Executive Assistant

Flagler Health is building the clinical operating system for modern musculoskeletal care.

We partner with MSK provider groups and specialty clinics to help them grow, operate more efficiently, and deliver better longitudinal care across patient acquisition, clinical workflows, and ongoing patient engagement. Our platform sits at the intersection of care delivery and clinic operations, helping providers capture more value across the full patient lifecycle.

We’ve recently raised our Series B and are entering our next phase of growth.

The Role:

We're hiring an Executive Assistant to support our CEO and CTO and to keep the office running. This is a genuinely broad role: some of your week is high-stakes calendar and travel work for two founders, and some of it is making sure the fridge is stocked before a customer walks in. Both matter, and we'd rather be honest about that up front.

You'll be the first person guests meet, the person who makes sure the founders are prepared before they walk into a room, and the person who quietly owns the dozen operational things that would otherwise land on someone who should be building product. You'll also help run our upcoming office move.

This role suits someone early-to-mid career who is exceptionally organized, moves fast, and would rather own a problem than escalate it. You'll work closely with our Chief of Staff.

What You’ll Do:

• 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

Required 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 escalate 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.

Preferred Qualifications:

• Experience supporting more than one executive at the same time

• Experience planning or executing an office move

• Experience using generative AI and automation in an administrative setting

Work Environment:

• Five days a week, in person, at our NYC office

• You will work directly with the CEO, CTO, and Chief of Staff

Our Values:

This is what you can expect of your teammates at Flagler:

• Owner: We own our work like founders. We don't wait to be asked, and we pick up the problem nobody else has.

• Builder: We like making things from scratch. We don't need a playbook to start, and we'd rather ship a rough first version than wait on a perfect spec.

• Fast: We make quick decisions. We favor progress and respect process.

• Transparent: We communicate directly. We value merit and honesty, and we challenge assumptions, including our own.

• Curious: We explore new approaches and ask "why" often.