Chief of Staff

Chief of Staff – EasyHealth

Location: Remote

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Reports to: CEO  

Status: Full-Time  

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Who Are We?  

Do you want to be part of a passionate team fixing our broken healthcare system?  

EasyHealth is building the AI-powered infrastructure that transforms how care is delivered in the home. We serve Medicare, Medicaid, and ACA populations through a national clinical network, predictive AI logistics, and integrated diagnostics—all designed to catch conditions before they escalate. With significant growth and momentum across the top health plans in the country, we’re scaling fast and operating profitably.

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We’re now looking for a Chief of Staff to the CEO to help us accelerate this next phase of growth.

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What You’ll Do  

You’ll act as an operational and strategic right hand to the CEO. You’ll tackle the highest-leverage challenges across the business—translating strategy into execution, unblocking key initiatives, and building systems to help the company scale with clarity and speed.

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Key Responsibilities  

• Drive alignment across executive leadership on priorities, KPIs, and OKRs  
• Own and project manage high-stakes cross-functional initiatives (e.g. fundraising readiness, AI deployment, operational transformation)  
• Lead CEO office operations: agenda setting, prep, and follow-ups for exec meetings, board calls, and investor updates  
• Partner with finance, ops, product, and people teams to identify bottlenecks and unlock organizational velocity  
• Build dashboards, write memos, and surface insights that drive performance and accountability  
• Take on special projects that range from integrating acquisitions to standing up new growth initiatives  
• Serve as a culture carrier and help reinforce clarity, urgency, and execution discipline throughout the org  

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What We’re Looking For  

• 2-4 years of experience in consulting, strategy, BizOps, VC-backed startups, or healthcare (Medicare/Medicaid/ACA experience is a plus)  
• High IQ and EQ — a systems thinker who builds trust quickly and communicates crisply  
• Proven ability to manage complex projects with multiple stakeholders and shifting priorities  
• Data fluency and operational rigor — you’re comfortable in dashboards, financial models, Airtable, or Power BI  
• Bias toward action, high accountability, and comfort with ambiguity  
• Deep alignment with our mission to transform the healthcare experience for vulnerable populations  
• Bachelor’s degree required; MBA or advanced degree a plus  

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Why This Role, Why Now  

• Direct seat at the table: Work side-by-side with the CEO and exec team during a critical scale-up period  
• Major impact: Help shape strategy, streamline execution, and push the company into profitability  
• Growth runway: We’re expanding into Medicaid and ACA, launching new AI tools, and doubling visit volume  

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Benefits  

• Competitive compensation and equity  
• Comprehensive health, dental, vision, and life insurance  
• Flexible remote work environment  
• A mission-driven, high-performance team building something that truly matters