Director of IT

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 our first Director of IT to own how Flagler runs internally: identity, devices, networks, and the security controls underneath them across our New York HQ and the India entity we're standing up over the next year.
The two sides of the company won't run the same stack. New York is Google Workspace and Macs. The India entity is being built on Microsoft - Entra ID, Intune, and Windows endpoints and that is where most of the build work sits.
Today this work is spread across engineering and operations. You'll take it over end to end. You'll report to our CTO and partner closely with Finance, People Ops, and Engineering.
This is a hands-on role. You'll set the strategy and also write the Intune policy, run the access review, and be there when the new office gets cabled.
What You'll Do

• Own corporate IT across two stacks: Microsoft 365 and Entra ID in India, Google Workspace in New York

• Build and run the India Windows fleet on Intune, with Autopilot provisioning from day one

• Stand up IT for our India entity: procurement, connectivity, and Conditional Access into US systems

• Run onboarding and offboarding in both directories, from day-one setup to same-day de-provisioning

• Hire and manage an in-country IT lead once the India team is large enough

• Build the physical layer for our office move: network, Wi-Fi, and conference room AV

• Define the support model: ticketing, response targets, and runbooks across two countries

Required Qualifications

• 7+ years in corporate IT, including 2+ owning the function or leading a team

• Deep hands-on Microsoft administration: Entra ID, Intune, Microsoft 365, and Windows endpoints at scale

• Comfortable running Google Workspace and a macOS fleet alongside it

• Built an IT function from a thin base at a high-growth company

• Experience supporting employees or contractors outside the US

• Owned office infrastructure through a build-out or move: network, Wi-Fi, AV

• Vendor and budget ownership, including Microsoft licensing and renewals

• Able to work from our New York office on a regular in-person basis

Preferred Qualifications

• Stood up a Microsoft tenant for a new international entity, particularly in India

• Used Windows 365 or Azure Virtual Desktop to keep company data off offshore endpoints

• Healthcare experience handling PHI, BAAs, and clinical or revenue cycle access patterns

• Automation habit: PowerShell, Microsoft Graph, Power Automate, or equivalent

• Used AI tooling to take work off the IT queue

• Hired or managed an outsourced IT provider

• Microsoft certification (MD-102, SC-300, AZ-104) or equivalent depth

Work Environment

• This role requires regular and consistent in-person collaboration from our New York office.

• We maintain a highly collaborative culture with video-on team meetings and technical discussions.

• Expect occasional travel to India as that entity comes online.

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.