Systems Administrator – MSP Escalations & Cloud

Overview

Systems Administrator – MSP Escalations & Cloud Support

Hybrid | West Suburbs of Chicago

$60,000 – $85,000

We’re a fast-growing Managed Service Provider (MSP) supporting small to mid-sized businesses throughout the Chicago suburbs. Our team is intentionally culture-forward, high-energy, and relationship-driven—this is a place where values actually matter, ownership is expected, and personalities are welcomed. We operate like a collaborative engineering shop rather than a rigid, corporate IT department, and we’re investing heavily in better tools, smarter processes, and long-term team growth.

This role is ideal for a strong Tier 2–level engineer who thrives in MSP environments, enjoys solving real problems end to end, and wants exposure to escalations and project work without being boxed into a silo.

Must-Have:
Prior MSP experience is required to move forward.

• Act as a true technical escalation point, owning complex issues from intake through resolution
• Troubleshoot across the Microsoft ecosystem, including Microsoft 365, Azure Entra , identity, access, and endpoint-related issues
• Administer and support Microsoft 365 environments, including Exchange Online, mail flow issues, shared mailboxes, permissions, and licensing
• Diagnose login, MFA, and access problems involving Conditional Access, device trust, and endpoint compliance
• Troubleshoot networking-related issues to identify root cause (endpoint vs network vs ISP vs Microsoft)
• Support and validate backup and recovery systems, assisting with restores when needed
• Document work thoroughly in Connect Wise PSA (or similar) with clean, professional ticket notes
• Contribute to project work (deployments, migrations, rollouts), including occasional onsite client visits
• Work collaboratively in a non-siloed MSP where everyone supports the queue and senior engineers help triage and guide

• Previous experience working at a Managed Service Provider (MSP)
• Strong troubleshooting skills across Microsoft 365, Azure Entra , Windows endpoints, and identity/access issues
• Hands-on experience with Exchange Online, mail flow troubleshooting, permissions, and licensing
• Working knowledge of Azure Entra , including users, groups, MFA issues, and Conditional Access basics
• 2+ years of experience with networking fundamentals (VLANs, switches, firewalls, routing concepts)
• Experience supporting Windows Server or server-adjacent infrastructure
• Familiarity with backups, endpoint security, VPN access issues
• Ability to work independently, own problems, and escalate appropriately with context
• Strong communication skills and comfort working directly with end users

• Intune (device enrollment, compliance, Bit Locker, endpoint troubleshooting)
• Prior experience in less-structured MSPs where autonomy is expected
• Relevant certifications (not required, but a plus)

This team values:

• Full ownership and accountability
• Strong customer instincts and follow-through
• Curiosity and a “student mentality”
• Big personalities who are collaborative, upbeat, and reliable
• Engineers who make good on promises and build trust naturally

This is a great environment for someone who knows what they’re doing, wants real responsibility, and enjoys being part of a tight-knit team—with the freedom to solve problems without excessive red tape.

• Salary: $60,000 – $85,000 (potential stretch for a strong 2.5-level engineer)
• Hybrid flexibility:
  Primarily remote with onsite client visits as needed (1–2x/week)
• Unlimited PTO (trust-based; typically after ~6 months)
• Dental & Vision: 100% employer-paid for employee
• Culture perks:
  Social, team-oriented environment with real camaraderie
• Growth runway:
  Exposure to escalations + projects with room to level up