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Posted May 13, 2026

Remote Lead Chief of Staff

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This position is posted by Jobgether on behalf of a partner company. We are currently looking for a Chief of Staff to CEO - REMOTE. In this pivotal role, you'll operate as a trusted advisor to the CEO, managing multiple strategic initiatives that drive the company's growth. Your expertise will help streamline operations and enhance decision-making across the organization. This role requires a blend of strategic vision and hands-on execution to build the operating systems necessary for scaling. You will influence leaders across various departments, ensuring alignment and accountability while creating structure and clarity in an ever-changing environment. Accountabilities • Serve as Strategic Proxy: Act as the CEO's trusted advisor and decision-making partner. • Ruthlessly Prioritize: Force-rank initiatives against growth, quality, and financial objectives. • Drive Cross-Functional Execution: Orchestrate complex initiatives across clinical, operations, finance, and growth. • Build Operating Systems: Establish rhythms and decision cadences essential for effective business operations. • Harness AI and Emerging Technology: Identify opportunities to deploy AI-powered tools that enhance execution. • Prepare Executive Materials: Create narratives and presentations that simplify complexity. • Influence Without Authority: Build trust and clarity across the organization. • Navigate Ambiguity: Provide direction and unblock stalled initiatives. Requirements • 10+ years in elite operating environments such as Chief of Staff roles or top-tier consulting. • Proven ability to create structure from ambiguity and design scalable operating models. • Fluency in AI and its application in accelerating execution. • Exceptional skills in rapid prioritization and decision-making in ambiguous environments. • Strong relationship-building and influencing capabilities without formal authority. • Experience in healthcare or Medicare Advantage is a plus but not required. Benefits • Competitive base salary and equity opportunities. • Performance-based bonus program and 401k matching. • Comprehensive medical, dental, and vision coverage. • Mental health resources and a flexible time-off policy. • Employee Stock Purchase Plan (ESPP) with discounted equity opportunities. • Reimbursement for office setup expenses. • Monthly cell phone and internet stipend. • Remote-first culture supporting collaboration with global teams. • Paid parental leave for all new parents. Apply tot his job Apply To this Job