Chief of Staff

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.