Executive Assistant to CEO & CTO - Startup Operations Pro

Flagler Health, Inc; New York, Northern (NY, KY); Hybrid; USD 75,000 - 110,000; Full time

Job summary

Flagler Health, Inc is building the clinical operating system for modern musculoskeletal care from their NYC base. This Executive Assistant role supports the CEO and CTO, keeping calendars tight, travel smooth, and the front of house welcoming for guests, investors, and candidates.

The successful candidate will be exceptionally organized, comfortable in a fast-moving startup environment, and will help run the upcoming office move, while coordinating cross-functional operations and events.

Qualifications

• 2–4+ years of administrative or office management experience supporting senior executives, ideally at a startup where the scope of the job changed every quarter.
• Demonstrated excellence in high-volume calendar management and travel logistics, with a track record of anticipating needs before they are raised.
• Outstanding written and verbal communication, with the judgment to act as a first point of contact for customers, candidates, and investors.
• Genuine fluency with modern productivity tools including Google Workspace, Slack, Notion, and Zoom, and an interest in using AI to streamline administrative work.
• Complete discretion and sound judgment when handling compensation conversations, board material, and sensitive customer issues.
• A bias toward action and the resourcefulness to fix what is broken rather than upscale it.
• Reliability and punctuality, including a commitment to being in our SoHo office five days a week.
• A flexible and positive approach to a role that ranges from expense reports to a last-minute investor dinner.

Responsibilities

• Own end-to-end calendar management for the CEO and CTO, protecting focus time and resolving conflicts before they surface
• Make sure both executives walk into every meeting prepared, with the context and materials they need in hand
• Plan and manage travel end to end, including itineraries, logistics, and the details nobody notices until they are missing
• Serve as the first point of contact at the front of house, greeting guests, accepting deliveries, and making sure customers, candidates, and investors have a good first ten minutes
• Own the day-to-day running of the office, including stocked kitchen and supplies, grocery orders, and vendor relationships
• Coordinate our upcoming office move across vendors, building management, and the team
• Prepare correspondence, documents, and presentations, and submit and track expense reports
• Arrange team dinners, customer functions, and company events
• Take on ad hoc operations projects across the business as they come up
• Provide occasional light personal support, such as personal travel and reservations

Skills

Calendar management

Travel logistics

Communication

Discretion

Bias toward action

Tools

Google Workspace

Slack

Notion

Zoom

AI in admin

Job description

Flagler Health, Inc is building the clinical operating system for modern musculoskeletal care from their NYC base. This Executive Assistant role supports the CEO and CTO, keeping calendars tight, travel smooth, and the front of house welcoming for guests, investors, and candidates.

The successful candidate will be exceptionally organized, comfortable in a fast-moving startup environment, and will help run the upcoming office move, while coordinating cross-functional operations and events.