Chief of Staff to CEO, Medicare Advantage

This is a fully remote position, open to applicants in United States.

📋 Description

• Act as the CEO's Strategic Proxy: Function as the trusted representative of the CEO, not merely as an advisor, but as someone capable of making decisions and representing her in high-pressure situations.

• Prioritize Ruthlessly: Rank initiatives based on growth, quality, and financial goals. Take ownership of the strategic roadmap and ensure the organization concentrates on initiatives that propel the business forward.

• Lead Cross-Functional Execution: Manage intricate initiatives across clinical, operations, finance, and growth sectors. Align leadership around explicit decisions and establish enduring accountability mechanisms.

• Develop Operating Systems: Create the rhythms, tracking systems, and decision-making processes necessary for the CEO to effectively manage the business.

• Leverage AI and Emerging Technologies: Spot opportunities to implement AI-driven tools that enhance execution, elevate decision-making quality, and provide operational leverage.

• Prepare Executive Materials: Generate high-quality narratives and presentations for the CEO, Board, and executive stakeholders.

• Influence Without Formal Authority: Cultivate trust within the organization. Unite leaders around common priorities.

• Navigate Uncertainty: Offer clarity when the way forward is unclear and facilitate thoughtful alignment amidst conflicting priorities.

⛳️ Requirements

• You possess over 10 years of experience in dynamic, high-growth environments — including leadership in startups or scale-ups, strategic operations, or similarly demanding roles where you were accountable for outcomes rather than just programs.

• You are a builder and systems thinker: adept at creating structure from ambiguity, designing scalable operating models, and translating strategy into impactful execution.

• You have a strong understanding of AI: experienced in deploying AI to enhance execution and unlock leverage, with an eye for opportunities that others may overlook.

• You excel in rapid prioritization within ambiguous environments, transitioning smoothly from strategy to execution, knowing when to assert and when to step back.

• You are highly skilled in relationship-building and influencing across various functions without formal authority. You establish trust through clarity, quality, and speed — rather than positional power.

• Experience in healthcare or Medicare Advantage is advantageous but not mandatory. A willingness and aptitude for quick learning is crucial. We have seen effective Chief of Staff operators emerge from consulting, technology, finance, and other sectors.

🏝️ Benefits

• Financial Well-Being: We aim to attract and retain top talent with a competitive base salary and equity opportunities. Our performance-based bonus program, 401k matching, and regular compensation reviews are designed to recognize and reward outstanding contributions.

• Physical Well-Being: We prioritize the health of our employees and their families by providing comprehensive medical, dental, and vision coverage. Your health is important to us, and we invest in ensuring you have access to quality healthcare.

• Mental Well-Being: Acknowledging the significance of mental health in enhancing productivity and maintaining work-life balance, 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 dedicated to nurturing our internal talent through learning programs, mentorship, professional development funding, and regular feedback and performance reviews.

• Additional Perks: Employee Stock Purchase Plan (ESPP) providing discounted equity opportunities, reimbursement for office setup expenses, monthly cell phone & internet stipends, a remote-first culture fostering collaboration with global teams, paid parental leave for all new parents, and much more!