IT Support Specialist

Iterative Health is seeking a skilled and dependable IT Support Specialist to provide end-user and systems support across multiple sites. This role will report directly to the Sr. IT Systems Administrator and will serve as a key IT resource supporting a growing organization of approximately 300 users.

This position is ideal for a hands-on IT professional who combines strong technical troubleshooting ability with  clear, confident communication — especially when supporting VIP stakeholders and addressing cybersecurity and compliance needs (SOC 2, PHI handling).

• Provide Tier 1 / Tier 2 support for Windows and macOS users in a hybrid environment.
• Troubleshoot and resolve issues across hardware, operating systems, SaaS applications, security tools, and connectivity.
• Provide professional, high-touch support to all user levels, including executives and external key opinion leaders.m.
• Provide remote support using Splashtop, plus phone/chat/video and in-person support as needed.
• Support conference rooms and AV / meeting technology as needed.
  
  

• Own end-user onboarding/offboarding workflows including:
  
  
• Laptop provisioning
• Account creation / deprovisioning
• Software deployment
• Access requests and approvals
  
  
• Provision and manage users and access in:
  
  
• Microsoft 365
  
• Google Workspace
  
• Okta
  
• Microsoft Entra ID
  
  
• Maintain documentation and ensure procedures are consistent and auditable.
  
  

• Administer and support endpoint management systems including:
  
  
• Microsoft Intune
  
• Kandji
  
• Windows Autopilot
  
• Apple Business Manager
  
  
• Support endpoint security tooling such as Microsoft Defender and Bitdefender.
• Track, manage, and maintain endpoint inventory lifecycle (procurement, configuration, deployment, repairs, replacements).

• Work within ITSM ticketing systems (Freshservice and/or Jira) to track, resolve, and document support activities.
• Create and maintain Knowledge Base (KB) documentation and user-facing guides.
• Contribute to continuous improvement of IT workflows and service delivery.
  
  

• User directory audit and access validation (M365/Google/Okta/Entra)
• Endpoint inventory audit and lifecycle controls
• Creation and improvement of KB articles and internal IT documentation
• Supporting integrations or company expansion initiatives (including multi-site support)
  
  

• 5+ years of hands-on IT support experience (Tier 1/Tier 2)
• Experience supporting both Windows and macOS environments
• Strong experience with remote support tools and workflows
• Professional experience with:
• Microsoft 365 administration
  
• Okta administration
  
• Microsoft Entra ID
  
• Strong troubleshooting skills: able to isolate issues quickly and escalate appropriately
• Excellent communication skills, especially in high-pressure / high-urgency situations
  
  

• Scripting or programming experience (PowerShell, Python, etc.)
• Experience conducting security audits, access reviews, and systems compliance checks
• Experience supporting healthcare/clinical environments involving PHI
• Experience supporting multi-site organizations and integrating systems/processes during growth
  
  

• Bachelor’s degree preferred, or equivalent professional IT experience
• Microsoft certifications such as MS-900 or MD-102
• ITIL Foundation
• Okta Certified Professional
  
  

A successful IT Support Engineer at Iterative Health will:

• Deliver consistent, reliable support outcomes
• Communicate clearly with stakeholders (especially VIP users)
• Proactively document systems and support procedures
• Contribute to measurable improvements in security, endpoint management, and user onboarding quality
• Be dependable and accurate — matching confidence with real capability