About us

HealthSherpa is a mission-driven company building the nation’s most comprehensive health insurance marketplace. We exist to help as many people find and enroll in ACA health coverage, and our success speaks for itself: we’ve helped over 6 million people enroll in health coverage, and are now the largest ACA enrollment platform in the country after healthcare.gov.

Our team of 80 helps bring high-quality, comprehensive, and affordable health coverage within reach for low-income Americans. Your contribution will positively affect millions of people, helping them to navigate the complex and confusing health insurance industry and to access health care when they need it.

The role

As the executive assistant supporting the CEO at HealthSherpa, you will have a crucial role in our mission to bring healthcare to all Americans while simultaneously defining an EA’s reach across the company. You will have a broad impact across the entire organization, by ensuring that the CEO is focusing on the most important things. You will align your executive both internally and externally, providing them with the administrative support they need to lead more effectively.

We’re looking for someone who enjoys streamlining hectic days and succeeds in the face of limited resources. We value someone who is highly organized, extremely adaptable, and pleasantly pushy. You will report to the CEO.

You Will:

    • Form trusting relationships with executives’ customers, team, and contacts
    • Coordinate meetings, managing dynamic and packed calendars for multiple executives
    • Develop and organize materials, briefs, and presentations to prepare executives for important meetings
    • Take ownership of communications with professional correspondence
    • Manage special ad hoc projects while performing daily responsibilities
    • Create and document repeatable processes (for yourself) to ensure things don’t get lost and so we can improve and grow efficiency
    • Maintain and facilitate expense reports
    • Be a strategic partner

You Enjoy:

    • Sorting through the minutiae because you understand that the whole is composed of many, many small details, but you also recognize that the various parts are worthless if the goal is unmet
    • The efficiency and efficacy afforded by keyboard shortcuts, templates, repeatable processes
    • Solving the puzzle of executive calendars and take pleasure in finding ways to free up time for your executives, and you do it all with a cheerful and calm presence
    • Learning and are always looking ahead so that you can provide appropriate solutions, often anticipating needs before they arise
    • Being the necessary holder of sensitive information and thrive in your role as an information relay for your executive

You Have:

    • At least two years of experience supporting a C-suite executive
    • Experience managing a high-volume workload effectively
    • Experience handling confidential information discreetly
    • Experience with web-based scheduling and collaboration tools
    • Experience coordinating complex schedules and logistics, at times, across multiple time zones

What We Offer

    • Meaningful compensation package with equity in a high-growth, profitable company
    • Health, vision, and dental coverage for you, your spouse, and dependents
    • A shiny Mac and the other productivity accessories you need
    • 401K after a grace period
    • Ample vacation and holidays
    • Catered or restaurant lunch, daily
    • Free parking / Commuter benefit

Physical requirements & work conditions

– Work is performed primarily in a standard office environment

– Physically able to reach, stretch, bend, walk, and navigate stairways

The physical demands and work environment characteristics described here are representative of those that must be met by an employee to successfully perform the essential functions of this job. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.

Employees may, among other things, be required to undergo background investigations or security checks, or meet certain standards dictated by law, regulation or contracts, and as a prerequisite to employment candidates may be asked to consent to a due diligence/background investigation. As a condition to hiring and continued employment, we require all employees to meet those requirements that are necessary to fulfill their individual roles.