Senior Systems Administrator (Founding IT Team)

Full-time · Remote (US)
Compensation: $100,000–$150,000 base + competitive equity
Visa sponsorship: Not available

About the Role

We’re hiring two Senior Systems Administrators (7+ years) to help scale internal IT from ~500 to ~2,500 employees over the next phase of growth. You’ll be a foundational member of a newly formed internal IT team, owning core systems that support a distributed, healthcare-focused workforce across the U.S.

This is a hands-on, high-ownership role for someone who enjoys building from first principles, operating with low ego, and solving ambiguous problems in a fast-moving environment.

What You’ll Do

• Architect, deploy, and operate core IT infrastructure with a heavy focus on Microsoft 365, Entra ID (Azure AD), and Intune
• Lead IT integrations for acquired companies, including decommissioning legacy systems and migrating users, devices, and data
• Own and continuously improve the security posture across endpoints, identity, and networks
• Manage endpoints for a fully distributed workforce (Windows, macOS, mobile) using modern MDM and security tooling
• Standardize device configurations, access controls, and security policies at scale
• Build repeatable IT integration playbooks to support an aggressive M&A roadmap
• Partner cross-functionally with leadership, security, and operations teams

What We’re Looking For

• 7+ years of experience in enterprise systems administration
• Deep hands-on expertise with Microsoft 365 environments
• Strong experience with identity, endpoint management, and security
• Comfort operating in high-growth, imperfect environments
• Proven ability to own problems end-to-end with minimal guidance
• Experience supporting distributed or remote-first teams is a strong plus
• Prior M&A or large-scale migration experience is a plus

Tech Stack

• Microsoft 365
• Entra ID (Azure AD)
• Intune

Remote Policy

• US-based remote, excluding Hawaii and Alaska (time zone constraints)

Why This Role

• Founding member of an internal IT function—not inheriting legacy chaos
• Direct ownership over systems that materially impact patient care
• Meaningful equity upside
• Mission-driven company using AI to fundamentally change healthcare delivery

Interview Process

1. Hiring Manager interview (Head of Business Operations)
2. Technical interview
3. Final interview with CEO