Chief of Staff to CEO, Medicare Advantage

Role overview

This is a senior, high-influence operating role supporting the CEO of a fast-growing Medicare Advantage business in the United States. You will act as a close extension of the CEO, bringing clarity to strategy, execution, and organizational priorities in a demanding healthcare setting. The position combines strategic judgment with hands-on delivery and requires someone who can convert uncertainty into structured decisions and measurable progress. You will work across clinical, finance, operations, and growth functions to strengthen alignment and speed up execution. The role is ideal for a builder who performs well without established playbooks and can create order where processes are still evolving.

You will also help define operating systems, decision-making cadences, and cross-functional execution frameworks that support efficient scaling. This is a rare opportunity to have a direct impact on the direction of a mission-driven healthcare organization.

Key accountabilities

• Act as a strategic stand-in for the CEO in important discussions, helping shape decisions with structured analysis and clear recommendations.
• Set and maintain priorities across the Medicare Advantage organization so efforts stay centered on growth, quality, and financial goals.
• Coordinate delivery of strategic initiatives across clinical, operations, finance, and growth teams while holding owners accountable for results.
• Build and refine operating systems such as executive cadences, reporting routines, and decision frameworks that improve organizational efficiency.
• Spot ways to use AI and other emerging technologies to reduce friction, improve decision quality, and accelerate execution.
• Create executive-ready materials including board presentations, strategy documents, and performance narratives that make complex information easier to understand.
• Remove blockers by clarifying responsibility, aligning stakeholders, and resolving ambiguity across teams.
• Set up tracking tools and performance frameworks that improve visibility into business outcomes and execution status.

Requirements

• At least 10 years of experience in fast-moving environments such as startups, scale-ups, consulting, or strategic operations roles with full ownership of outcomes.
• Background as a Chief of Staff, strategic operator, or similar senior cross-functional leadership role.
• Ability to work effectively in uncertainty, build structure from the ground up, and translate strategy into action.
• Strong record of influencing senior stakeholders and delivering results without direct authority.
• Advanced comfort with AI tools and a demonstrated ability to use AI to improve workflows, decisions, or operational efficiency.
• Strong systems thinking and the ability to design processes and operating models that can scale.
• Excellent communication skills with the ability to simplify complexity for executive audiences.
• Strong prioritization and judgment under pressure in rapidly changing environments.
• Healthcare or Medicare Advantage experience is helpful but not mandatory; quick learning and adaptability are essential.

Benefits

• Competitive base pay between USD 180,000 and USD 230,000.
• Equity opportunity and performance-linked bonus potential.
• Medical, dental, and vision coverage.
• 401(k) retirement plan with company match.
• Remote-first working setup with flexibility.
• Flexible PTO along with company holidays.
• Paid parental leave for all new parents.
• Mental health support and wellness resources.
• Employee stock purchase program plus additional financial wellness benefits.
• Home office setup reimbursement and monthly connectivity allowance.
• Professional development and learning support.
• High-level executive exposure with direct influence on company strategy.

Additional information

This role is posted on behalf of a partner company, which handles applications and the next steps in the hiring process. Applications are reviewed through an AI-assisted matching workflow so candidates can be assessed quickly and fairly against the role’s core requirements. The shortlist is then shared with the hiring company, while interviews, assessments, and final decisions are managed internally by that team.

Data privacy notice

By applying, you consent to the processing of your personal data for candidate evaluation and for sharing relevant details with the hiring employer. The processing is based on legitimate interest and pre-contractual measures under applicable data protection laws, including GDPR. You may request access, correction, deletion, or objection to processing at any time.

AI tools may be used to support parts of the recruitment process, including application review, resume analysis, response assessment, and identification of possible inconsistencies or verification signals based on the information provided. These tools support the recruitment team but do not replace human judgment; final hiring decisions are made by people. If you want more information about data processing, you may contact the company directly.