Job Description

Chief of Staff to CEO

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

Overview

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

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.

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

What We Are About

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

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

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.

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.

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

The Role

This is not a traditional Chief of Staff role.

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.

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

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

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

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

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

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

Why This Role 

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

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

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

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