Director of IT

HealthSherpa

Remote regions

US

Salary range

$192,000–$250,000/yr

Benefits

4w PTO

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About the Role:

  • Serve as principal authority on IT, setting strategy and owning outcomes.
  • Build and lead the IT team as scope grows.
  • Report to VP Engineering and partner with Security, Engineering, Operations, and Legal.

You Will:

  • Architect and steward SaaS, identity, network, cloud hosting, and Mac-centric fleet.
  • Establish IT standards, policies, and governance aligned with HIPAA/PHI and SOC 2.
  • Own risk assessment and partner with Security on controls and audit readiness.

You Have:

  • 15+ years architecting and managing IT environments in a Mac-centric environment.
  • Deep experience with HIPAA/PHI and SOC 2 compliance.
  • Experience hiring, developing, or leading IT staff.

What We Offer:

  • Remote-first company with US-based remote only.
  • Competitive compensation, equity, and excellent benefits.
  • Four weeks of paid vacation, parental leave, and mental health support.

HealthSherpa

HealthSherpa is a healthcare startup helping people find and enroll in individual health coverage, having helped over 20 million people. The company is a fully remote, mission-driven team of 230 employees focused on making ACA coverage accessible.

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