Chief of Staff

About Us

We are a very profitable and fast-growing healthcare startup—a small and mighty team of 200 helping people find and enroll in ACA health coverage. As the largest health insurance exchange for the ACA, enrolling more individuals than healthcare.gov and all our competitors, we have helped over 10 million people enroll in health coverage to date in 2024. We're a mission-driven team that advocates for and cares deeply about the people we serve.

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

We are committed to building a team balanced in representation to serve best the people who use our products. We believe in creating inclusive and equitable spaces that build trust and respect and foster a sense of belonging. These values are at the core of our culture and 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 can 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 that reports directly to the CEO and focuses on expanding the range of services the CEO can provide to the team. This is a remote-friendly role for candidates based in the US.

The base salary range is $154,000-$235,000 + bonus + equity + benefits. Within the range, individual pay is determined by work location and additional factors, including job-related skills, and experience. Your recruiter can share more about the specific salary range for your preferred location during the hiring process.

You Will:

• Handle the oversight and execution of important projects that do not neatly fit within the organizational chart or that fall between departments or leadership responsibilities

• Partner with the CEO and executive team on our strategic initiatives from development through successful execution

• Run company processes such as quarterly/annual planning, investment requests, company all-hands, and company objective-setting

• Facilitate communication among the executive team and the broader company, making sure each function has the information they need to succeed

• Attend meetings and manage follow-ups with the CEO, occasionally being a proxy for the CEO

• Analyze data, prepare reports, and draft presentations for partners, including investors and the Board of the company

• Be a trusted collaborator, advisor, and accountability partner to the CEO and executive team

• Manage the daily operations of the Office of the CEO by 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

You Have:

• 5+ years of experience in finance, consulting, complex program management, or other rigorous roles blending strategy and analysis

• A collaborative mindset that works well with all kinds of personalities across distributed teams

• The ability to distill complex ideas, disparate data, and high-level goals into actionable plans

• Hands-on operational skills and the ability to guide complex projects forward

• Proficiency in Excel/Google Sheets (can perform complex functions) and PowerPoint/Google Slides

• SQL and Tableau/Mixpanel experience (bonus)

• Multi-sided marketplace experience (bonus)

• Startup experience (bonus)

What We Offer (Full-time, Not Temporary/Not Seasonal)

• Remote-first company (US-based remote only)

• Great compensation package at a high-growth, profitable company

• Excellent benefits package that includes health, vision, and dental coverage for you, your spouse, and dependents

• HSA/FSA options with corresponding contribution limits

• Monthly grocery stipend and home internet reimbursement

• 401K w/ a match after a grace period

• Life and AD&D coverage

• Disability insurance (Short and Long Term)

• Parental leave

• Four (4) weeks of paid vacation in addition to paid holidays

• Home office budget for remote team members

• Mental health and other wellbeing support programs through a partner network

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! #LI-Remote