Senior Systems Administrator

Onni Group

Chicago, IL, USA
Base: $100,000 - $120,000 py; bonus/equity: not sp...
Tier 3 escalation and incident resolution
Microsoft 365 and windows server administration
Active directory / entra id management
GreyOwl is hiring a Senior Systems Administrator to serve as the technical escalation point for complex issues across managed clients and lead root-cause analysis while mentoring technicians

Job Summary

  • GreyOwl is hiring a Senior Systems Administrator to serve as the technical escalation point for complex issues across managed clients and lead root-cause analysis while mentoring technicians.
  • The role offers competitive pay, health savings accounts, an annual education allowance, a generous referral program, and a fun, collaborative company culture with team-building events.
  • Employees are expected to use AI tools responsibly in compliance with company policies and disclose AI usage in their work.

Matching Summary

GreyOwl is hiring a Senior Systems Administrator to serve as the technical escalation point for complex issues across managed clients and lead root-cause analysis while mentoring technicians.

Salary

Base: $100,000 - $120,000 per year; Bonus/Equity: Not specified; Benefits: Health Saving Account, Flexible Saving Account, Employee Assistance Program, Annual Education Allowance, Generous Referral Program

Skills & Requirements

Must-have

  • Tier 3 escalation and incident resolution
  • Microsoft 365 and Windows Server administration
  • Active Directory / Entra ID management
  • Networking fundamentals including TCP/IP and VPN
  • Virtualization with VMware or Hyper-V
  • PowerShell scripting and automation mindset
  • Client-facing professionalism and communication

Nice-to-have

  • Mentorship and team collaboration
  • Process improvement and automation
  • Participation in after-hours escalation rotation
  • Fun and collaborative company culture
  • Use of AI tools responsibly

Key Requirements

  • 5+ years IT support experience
  • Significant Tier 3 or Senior SysAdmin role experience
  • MSP experience strongly preferred
  • Strong troubleshooting in Microsoft-centric environments
  • Experience with virtualization and backup/DR concepts
  • Strong written communication skills

Work Rights

Not specified

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