HealthSherpa - Director of IT

• 15+ years architecting, managing, and evolving IT environments, including MDM, secure SaaS administration and governance, identity, network, and cloud hosting in a Mac-centric environment • Proven experience owning an IT function end to end, including strategy, vendor and tooling decisions, and delivery • Deep experience operating IT and cloud environments under HIPAA/PHI and SOC 2 (HITRUST a plus), including closing findings and maintaining audit-ready documentation • Experience assessing and prioritizing technology risk and turning it into remediation plans leadership can act on • Experience hiring, developing, or leading IT staff, or readiness to build and lead a team • What We Offer (Full-time, Not Temporary/Not Seasonal) • Remote-first company (US-based remote only) • Great compensation package at a high-growth, profitable company • Excellent benefits package that includes health, vision, and dental coverage for you, your spouse, and dependents • HSA/FSA options with corresponding contribution limits • Monthly grocery stipend and home internet reimbursement • 401K w/ a match after a grace period • Life and AD&D coverage • Disability insurance (Short and Long Term) • Four (4) weeks of paid vacation in addition to paid holidays • Mental health and other wellbeing support programs through a partner network • As an organization, we value creating an inclusive and accessible experience. If you require reasonable accommodations during the application or interview process, please let your recruiter know. • We welcome and encourage people of diverse backgrounds, experiences, identities, abilities, and perspectives to apply. We are an equal-opportunity employer and a fun place to work. Come join the team at HealthSherpa!