Senior Executive Assistant

About Us

We are a very profitable and fast-growing healthcare startup—a small and mighty team of 230 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 15 million people enroll in health coverage to date through 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.

HealthSherpa is a fully remote company and was recognized as a 2026 Best Remote Place to Work by Built In, reflecting our commitment to building a people-first culture rooted in trust, flexibility, and impact.

About the Role

We are looking for a Senior Executive Assistant to support our CEO. There is no average day in this role, and you are not an average executive partner. You neutralize chaos before it materializes, rip holes in the space-time continuum for peak productivity, and serve as the bedrock for the CEO's efficiency.

This is a hybrid position located in downtown Sacramento. There will be some flexibility with work location depending on the CEO's priorities, with the baseline expectation of four days/week in the office. As a member of the Office of the CEO, you will report to the Executive Assistant Manager.

The base salary range is $120,000-$160,000 + equity + benefits. Within the range, individual pay is determined by additional factors, including job-related skills and experience. We are open to candidates from anywhere in the US and will provide relocation support.

You Will:

• Deliver excellence in all foundational EA tasks: calendar management, email handling, travel, expenses, and administrative support

• Manage the CEO’s time and calendar by balancing work and personal priorities, resolving conflicts, and ensuring productive use of time

• Oversee special projects from initiation to completion

• Provide personal assistance to the CEO, including managing household vendors, errands, and occasional family logistics, with the goal of reducing personal distractions (Less than 25% time)

You Have:

• 5+ years of proven experience as a senior executive assistant supporting C-level executives, across multiple time zones

• A solutions-oriented mindset and operational fluency to address unexpected demands and changes in timelines

• Proficiency in various tech tools, including but not limited to Google Workspace and Slack

• Must have reliable transportation and be located in or near Sacramento

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
  

As an organization, we value creating an inclusive and accessible experience. If you require reasonable accommodations during the application or interview process, please let your recruiter know.

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!