Executive Assistant

About The Role

Title: Executive Assistant to the Founders
Location: NYC (Soho) - 3-5 days in office
At Sailor Health, the founders are deeply hands-on across every function – from clinical operations and payer strategy to hiring, compliance, and product. We're looking for an Executive Assistant to work directly with our co-founders to keep the company running smoothly behind the scenes.

Who You Are

• You're exceptionally organized with a service-oriented mindset – you take genuine pride in making the people around you more effective.
• You have impeccable attention to detail and follow-through, and you never let a ball drop.
• You're proactive by nature – you anticipate needs and solve problems before they surface, rather than waiting to be asked.
• You respond quickly, communicate clearly, and maintain composure when priorities shift.
• You understand the weight of confidentiality.
• You're a fast learner who's genuinely excited to go deep on new domains – whether that's HR compliance protocols, expense management systems, or new operational workflows.
• You operate independently, figure things out, and move with urgency.

Your Key Responsibilities

• Support people operations workflows, including onboarding new hires, managing employee records, coordinating benefits enrollment, and tracking compliance items.
• Own both founders' calendars, scheduling, and travel logistics.
• Coordinate team events and culture-building activities that keep our crew happy and connected.
• Own operational workflows in the founders' office end-to-end.
• Manage day-to-day office operations of our NYC office, including supplies, vendor relationships, meal coordination, and maintaining a productive workspace.
• Serve as a key point of contact for the team, triaging requests and communications to the founders and ensuring timely follow-through.
• Handle ad hoc projects and research that support the founders across strategy, operations, and company-building.

Why Join Sailor Health

• Mission with impact. Help bring life-changing care to a population that’s too often overlooked.
• Growth and ownership. Unique opportunity to work directly with the founders of the company, where you'll be exposed to extraordinary growth opportunities.
• Remote-first team. Enjoy the flexibility of remote work while staying closely connected with a thoughtful, collaborative team rooted in purpose.
• Make someone’s day – every day. Your work helps older adults and their families feel seen, supported, and cared for.

Our Values

• Make your Grandparents Proud: Remember why you’re here and build the standard of care you wish your grandparents received.
• Best Ideas Win: We strip problems down to first principles and challenge each other – but once a decision is made, we row as one.
• Go Fast and Far: We have a burning sense of urgency AND we go the extra mile.
• Do What It Takes To Be #1: We obsess over excellence and challenge ourselves and each other to actualize our best selves.
• Happy Crew: A miserable crew rows slow. A happy crew rows fast. Fun is a performance metric.

Our Offer to You

• Competitive salary
• Comprehensive benefits, including medical, dental & vision insurance
• Lunch and dinner in our beautiful Soho office covered by Sailor
• Talkspace
• HealthAdvocate
• Teledoc Health

Compensation Range

$85K - $90K