Senior Service Desk Technician, Executive Support

Applied Systems•Chicago, IL

14h•$60,000 - $85,000•Hybrid

About The Position

Applied is where insurance technology gets reinvented, and we build it fast. Our cloud software and AI-powered solutions reach thousands of agencies and brokers worldwide, setting the pace for what modern insurance can do. We’re looking for a Senior Service Desk Technician, Executive Support to join our Corporate IT team. The Senior Service Desk Technician serves as a technical lead and primary escalation point for the Service Desk team. This role is responsible for handling complex L2 incidents, mentoring junior technicians, and driving process improvements within the Service Desk. In this blended technical and leadership role, the ability to analyze trends, manage escalations, and mentor others is key to being successful. For the "Chicago Office" specific tasks for the role: Serves as the dedicated onsite IT technician and primary point of contact for the Applied Systems Chicago Fulton Market office, supporting our executive-level users. Independently manage a complex onsite environment while building and maintaining strong relationships with the office and building property management contacts and assisting with facilities-related IT matters and vendor coordination. Manage a full spectrum of IT support needs for the Chicago office population, providing hands-on support across all hardware, software, network, and access control needs. Maintain IT hardware inventory for provisioning/shipping for break-fix needs as well as arranging hardware recovery.

Requirements

Minimum of 3-5 years of experience 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 (e.g., Intune, Kandji).
Significant experience with IT Service Management (ITSM) platforms, including reporting and dashboarding.
Strong understanding of the ITIL framework, particularly Incident, Problem, and Knowledge Management.
Keen attention to detail with strong analytical, trend-analysis, and problem-solving abilities.
Ability to effectively prioritize and execute tasks under stress.
Strong written and oral communication skills, with a proven ability to mentor and guide junior team members.
BS Degree or Equivalent experience

Nice To Haves

ITIL Foundations, CompTIA A+, and/or Security+ strongly preferred.
Microsoft 365 Certified: Endpoint Administrator Associate is a plus

Responsibilities

Acts as the primary technical escalation point for complex incidents and service requests from L1 Service Desk Technicians.
Responsible for identifying, prioritizing, and confirming problem resolutions for recurring issues (Problem Management).
Mentors, coaches, and provides on-the-job training to junior Service Desk staff, acting as a technical lead and quality check.
Builds and maintains in-depth technical knowledge of end-user systems to effectively resolve L2 issues (e.g., advanced GPO, Intune, or registry troubleshooting).
Analyzes ticket data and trends to identify systemic issues, knowledge gaps, and opportunities for process improvement or automation.
Manages and curates the Service Desk knowledge base, ensuring all technical documentation is accurate, up-to-date, and easy to understand.
Assists the Service Desk Manager with reporting, metrics analysis, and quality assurance checks on tickets.
Coordinates with L2/L3 teams (Infrastructure, Desktop, Network, etc.) during major incidents, acting as a communication liaison to the Service Desk.
Performs on-call duties on a rotation basis for after-hours escalations.
Maintains a thorough understanding of ITIL principles (Incident, Problem, Change, Knowledge) and applies them to daily work.
Presents recommendations for service improvements to management in a structured and understandable manner.
Serves as the dedicated onsite IT technician and primary point of contact for the Applied Systems Chicago Fulton Market office, supporting our executive-level users.
Independently manage a complex onsite environment while building and maintaining strong relationships with the office and building property management contacts and assisting with facilities-related IT matters and vendor coordination.
Manage a full spectrum of IT support needs for the Chicago office population, providing hands-on support across all hardware, software, network, and access control needs.
Maintain IT hardware inventory for provisioning/shipping for break-fix needs as well as arranging hardware recovery.