System Administrator L2.5 (MSP)

Bowman Williams; Illinois; Hybrid; USD 80,000 - 90,000; Full time

Benefits offered by this job

Health Insurance

Dental Insurance

401(k) match

PTO 13 days

Holidays 7

Mileage reimbursement

Job summary

Bowman Williams is seeking a System Administrator T2.5 to support client environments across Microsoft cloud, Windows infrastructure, virtualization, networking, and escalated support.

You will handle advanced escalations, assist with project work, support Microsoft-focused initiatives, and help Tier 1 and Tier 2 technicians improve ticket quality and technical execution. This role offers hybrid work with local client visits in the Chicagoland area.

Qualifications

• 4+ years of MSP experience
• 4+ years of Tier 2/2.5 escalation experience across Microsoft, server, endpoint, cloud, and networking
• Hands-on with Microsoft 365, Azure, Entra ID, Intune, Windows Server, Active Directory, DNS, DHCP, and Windows 11

Responsibilities

• Handle Tier 2.5 escalations across Microsoft 365, Azure, Entra ID, Intune, Windows Server, AD, endpoints, networking, and client infrastructure
• Support Microsoft 365 administration, Exchange Online, SharePoint, OneDrive, Autopilot, Intune, Purview, and user access issues
• Troubleshoot Windows 11, Windows Server, DNS, DHCP, TCP/IP, printers, mobile devices, line of business apps
• Assist with Azure, Entra ID, security reviews, identity improvements, endpoint management
• Support VMware, Hyper‑V, vCloud Suite, patches, monitoring, backups
• Collaborate with clients before/during/after implementation; guide Tier 1/2 and improve escalation readiness
• Maintain detailed ticket notes, time entries, docs, processes, and client environment records
• Participate in occasional after-hours maintenance and on-call rotation

Skills

MSP experience

Tier 2.5 escalations

Microsoft 365

Azure

Entra ID

Intune

Windows Server

Active Directory

DNS

DHCP

VMware

Hyper-V

Backups

Patching

Monitoring

Hybrid infrastructure

Documentation

Service delivery

Client communication

Tools

PSA systems

Job description

Work Model: Hybrid WFH with local client visits as needed

Compensation: $80,000 - $90,000

MSP Experience: Required

We are a growing Managed Services Provider hiring a System Administrator T2.5 to support client environments across Microsoft cloud, Windows infrastructure, virtualization, networking, and escalated support.

This role is a strong fit for an MSP technician who has moved beyond standard Tier 2 support and is ready for deeper ownership across Microsoft 365, Azure, Entra ID, Intune, Windows Server, Active Directory, backups, and client infrastructure.

You will handle advanced escalations, assist with project based work, support Microsoft focused initiatives, and help Tier 1 and Tier 2 technicians improve ticket quality and technical execution.

Why MSP Candidates Apply

This is a strong step for someone who wants more than repetitive help desk work, but does not want to be oversold into a full senior architect role.

You will work across multiple client environments, support modern Microsoft cloud technologies, and gain exposure to project work involving cloud, security, endpoint management, infrastructure, and hybrid environments.

The company is continuing to grow its Managed Services, cloud, security, and hybrid infrastructure offerings, creating room for long term technical advancement.

Technical Scope

• Handle Tier 2.5 escalations across Microsoft 365, Azure, Entra ID, Intune, Windows Server, Active Directory, endpoints, networking, and client infrastructure
• Support Microsoft 365 administration, Exchange Online, SharePoint, OneDrive, Autopilot, Intune, Purview, and user access issues
• Troubleshoot Windows 11, Windows Server, DNS, DHCP, TCP/IP, printers, mobile devices, line of business applications, and general connectivity issues
• Assist with Azure, Entra ID, Microsoft security reviews, identity improvements, endpoint management, and cloud related updates
• Support VMware, Hyper V, vCloud Suite, VMware View, backups, patching, monitoring, and system optimization
• Work with clients before, during, and after implementation of new services, tools, and technical solutions
• Provide guidance to Tier 1 and Tier 2 technicians and help improve escalation readiness
• Maintain detailed ticket notes, time entries, documentation, internal processes, and client environment records
• Participate in occasional after hours maintenance and on call rotation

Required Background

• 4+ years of MSP experience supporting multiple client environments
• Strong Tier 2 or Tier 2.5 escalation experience across Microsoft, server, endpoint, cloud, and networking issues
• Hands on experience with Microsoft 365, Azure, Entra ID, Intune, Windows Server, Active Directory, DNS, DHCP, and Windows 11
• Working knowledge of VMware, Hyper V, backups, patching, monitoring, and hybrid infrastructure
• Experience with MSP tools, PSA systems, documentation standards, and service delivery processes
• Strong client communication, documentation, troubleshooting, and follow through
• Valid driver's license, reliable vehicle, smartphone, and ability to support local client needs in the Chicagoland area

Experience That Helps

• Azure, Microsoft, A+, Security+, Cisco, VMware, or similar certifications
• PowerShell or Python scripting exposure
• Experience supporting legal, healthcare, manufacturing, or other business applications
• Exposure to Microsoft security, compliance, Purview, or advanced Entra ID environments
• Health Insurance covered 100% for employee
• Dental Insurance covered 100% for employee
• 401(k) with 3% match
• 13 PTO days for sick or vacation time
• 7 customary holidays
• Mileage reimbursement for Chicagoland travel
• Growth and advancement opportunities as the company continues acquiring and expanding IT companies
• Opportunity to grow across Microsoft cloud, Azure, Intune, infrastructure, security, and advanced MSP escalations