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Clover Health · 3 days ago

Chief of Staff to CEO, Medicare Advantage

United States

Full-time

Remote

Director/Executive

$160K/yr - $190K/yr

10+ years exp

Clover Health is seeking a results-driven Chief of Staff to the Medicare Advantage CEO to partner closely with the MA CEO and Executive team. The Chief of Staff will serve as a trusted advisor, manage executive-level priorities, and lead complex, cross-functional initiatives to ensure the MA business delivers on its goals.

Health CareHealth InsuranceHospitalMedical

Responsibilities

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

Qualification

Healthcare strategyAnalytical skillsProject managementExecutive communicationStrategic planningInfluencing skillsOrganizational rigorEmotional intelligence

Required

10+ years of experience in Chief of Staff roles, management consulting, healthcare strategy, or complex operating environments

Bachelor's degree (required); advanced degree a plus

Exceptional analytical, communication, and project management skills

Excellent written and verbal communication

High emotional intelligence, sound judgment, and ability to influence without authority

Preferred

Strong understanding of healthcare, insurance, or Medicare Advantage economics (strongly preferred)

Benefits

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.

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!