Chief of Staff

Chief of Staff to CEO

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Location: New York - In Office, Full Time (no WFH)

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Overview

CoverRight is an insurance technology (insurtech) startup on a mission to make Medicare more accessible to the 60 million beneficiaries across the country.

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Every day, 10,000 Americans retire and face one of the most complex and important decisions of their lives — choosing the right health insurance. We exist to make that decision simpler, smarter, and more personalized.

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We are early, growing quickly, and intentional about building a high-performance team.

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What We Are About

CoverRight's pace and intensity is not for everyone. Intelligence is table stakes.

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To succeed here, you need extreme speed, ownership, and flexibility.

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Our best team members don’t wait for direction. They internalize the mission, define the problem, design the solution, and deliver outcomes that are faster and better than expected.

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We are a tight-knit, scrappy, high-performance team. We move quickly, take calculated risks, and execute relentlessly — while caring deeply about our customers and each other.

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We have ambitious growth goals and are looking for people who can move mountains to get things done.

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The Role

This is not a traditional Chief of Staff role.

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You will work directly with the CEO as a force multiplier — operating across strategy, execution, and operations. You will be dropped into the company’s highest priority problems and expected to drive them to resolution.

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You are not here to “support” — you are here to own outcomes.

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This role is ideal for someone who wants to operate at the center of a high-growth startup and eventually step into senior leadership.

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> Expect to be on call 7 days— this is NOT a 9–5 Mon-Fri role. <<

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What You Will Do

• Partner directly with the CEO on the highest-leverage priorities in the company
• Lead complex, cross-functional initiatives from ambiguity to execution
• Drive alignment across teams and stakeholders — ensuring nothing slips
• Act as a true thought partner — challenge assumptions and improve decisions
• Identify bottlenecks, inefficiencies, and emerging issues — and solve them proactively
• Step into any function (operations, growth, partnerships, product) and take ownership when needed
• Manage internal and external stakeholders, including senior leaders, with maturity and precision
• Ensure the CEO’s time and focus are deployed for maximum impact

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Who You Are

• 4–6 years of experience in high-growth startup, investment banking or top-tier management consulting
• Exceptional commercial judgment, with a deep understanding of stakeholder incentives and the ability to lead and influence negotiations in complex, high-stakes situations 
• Proven track record of owning and delivering complex, multi-stakeholder projects
• Exceptional organizational and project management skills — able to operate effectively in chaos
• Independent, decisive thinker - not a task-taker or pure number cruncher
• High emotional intelligence - able to navigate personalities, conflict, and senior stakeholders
• Comfortable operating in ambiguity, speed, and pressure
• Relentless ownership mindset - you do what it takes to get the job done

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What Success Looks Like

• The CEO is operating at significantly higher leverage
• The company moves faster on its most critical priorities
• Teams are aligned, accountable, and executing effectively
• Problems are identified and solved before they escalate

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Why This Role

This is a front-row seat to building and scaling a company.

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You will have direct exposure to strategy, execution, and leadership - and the opportunity to accelerate into senior roles as the company grows.

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There is significant upside for the right person - but also a high bar.