Chief of Staff to CEO, Medicare Advantage

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 strategically-minded, principle-oriented leader with exceptional judgment and influence who thrives in fast-paced environments. This role is designed for builders and systems thinkers who bring both strategic vision and operational rigor. You're energized by creating structure, 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.

As a Chief of Staff, you will: 

• Serve as Strategic Proxy: Act as the CEO's trusted advisor and decision-making partner. 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.

Success in this role looks like: 

• First 90 days: Build a deep understanding of the MA business model, operating context, and leadership dynamics. Establish trust with the CEO and executive team. Take ownership of 2-3 high-priority initiatives and deliver visible impact.
• First 6 months: Independently drive multiple complex initiatives end-to-end. Establish operating rhythms that improve decision quality and execution velocity. Be viewed as a central integrator and force multiplier across the MA organization.
• First year: Play a pivotal role in shaping and executing the MA strategy. Deliver measurable contributions to growth, profitability, and operational leverage. Leave behind systems, processes, and operating mechanisms that are materially stronger than you found them.

You should get in touch if: 

• You have 10+ years in elite operating environments: Chief of Staff roles, top-tier consulting (McKinsey, Bain, BCG), investing, startup leadership, strategic operations, or similar high-judgment tracks.
• 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 Overview: 

• 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!

About Clover: We are reinventing health insurance by combining the power of data with human empathy to keep our members healthier. We believe the healthcare system is broken, so we've created custom software and analytics to empower our clinical staff to intervene and provide personalized care to the people who need it most.

We always put our members first, and our success as a team is measured by the quality of life of the people we serve. Those who work at Clover are passionate and mission-driven individuals with diverse areas of expertise, working together to solve the most complicated problem in the world: healthcare.

From Clover’s inception, Diversity & Inclusion have always been key to our success. We are an Equal Opportunity Employer and our employees are people with different strengths, experiences and backgrounds, who share a passion for improving people's lives. Diversity not only includes race and gender identity, but also age, disability status, veteran status, sexual orientation, religion and many other parts of one’s identity. All of our employee’s points of view are key to our success, and inclusion is everyone's responsibility.

#LI-REMOTE

Pursuant to the San Francisco Fair Chance Ordinance, we will consider for employment qualified applicants with arrest and conviction records. We are an E-Verify company.