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

Bowman Williams; Des Plaines (IL); Hybrid; USD 70,000 - 75,000; Full time

Benefits offered by this job

Medical insurance

Vision insurance

401(k)

Job summary

Bowman Williams in Des Plaines, IL is seeking a mid-senior Systems Administrator (Tier 2) to join a client-facing, project-focused MSP. The role combines hands-on infrastructure work with cloud implementations and direct client interaction, offering strong technical growth in a fast-paced environment.

Ideal candidates have 5+ years of IT experience (MSP preferred), expertise in Microsoft 365, Intune, SharePoint, and Azure AD, and are comfortable visiting client sites 2–3 times per week.

Qualifications

• 5+ years of hands-on IT experience (MSP 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 communication skills and proactive problem-solving mindset
• Reliability for visiting clients in and around Des Plaines 2–3x/week

Responsibilities

• 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 data migrations
• Collaborate directly with clients—on-site and remote—to ensure satisfaction and clarity
• Join an on-call rotation for critical issue coverage
• Document systems and processes to elevate knowledge sharing across the team

Skills

Microsoft 365

Intune

SharePoint

Azure AD

Server troubleshooting

Active Directory

GPOs

DNS

DHCP

MFA

Firewalls

VPN

Client-facing

Problem solving

Drive to client sites

Job description

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

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

2 days ago Be among the first 25 applicants

Get AI-powered advice on this job and more exclusive features.

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.

Base pay range

$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

• Seniority level

  Mid-Senior level

Employment type

• Employment type

  Full-time

Job function

• Job function

  Information Technology

• Industries

  IT Services and IT Consulting

Referrals increase your chances of interviewing at Bowman Williams by 2x

Inferred from the description for this job

Medical insurance

Vision insurance

401(k)

Get notified when a new job is posted.

Sign in to set job alerts for “System Administrator” roles.

Chicago, IL $90,000.00-$110,000.00 1 week ago

Elk Grove Village, IL $80,000.00-$100,000.00 1 month ago

Systems Administrator ($80,000-$140,000)

Lisle, IL $38,894.07-$68,341.37 5 days ago

Elgin, IL $63,000.00-$73,000.00 1 month ago

Greater Chicago Area $120,000.00-$140,000.00 2 days ago

Chicago, IL $80,000.00-$140,000.00 4 days ago

Chicago, IL $80,000.00-$140,000.00 2 days ago

Chicago, IL $80,000.00-$130,000.00 4 days ago

Chicago, IL $120,000.00-$140,000.00 3 days ago

Chicago, IL $80,000.00-$140,000.00 4 days ago

Chicago, IL $80,000.00-$140,000.00 4 days ago

Chicago, IL $90,000.00-$95,000.00 3 days ago

Lisle, IL $42,661.58-$77,317.19 2 weeks ago

System Administrator (Level 2.5) – Hybrid

Arlington Heights, IL $80,000.00-$90,000.00 2 weeks ago

Chicago, IL $78,870.00-$103,191.00 4 days ago

Chicago, IL $80,000.00-$140,000.00 4 days ago

Des Plaines, IL $70,000.00-$75,000.00 4 days ago

Chicago, IL $101,920.00-$131,040.00 1 week ago

Chicago, IL $87,000.00-$111,000.00 2 weeks ago

Des Plaines, IL $65,000.00-$75,000.00 2 weeks ago

Discovery IT System Administrator (Top Secret Clearance Required)

Chicago, IL $124,895.40-$169,500.90 1 week ago

System Administrator (Managed Service Provider)

Des Plaines, IL $70,000.00-$80,000.00 5 days ago

Chicago, IL $76,000.00-$98,000.00 3 weeks ago

Chicago, IL $100,000.00-$140,000.00 4 days ago

Computer System Administrator - R10202203-5

Schaumburg, IL $75,000.00-$85,000.00 3 weeks ago

Systems Administrator - IT Operations Center

Chicago, IL $81,000.00-$90,000.00 1 week ago

Chicago, IL $90,000.00-$110,000.00 6 days ago

Systems Administrator - IT Operations Center

Warrenville, IL $81,000.00-$90,000.00 1 week ago

System Administrator (MSP | ConnectWise)

We’re unlocking community knowledge in a new way. Experts add insights directly into each article, started with the help of AI.