Chief of Staff to CEO, Medicare Advantage

Clover Health

full-time

Posted on: 1/13/2026

Location Type: Remote

✨ AI Apply

💰 $160,000 - $190,000 per year

About the role

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.

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

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!

Tip: use these terms in your resume and cover letter to boost ATS matches.

strategic planningOKR developmentbusiness analysisproject managementdata analysis

communicationemotional intelligenceinfluence without authorityjudgmentproblem-solving

Bachelor's degreeadvanced degree