Director of IT

We need to produce HTML fragment with sections: About the role, Responsibilities, Requirements (maybe Qualifications), Skills? The posting includes sections: The Role (description), What You'll Do (responsibilities), Required Qualifications, Preferred Qualifications, Work Environment (maybe as Benefits? Actually it's about work environment). We need to follow rules: use

for section headings (e.g. About the role, Responsibilities, Requirements, Qualifications, Skills, Benefits, Pay, Schedule). We should include sections only when posting has real specific content. So we can have: - About the role (maybe from "The Role" paragraph) - Responsibilities (from "What You'll Do") - Requirements (maybe combine Required Qualifications) - Preferred Qualifications (maybe as Skills? But they said Skills heading optional; we could use Skills for preferred qualifications? Better to have a separate section for Preferred Qualifications but they didn't list that as allowed heading. Allowed headings list includes: About the role, Responsibilities, Requirements, Qualifications, Skills, Benefits, Pay, Schedule. So we can map Required Qualifications to Requirements or Qualifications. Preferred Qualifications could go under Skills. Work Environment maybe under Benefits? Not exactly. Could be omitted if not specific benefit. But we could include Work Environment as a section? Not in allowed list; we should not create new headings. So we need to fit content into allowed headings. Could put Work Environment under Benefits? Not accurate but maybe we can treat as Benefits? Or we could omit it if not specific benefit like pay, schedule. The instruction: "Prefer a few substantive sections over many thin ones." So we can include About the role, Responsibilities, Requirements (maybe combine Required and Preferred under Requirements?), Skills (maybe for preferred). Benefits maybe not present (no explicit benefits). Pay/Schedule not present, so omit. Thus sections:

About the role

... description ...

Responsibilities

• ... each bullet from What You'll Do ...

Requirements

• ... Required Qualifications bullets ...

Skills

• ... Preferred Qualifications bullets ...

We must not repeat job title. No Job ID. Remove boilerplate. Ensure we preserve all substantive information. Let's extract content. About the role paragraph: "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." We can condense but preserve all info. Should not invent. We'll keep as paragraph(s). Might split into two paragraphs for readability but still

. Responsibilities bullet list from "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 bullets: - 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 bullets: - 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 paragraph: "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." We could include this as a section maybe under Benefits? Not exactly. Could create a section "Work Environment" but not allowed. Perhaps we can incorporate into About the role or Responsibilities? Might be okay to add a section "Work Environment" but instruction says use headings from list; but also says "Use

for section headings (e.g. About the role, Responsibilities, Requirements, Qualifications, Skills, Benefits, Pay, Schedule)." The "e.g." suggests those are examples, not exclusive? It says "use

for section headings (e.g. About the role, Responsibilities, Requirements, Qualifications, Skills, Benefits, Pay, Schedule)." Likely they expect only those headings. Safer to stick to those. We could put Work Environment content under Benefits? Not accurate but maybe we can treat as Benefits (like work environment benefits). However they said never create Benefits section unless posting actually states them. The posting does state work environment and values, which could be considered benefits? Not exactly benefits like health insurance. Might be better to omit Work Environment section entirely, but we would lose substantive info. The instruction: "Preserve ALL substantive information; do NOT invent or summarize away detail." So we must keep it. We need a heading for it. Since allowed headings list includes Benefits, we could put work environment under Benefits. It's not a traditional benefit but it's still a section describing the work environment/values. Might be acceptable. Alternatively we could create a section "About the role" and include work environment there? But About the role already has description; we could append work environment paragraph there. That would preserve info without new heading. That seems better: keep About the role section with the initial description plus work environment and values. That way we don't need extra heading. Let's do that. Thus About the role paragraph(s) will include the initial description plus work environment and values. Now produce HTML:

About the role

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. 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. 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.

Responsibilities

• 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

Requirements

• 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