[Hiring] IT Systems Administrator @Medely

Role Description

Medely's IT team is small, high-leverage, and remote-first. We support a distributed workforce on a modern SaaS stack including, but not limited to, Okta, Google Workspace, Slack, Zoom and Zoom Phone, Notion, our ticketing platform (Medely Help), Iru MDM, Rippling, Ashby, Torii, and dozens of business apps. Day-to-day support volume is modest and well-documented; most of this role's time goes to building, securing, and automating the systems underneath.

This role is a hybrid:

• Hands-on IT generalist (the occasional password/MFA reset, break/fix, or machine swap, plus the employee lifecycle)
• IT Systems Administrator (owner of identity, device, and SaaS architecture)
• Automation architect (the person who turns repeated work into workflows, APIs, and safe AI-assisted processes), all with a security-first mindset.

You'll be the engineer who makes access control automatic, auditable, and least-privilege by default, and who makes IT's operational data clean enough to measure, report on, and automate against.

Qualifications

• 4+ years in IT operations / systems administration / IT engineering in a SaaS-first, remote company
• Deep, hands-on Okta administration: SSO (SAML/OIDC), SCIM, group rules, attribute mapping, authentication policies, Device Trust, and Okta Workflows
• Hands-on MDM for both macOS and Windows (Iru/Kandji, Jamf, and/or Intune), including ABM/ADE, Autopilot, compliance policies, and app deployment
• Genuinely comfortable supporting both macOS and Windows
• Microsoft 365 / Office 365 experience: licensing and app deployment (Word, Excel, PowerPoint, Outlook), Entra ID basics, coexistence with Google Workspace, and supporting Office apps on both macOS and Windows
• Proven experience building automations and integrations with n8n (strongly preferred), Okta Workflows, Zapier/Make, or Workato — using REST APIs, webhooks, and JSON
• Core competency: building with AI in a governed way.
• Strong understanding of least privilege, RBAC, joiner/mover/leaver processes, and SOC 2–aligned IT controls
• Proven partnership with HR / People Ops on employee lifecycle management
• Hands-on 1Password admin experience (Business or Enterprise)
• A security-minded approach: comfortable reading auth logs, spotting risky configurations, and pushing back when convenience would weaken a control
• Experience with SaaS management / shadow IT discovery (Torii, Productiv, Zluri, or similar)
• Google Workspace administration experience
• Hands-on Zoom and Zoom Phone administration experience
• Advanced experience administering ticketing platforms
• Technical translator, in both directions
• Clear writer: produces runbooks, KB articles, and decision docs
• Reliable owner: keeps work visible, meets deadlines, raises blockers early
• Self-starter with a real appetite for technical growth

Requirements

• Okta Certified Professional (strongly preferred)
• Okta Certified Administrator (Okta Certified Consultant / Workflows a plus)
• Notion certification (Notion Admin / Notion Essentials or equivalent)
• Apple Certified Support Professional / Apple Deployment and Management (nice to have)
• Microsoft Endpoint Administrator (MD-102) or equivalent Intune certification (nice to have)
• Jamf or Kandji/Iru certification (nice to have)
• Google Workspace Administrator certification (nice to have)
• Zoom Phone or Zoom Workplace admin training/certification (nice to have)
• Security fundamentals (CompTIA Security+, or similar) (nice to have)

Benefits

• Competitive Compensation: Based on experience and performance
• Long-term Incentives: 401k
• Healthcare Benefits: Full suite of benefits including medical, dental, and vision insurance
• Flexibility: Flexible and unlimited PTO
• Paid parental leave
• Purpose: Join a growing mission-oriented startup that is modernizing the healthcare industry nationally!
• Ownership: Drive meaningful business impact on a team you’ll help build and define!
• Remote: Work in a digital environment with all the tools to achieve your work as though you were in the office!