About us

We are a very profitable and fast-growing healthcare startup — a small and mighty team of 150 helping people find, enroll in and use ACA health coverage. We’ve doubled in each of the past four years and are now the largest ACA enrollment platform after healthcare.gov, having helped over 10 million people enroll in health coverage. We’re a mission-driven team that advocates for and cares deeply about the people we serve.

We are a double bottom-line company: revenues and enrollments in ACA coverage. The ACA brings high-quality, comprehensive, and affordable health coverage within reach for low-income Americans. We exist to make that promise a reality. Your contribution will positively affect hundreds of thousands of people, helping them to navigate the complex and confusing health insurance industry and to access health care when they need it.

We are committed to building a team balanced in representation to best serve the people who use our products. We believe in creating inclusive and equitable spaces, which build trust and respect and foster a sense of belonging. These values are at the core of our culture, and we genuinely believe they will continue to lead our organization to successful outcomes.

About the Role

The CEO empowers and enables the individuals in the company to achieve their objectives and fulfill their potential. This means providing resources, removing obstacles, communicating strategy, having difficult conversations, and cleaning up messes so that others focus on what they do best. As we’ve grown, the range of opportunities and problems has expanded similarly with our growth; the CEO needs a strategic partner to help bring order to the chaos.

The Chief of Staff is a service role, focused on expanding the range of services the CEO can provide to the team. You will run the Office of the CEO, managing your EA Partner and reporting directly to the CEO. This is a remote-friendly role for candidates based in the US.

You will significantly increase the CEO’s bandwidth by:

    • Attending meetings and managing follow ups
    • Holding the CEO and other team members accountable
    • Learning, filtering, and presenting new information to the CEO
    • Drafting presentations for all partners including the Board of the company
    • Eventually attending meetings and making decisions on the CEO’s behalf
    • Managing the daily operations of the office of the CEO, evaluating all requests for the CEO’s time and working collaboratively with the Executive Assistant to ensure time spent is aligned with the priorities of the organization
    • Handling the oversight and execution of important projects that do not neatly fit within the organizational chart or that fall between departments or leadership responsibilities
    • Serving as a trusted partner and advisor to the CEO and executive team
    • Building enduring and meaningful relationships with the broader team

You Have:

    • At least 3 years of experience in a startup, finance, consulting, complex program/project management or other rigorous roles blending strategy and analysis
    • Collaborative and low-ego mindset; you work well with all kinds of personalities; you work well with teams across multiple geographies

What We Offer:

    • Remote-first company
    • Great compensation package with meaningful equity in a high growth, profitable company
    • Excellent benefits package that includes health, vision, and dental coverage for you, your spouse and dependents
    • Monthly grocery stipend and home internet reimbursement
    • 401K w/ a match after a grace period
    • Employee assistance program
    • Parental leave
    • 4 weeks paid vacation in addition to paid holidays
    • Home office budget for remote team members
    • Disability insurance

We’re building a diverse and inclusive work environment where we learn from each other. We welcome and encourage people of diverse backgrounds, experiences, identities, abilities and perspectives to apply. We are an equal opportunity employer and a fun place to work. Come join the team at HealthSherpa.