Remote Executive Assistant

About Sailor Health

Sailor Health is revolutionizing the aging experience for older adults, addressing one of the fastest-growing and most underserved healthcare segments in America. With over 60 million seniors expected to make up nearly 25% of the population by 2030, we’re entering a period of unprecedented demand for care. Yet, today, millions of older adults remain isolated, underserved, and struggling with mental health challenges such as anxiety, depression, loneliness without adequate support.

We are a remote but tight-knit team who cares deeply about each other and our mission. Join us on our mission to redefine the golden years, enabling older adults across the nation to live happier, healthier, and more fulfilling lives.

 

About the Role

Title: Executive Assistant to the Founders

Location: Remote - Canada (Eastern time zone)

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.

This is our first EA hire, and it goes beyond pure calendar management. You'll be the operational backbone of the founding team – owning scheduling and logistics, running our NYC office, supporting new hires with HR and onboarding workflows, and making sure nothing falls through the cracks as we scale.

If you're excited to be the person who makes everything work at a fast-growing digital health company, we'd love to meet you.

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.

• Experience in an EA or operations role is a plus, but not required – we're open to recent graduates who are sharp, hungry, and ready to grow alongside the founders of a fast-scaling company.

Your Key Responsibilities

This role moves fast sits at the center of the company, ideal for candidates looking for high-intensity and high-exposure.

• 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

• Support the co-founders in preparing materials for internal and external meetings

• 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.

If this sounds like you, we’d love to connect. Join us in redefining what it means to age with dignity, connection, and mental wellness.