: provide clarity when the path forward is uncertain, help unblock critical initiatives that have stalled, and facilitate thoughtful alignment when priorities are in conflict.

Requirements

• 10+ years in high-growth, fast-moving environments — startup or scale-up leadership, strategic operations, or similar high-judgment tracks where you owned outcomes, not just programs.
• You're a builder and systems thinker: you create structure from ambiguity, design operating models that scale, and turn strategy into execution that sticks.
• You're AI-fluent: you've deployed AI to accelerate execution and unlock leverage, and you see opportunities others miss.
• You excel at rapid prioritization in ambiguous environments, move seamlessly from strategy to execution, and know when to push and when to let go.
• You're exceptional at building relationships and influencing across functions without formal authority. You earn trust through clarity, quality, and velocity — not positional power.

Qualifications

• Healthcare or Medicare Advantage experience is a plus but not required. Aptitude and willingness to learn quickly is essential.
• We've seen strong CoS operators come from consulting, tech, finance, and other industries.

Benefits

Financial Well-Being: Competitive base salary and equity opportunities, performance-based bonus program, 401k matching, and regular compensation reviews.

Physical Well-Being: Comprehensive medical, dental, and vision coverage.

Mental Well-Being: No-Meeting Fridays, company holidays, access to mental health resources, and a generous flexible time-off policy.

Professional Development: Learning programs, mentorship, professional development funding, and regular performance feedback and reviews.

Additional Perks: Employee Stock Purchase Plan (ESPP), reimbursement for office setup expenses, monthly cell phone & internet stipend, remote-first culture, paid parental leave for all new parents, and much more!

Pay

A reasonable estimate of the base salary range for this role is: $180,000—$230,000 USD

Schedule

Remote-first culture, enabling collaboration with global teams.

Paid parental leave for all new parents.