Senior Service Desk Lead - Executive Support (Hybrid)

IVANS Insurance Solutions; Chicago (IL); Hybrid; USD 60,000 - 85,000; Full time

Benefits offered by this job

Medical, Dental, and Vision Coverage

Holiday and Vacation Time

Health & Wellness Days

Bonus Day for Your Birthday

Job summary

Applied Systems in Chicago seeks a Senior Service Desk Technician to lead complex L2 incidents and mentor staff within Corporate IT. You’ll manage escalations, improve processes, and maintain deep knowledge of end-user systems, including Intune and GPOs.

The role blends technical leadership with on-site collaboration at the Chicago Fulton Market office, with on-call duties and ITIL-aligned daily work. Equal opportunity employer.

Qualifications

• Minimum of 3–5 years in an enterprise Service Desk environment.
• Proven experience acting as a team lead, senior technician, or primary escalation point.
• Strong technical knowledge of Windows, macOS, Active Directory, Azure AD, GPOs and endpoint management tools.
• Significant experience with IT Service Management platforms and reporting.
• Strong understanding of ITIL framework variants (Incident, Problem, Knowledge).
• Excellent attention to detail with analytical, trend‑analysis and problem‑solving abilities.
• Ability to prioritize and execute tasks under stress.
• Strong written and verbal communication, mentoring ability, BS degree or equivalent.

Responsibilities

• Acts as the primary technical escalation point for complex incidents and requests.
• Identify, prioritize, and confirm resolutions for recurring issues (Problem Management).
• Mentor, coach, and train junior staff as technical lead and quality check.
• Builds deep knowledge of end-user systems to resolve advanced issues (GPOs, Intune, registry).
• Analyze ticket data to identify systemic issues and drive process improvements.
• Maintain the Service Desk knowledge base and ensure accurate documentation.
• Assist the Service Desk Manager with reporting, metrics, and QA checks.
• Coordinate with L2/L3 teams during major incidents as liaison.
• Perform on-call duties for after-hours escalations.
• Apply ITIL concepts to daily operations and propose improvements.

Skills

Team leadership

Mentoring

Communication

Analytical thinking

Prioritization under stress

Problem solving

Windows

macOS

Active Directory

Azure AD

GPOs

Intune

Kandji

ITIL knowledge

ITSM experience

Education

BS Degree or Equivalent experience

Tools

Intune

Kandji

ITSM platforms

Job description

Applied Systems in Chicago seeks a Senior Service Desk Technician to lead complex L2 incidents and mentor staff within Corporate IT. You’ll manage escalations, improve processes, and maintain deep knowledge of end-user systems, including Intune and GPOs.

The role blends technical leadership with on-site collaboration at the Chicago Fulton Market office, with on-call duties and ITIL-aligned daily work. Equal opportunity employer.