Senior System Administrator (Managed Services Provider) | $110K–$120K | Chicago, IL

Are you a seasoned MSP professional who thrives in dynamic environments and wants real ownership of your work? We’re hiring a Senior System Administrator to join our team onsite in Chicago, supporting one of our most high-profile clients.

In this role, you’ll lead infrastructure projects, resolve high-level technical issues, and act as a trusted advisor to the client. If you’re hands-on, client-facing, and skilled in Azure, Microsoft 365, and Intune, this is a great opportunity to grow with a company that values your expertise.

Day to day:

  • Serve as the primary onsite engineer for a major client—owning the relationship and technical delivery
  • Design, deploy, and manage Azure infrastructure (VMs, identity, networking, storage)
  • Administer the full Microsoft 365 suite (Exchange, SharePoint, Teams, licensing)
  • Use Intune to manage endpoints, security policies, and device compliance
  • Tackle escalated support tickets across servers, networks, and cloud platforms
  • Contribute to IT strategy, implementations, and best practice improvements

Experience:

  • 2+ years of MSP experience across diverse client environments
  • Strong technical expertise in Azure, M365, Intune, and Windows Server
  • Proven ability to manage technical projects from planning to execution
  • Excellent communication and interpersonal skills—you’re calm under pressure and great with clients

Compensation:

  • $110,000–$120,000 annual salary
  • Health, dental, and vision insurance
  • 401(k) with company match
  • Company car and mileage reimbursement
  • Flexible scheduling and paid training
  • Certification reimbursement and career advancement opportunities