Executive Assistant to Founders (Remote, Canada)

About the role

Sailor Health is seeking a proactive Executive Assistant to support its co‑founders. This remote, Canada‑based position will serve as the operational backbone of the founding team, ensuring smooth day‑to‑day operations and enabling the company to scale efficiently.

Key responsibilities

• Manage both founders' calendars, schedule meetings, and coordinate travel logistics.
• Run the NYC office operations, including supplies, mail, and facility needs.
• Support people‑operations workflows: onboarding new hires, maintaining employee records, coordinating benefits enrollment, and tracking compliance items.
• Organise team events and culture‑building activities to keep the crew connected.
• Own end‑to‑end operational workflows for the founders' office, including expense management and documentation.

Required profile

• Exceptionally organized with a service‑oriented mindset.
• Impeccable attention to detail and strong follow‑through.
• Proactive problem‑solver who anticipates needs.
• Excellent written and verbal communication; calm under shifting priorities.
• High sense of confidentiality and professionalism.
• Fast learner eager to dive into HR compliance, expense systems, and new operational processes.

Required skills

What we offer

• Opportunity to be the first EA hire and shape the role.
• Remote work with a supportive, mission‑driven team.
• High exposure to founders and fast‑growing digital health environment.