Location: Chicago,Illinois,United States
The Tier 3 Technical Technician serves as the highest level of escalation within the service desk technical support structure, responsible for diagnosing and resolving complex infrastructure, system, and application issues. This role combines deep technical expertise with client-facing responsibilities, including a once weekly onsite support at a designated client location. The technician will act as a subject matter expert, mentor lower-tier support staff, and contribute to continuous improvement of IT operations.
Key Responsibilities:
Serve as the final escalation point for Tier 1 and Tier 2 support teams, resolving advanced technical issues across systems, networks, and applications
Perform root cause analysis on recurring incidents and implement long-term solutions
Provide onsite technical support at client location one day per week, including troubleshooting, maintenance, and relationship management
Implement, and maintain IT infrastructure components such as servers, networking equipment, and cloud environments
Collaborate with internal teams and client stakeholders to plan and execute IT projects and upgrades
Maintain detailed documentation for systems, processes, and issue resolutions
Monitor system performance and proactively address potential risks or inefficiencies
Assist in developing and enforcing IT standards, policies, and best practices
Mentor and provide guidance to Tier 1 and Tier 2 technicians
Participate in on-call rotation as needed for critical incident response
Required Qualifications:
5+ years of experience in IT support, with at least 2 years in a Tier 3 or senior technical role
Strong expertise in Windows Server, Active Directory, and Microsoft 365 environments
Advanced knowledge of networking concepts (DNS, DHCP, VLANs, VPNs, firewalls)
Experience with virtualization platforms (e.g., VMware, Hyper-V)
Familiarity with cloud platforms such as Azure
Proven ability to troubleshoot complex technical issues across multiple systems
Strong documentation and communication skills
Preferred Qualifications:
Industry certifications such as Microsoft (MCSE), Cisco (CCNA/CCNP), or CompTIA (Security+, Network+)
Experience working in a Managed Service Provider (MSP) environment
Scripting or automation experience (PowerShell preferred)
Exposure to cybersecurity tools and best practices
Soft Skills:
Strong problem-solving and analytical thinking
Ability to communicate technical concepts to non-technical stakeholders
High level of accountability and ownership
Customer-focused mindset with strong interpersonal skills
Ability to manage multiple priorities in a fast-paced environment
Work Environment:
Hybrid role with one scheduled onsite day per week at client location
Remaining work performed remotely
Occasional after-hours or weekend work may be required for maintenance or critical incidents
Partnering exclusively with law firms for over 30 years, Frontline Managed Services transforms operations by offering the only unified suite of AI-optimized, scalable managed services including: automated revenue cycle operations, proactive managed IT, GenAI Service Desk, and best-in-class Practice Management. For over 800 law firms, Frontline provides the operational backbone for efficiency, profitability, and growth.
