Systems Administrator – Tier 2 | Client-Facing, Project-Focused; MSP

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This range is provided by Bowman Williams. Your actual pay will be based on your skills and experience — talk with your recruiter to learn more.

$70,000.00/yr - $75,000.00/yr

Systems Administrator – Tier 2 | Client-Facing, Project-Focused (MSP)

Des Plaines, IL | Hybrid | Full-Time

Tired of being stuck on password resets?

Ready to finally use your skills on the kind of tech challenges that actually make you better at your job? We’re not your average MSP. Led by a dynamic, high-energy leadership team, we’ve built a company where technical growth, real problem-solving, and an open culture come standard. Our clients are mainly in the architecture, engineering, and construction space—meaning the problems are diverse, the projects are impactful, and the pace is fast (in the best way possible).

As a Tier 2 Systems Administrator, you’ll go beyond helpdesk tickets to handle client infrastructure, troubleshoot complex issues, implement cloud solutions, and play a key role in delivering top-tier IT experiences. If you're ready to move up, think critically, and actually enjoy what you do—you’ll thrive here.

What You’ll Be Doing

• Act as the escalation point for unresolved Tier 1 issues
• Troubleshoot and resolve advanced infrastructure issues across networks, servers, and cloud systems
• Configure and manage Microsoft 365 (Exchange, Intune, MFA, Conditional Access, SharePoint migrations)
• Maintain Active Directory, GPOs, DNS, DHCP, and VPN connectivity
• Perform hardware/software deployments and smooth data migrations
• Collaborate directly with clients—on-site and remote—to ensure satisfaction and clarity
• Join an on-call rotation (light and shared) for critical issue coverage
• Document systems and processes to elevate knowledge sharing across the team

What You Bring

• 5+ years of hands-on IT experience (at least 2+ in an MSP environment strongly preferred)
• Expert-level troubleshooting in Microsoft server/workstation environments
• Proficiency in Microsoft 365, Intune, SharePoint, Azure AD
• Familiarity with firewalls, site-to-site VPNs, endpoint security, and licensing management
• Experience with GPOs, AD Connect, DNS, DHCP, and MFA
• Client-facing confidence and communication skills—you can break down tech in plain English
• A proactive mindset—always looking for better solutions, not just fixes
• A reliable vehicle (you’ll visit clients in and around Des Plaines 2–3x/week)

What Makes This Role Different

• You won’t be stuck on entry-level tickets – we respect your time and skills
• You’ll work with the latest tools – no outdated tech stacks here
• You’ll grow fast – you’ll get project exposure and career support to level up
• You’ll be heard – our leadership wants your ideas, not just your output
• You’ll be part of a real team – collaborative, funny, supportive, and smart
• Hybrid work schedule – enjoy WFH flexibility plus in-person camaraderie
• Monthly team lunches & quarterly events – game nights, rooftop hangouts, and more
• Career development – we support certifications, training, and growth paths
• Open-door culture – your input and voice will shape how we grow
• Casual vibe, serious tech – think brainstorming over pizza, not silos and status meetings

If you're ready to grow your skills, be challenged, and actually enjoy your MSP job again—this is your shot.

• Seniority level
  
  Mid-Senior level

• Employment type
  
  Full-time

• Job function
  
  Information Technology
• Industries IT Services and IT Consulting

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Medical insurance

Vision insurance

401(k)

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