Chief of Staff to CEO, Medicare Advantage

Clover Health

Chief of Staff to the CEO driving critical initiatives for Clover Health's Medicare Advantage business. Operate with strategy and execute to shape the company’s growth and success.

Posted 6/27/2026full-timeRemote • 🇺🇸 United StatesLead💰 $180,000 - $230,000 per yearWebsite

About the role

Key responsibilities & impact

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.
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.
Build Operating Systems: Establish the rhythms, tracking mechanisms, and decision cadences the CEO needs to run the business effectively.
Harness AI and Emerging Technology: Identify opportunities to deploy AI-powered tools that accelerate execution, improve decision quality, and unlock operational leverage.
Prepare Executive Materials: Create high-quality narratives and presentations for the CEO, Board, and executive stakeholders.
Influence Without Authority: Build trust across the organization. Rally leaders around shared priorities.
Navigate Ambiguity: Provide clarity when the path forward is uncertain and facilitate thoughtful alignment when priorities are in conflict.

Requirements

What you’ll need

You have 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.
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

Comp & perks

Financial Well-Being: Our commitment to attracting and retaining top talent begins with a competitive base salary and equity opportunities. Additionally, we offer a performance-based bonus program, 401k matching, and regular compensation reviews to recognize and reward exceptional contributions.
Physical Well-Being: We prioritize the health and well-being of our employees and their families by providing comprehensive medical, dental, and vision coverage. Your health matters to us, and we invest in ensuring you have access to quality healthcare.
Mental Well-Being: We understand the importance of mental health in fostering productivity and maintaining work-life balance. To support this, we offer initiatives such as No-Meeting Fridays, company holidays, access to mental health resources, and a generous flexible time-off policy.
Professional Development: We are committed to developing our internal talent. We offer learning programs, mentorship, professional development funding, and regular performance feedback and reviews.
Additional Perks: Employee Stock Purchase Plan (ESPP) offering discounted equity opportunities, reimbursement for office setup expenses, monthly cell phone & internet stipend, remote-first culture, enabling collaboration with global teams, paid parental leave for all new parents, and much more!

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

strategic operationsAI deploymentoperating model designprioritizationdecision-makingnarrative creationpresentation skillsaccountability mechanismscross-functional executionsystems thinking

Soft Skills

influence without authorityrelationship buildingtrust buildingclarityadaptabilityproblem-solvingcommunicationstrategic thinkingexecutionambiguity navigation