Chief of Staff to CEO, Medicare Advantage

Role Summary

Clover Health is seeking a results-driven Chief of Staff to the Medicare Advantage CEO to partner closely with the MA CEO, MA Executive team, Executive Assistant to the CEO, and other Chiefs of Staff. The Chief of Staff to the Medicare Advantage CEO will serve as a trusted advisor, thought partner, and operational leader to the Medicare Advantage CEO. You will lead complex, cross-functional initiatives, manage executive-level priorities, and ensure the CEO is positioned to focus on the most critical decisions and opportunities. You will work closely with leaders across clinical, operations, finance and growth to ensure the MA business delivers on its goals.

The ideal candidate is a data-driven, principle-oriented leader with exceptional judgment, organizational rigor, and influence, who thrives in fast-paced environments and is passionate about improving health outcomes for seniors.

As a Chief of Staff, you will:

• Serve as a strategic advisor and proxy for the MA CEO, supporting decision-making through rigorous analysis, first-principles thinking, and business judgment.
• Support strategic planning and annual OKR development.
• Drive execution of top Medicare Advantage priorities, ensuring alignment with growth, quality, and financial objectives.
• Partner with cross-functional leaders to align workstreams to MA business objectives spanning clinical performance, Stars, risk adjustment, operations, and growth.
• Provide regular, structured updates to the CEO on initiative progress, risks, and tradeoffs; proactively surface and remove blockers.
• Establish operating rhythms, goal tracking, and accountability mechanisms across the MA organization.
• Prepare high-quality executive materials, narratives, and presentations for internal, board and external stakeholders.
• Partner closely with the CEO’s Executive Assistant to optimize time, agenda, and information flow.
• Ensure meetings are purposeful, outcomes-driven, and followed by clear execution plans.
• Handle highly confidential and sensitive information with discretion.

Success in this role looks like:

• In your first 90 days, you will:
  • Establish a clear operating framework for the Chief of Staff function.
  • Build trust with the CEO and MA leadership team.
  • Deliver on several high-priority initiatives with visible impact.
• After 6 months you will:
  • Independently drive multiple complex initiatives end-to-end.
  • Be viewed as a central integrator and force multiplier across the MA organization.
• Future success in this role includes:
  • Strategic Impact: Play a pivotal role in shaping and executing the company’s strategic vision; demonstrate significant contributions to the company’s growth, profitability, and market position.
  • Organizational Development: Foster a culture of continuous improvement, innovation, and excellence within the organization.

You should get in touch if:

• You have 10+ years of experience in Chief of Staff roles, management consulting, healthcare strategy, or complex operating environments.
• You have a Bachelor’s degree (required); advanced degree a plus.
• You have a strong understanding of healthcare, insurance, or Medicare Advantage economics (strongly preferred).
• You have exceptional analytical, communication, and project management skills.
• You have excellent written and verbal communication.
• You have high emotional intelligence, sound judgment, and ability to influence without authority.

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.