Chief of Staff to CEO, Medicare Advantage

Clover's Medicare Advantage business is scaling rapidly. The MA CEO needs a Chief of Staff who can operate as a trusted proxy, ruthlessly prioritize across competing initiatives, and build the operating systems required to execute at scale. This is a high-leverage operating role for someone who thrives at the intersection of strategy and execution. You'll drive critical cross-functional initiatives, translate ambiguity into action, and establish operating rhythms that improve decision quality and velocity. You'll work across clinical, operations, finance, and growth — aligning leaders, unblocking progress, and ensuring the business delivers. The ideal candidate is a decisive operator who moves fast, communicates crisply, and knows how to get things done in ambiguous, fast-moving environments. This role is designed for builders who default to action — people who create structure from chaos, not people who need structure to operate effectively. You're energized by driving tangible outcomes and leveraging AI to multiply impact. You're comfortable with ambiguity, move with conviction, and know when to escalate and when to execute. As a Chief of Staff, you will: Serve as Strategic Proxy : Act as the CEO's trusted proxy — not just an advisor, but someone who can represent her in high-stakes rooms and make decisions on her behalf. You communicate with clarity and and support high-sta...