Chief of Staff to CEO, Medicare Advantage

Clover Health

2d•$180,000 - $230,000•Remote

About The Position

Clover's Medicare Advantage business is scaling rapidly. The MA CEO needs a Chief of Staff who can operate 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. You'll drive critical cross-functional initiatives, translate ambiguity into action, and establish operating rhythms that improve decision quality and velocity. You'll work across clinical, operations, finance, and growth — aligning leaders, unblocking progress, and ensuring the business delivers. The ideal candidate is a decisive operator who moves fast, communicates crisply, and knows how to get things done in ambiguous, fast-moving environments. This role is designed for builders who default to action — people who create structure from chaos, not people who need structure to operate effectively. You're energized by driving tangible outcomes and leveraging AI to multiply impact. You're comfortable with ambiguity, move with conviction, and know when to escalate and when to execute.

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.
Aptitude and willingness to learn quickly is essential.

Nice To Haves

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

Responsibilities

Serve as Strategic Proxy: 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. You communicate with clarity and and support high-stakes decisions through rigorous analysis, first-principles thinking, and pattern recognition across the business.
Ruthlessly Prioritize: Force-rank initiatives against growth, quality, and financial objectives. Own the strategic roadmap and ensure the organization focuses on work that moves the business.
Drive Cross-Functional Execution: 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.
Build Operating Systems: 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.
Prepare Executive Materials: 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.