Bowman Williams
Tier 2 System Administrator (MSP) – Hybrid – Chicago, IL
A rapidly growing Managed Services Provider in the western Chicago suburbs is looking for a Tier 2 System Administrator to join their engineering team. This MSP has doubled its recurring revenue over the last 18 months and continues to grow aggressively and creating real advancement opportunities for someone who wants to move beyond traditional help desk work and into deeper systems, cloud, and virtualization responsibilities.
This is an environment built for people who take ownership, enjoy solving technical challenges end-to-end, and want to grow into a well-rounded systems engineer. You’ll work directly with senior engineers and tech leads, gain exposure to backend infrastructure, and support clients across diverse industries.
This role is hybrid: onsite in Lisle (60532) for the first 4–5 weeks of training, then 2 days onsite / 3 days remote.
Must have MSP experience.
What You’ll Do
Work Tier 2 tickets end-to-end with deeper troubleshooting across servers, cloud services, and critical infrastructure
Support Microsoft 365, including Exchange Online, Teams, SharePoint, and Entra ID configuration and administration
Manage Active Directory user administration, permissions, GPOs, and identity-related issues
Maintain and support virtualization environments (VMware, Hyper‑V)
Troubleshoot networking issues involving DHCP, DNS, VPNs, VLANs, and firewall appliances
Participate in project deployments: server builds, workstation refreshes, cloud migrations, and security implementations
Use PSA, RMM, and documentation platforms (Autotask, Datto RMM, ITGlue) to track and resolve issues
Act as a trusted escalation point for Tier 1 engineers
Collaborate with senior engineers while continuing to take on more complex work as your skill set grows
What We’re Looking For
2–4+ years of IT support experience, ideally within an MSP or multi‑client environment
Strong experience with Microsoft 365 administration (mailboxes, Teams policies, SharePoint, security settings, Entra ID)
Hands‑on experience with virtualization technologies (VMware required; Hyper‑V a plus)
Familiarity with Azure AD, basic Azure services, and hybrid identity concepts
Comfort working with firewalls and networking gear (WatchGuard, Barracuda, Aruba, etc.)
Understanding of servers, storage, backups, and general sysadmin fundamentals
Someone who doesn’t fold under pressure, takes initiative, and isn’t afraid to try to solve a problem before escalating
A team‑oriented, accountable engineer with strong communication skills
A self‑learner who enjoys continuous education, certifications, and building new skills
Why This Is a Strong Fit for a Tier 2 Who Wants More
High‑growth MSP environment with real exposure to backend infrastructure
Access to mentors who encourage learning rather than gatekeeping knowledge
A culture that promotes from within and rewards initiative
Target salary: $65,000–$80,000 based on experience
Medical, dental, and vision insurance
Telemedicine and legal assistance benefits
Short‑ and long‑term disability401(k) with company match
Certification bonuses & paid learning opportunities
Weekly meal benefit through DoorDash
Strong work‑life balance within a supportive, award‑winning team
Ready to Step Into a True Tier 2 / Sysadmin Path? If you’re a Level 2 engineer who wants to grow into a full systems role, get deeper into virtualization and Microsoft 365/Azure, and be part of a high‑growth MSP that actually invests in you, this is your next move.
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This is an environment built for people who take ownership, enjoy solving technical challenges end-to-end, and want to grow into a well-rounded systems engineer. You’ll work directly with senior engineers and tech leads, gain exposure to backend infrastructure, and support clients across diverse industries.
This role is hybrid: onsite in Lisle (60532) for the first 4–5 weeks of training, then 2 days onsite / 3 days remote.
Must have MSP experience.
What You’ll Do
Work Tier 2 tickets end-to-end with deeper troubleshooting across servers, cloud services, and critical infrastructure
Support Microsoft 365, including Exchange Online, Teams, SharePoint, and Entra ID configuration and administration
Manage Active Directory user administration, permissions, GPOs, and identity-related issues
Maintain and support virtualization environments (VMware, Hyper‑V)
Troubleshoot networking issues involving DHCP, DNS, VPNs, VLANs, and firewall appliances
Participate in project deployments: server builds, workstation refreshes, cloud migrations, and security implementations
Use PSA, RMM, and documentation platforms (Autotask, Datto RMM, ITGlue) to track and resolve issues
Act as a trusted escalation point for Tier 1 engineers
Collaborate with senior engineers while continuing to take on more complex work as your skill set grows
What We’re Looking For
2–4+ years of IT support experience, ideally within an MSP or multi‑client environment
Strong experience with Microsoft 365 administration (mailboxes, Teams policies, SharePoint, security settings, Entra ID)
Hands‑on experience with virtualization technologies (VMware required; Hyper‑V a plus)
Familiarity with Azure AD, basic Azure services, and hybrid identity concepts
Comfort working with firewalls and networking gear (WatchGuard, Barracuda, Aruba, etc.)
Understanding of servers, storage, backups, and general sysadmin fundamentals
Someone who doesn’t fold under pressure, takes initiative, and isn’t afraid to try to solve a problem before escalating
A team‑oriented, accountable engineer with strong communication skills
A self‑learner who enjoys continuous education, certifications, and building new skills
Why This Is a Strong Fit for a Tier 2 Who Wants More
High‑growth MSP environment with real exposure to backend infrastructure
Access to mentors who encourage learning rather than gatekeeping knowledge
A culture that promotes from within and rewards initiative
Target salary: $65,000–$80,000 based on experience
Medical, dental, and vision insurance
Telemedicine and legal assistance benefits
Short‑ and long‑term disability401(k) with company match
Certification bonuses & paid learning opportunities
Weekly meal benefit through DoorDash
Strong work‑life balance within a supportive, award‑winning team
Ready to Step Into a True Tier 2 / Sysadmin Path? If you’re a Level 2 engineer who wants to grow into a full systems role, get deeper into virtualization and Microsoft 365/Azure, and be part of a high‑growth MSP that actually invests in you, this is your next move.
#J-18808-Ljbffr