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Senior Service Desk Technician, Executive Support

Job in Chicago, Cook County, Illinois, 60601, USA
Listing for: Applied Systems
Full Time position
Listed on 2026-07-25
Job specializations:
  • IT/Tech
    IT Support, HelpDesk/Support, Technical Support
Job Description & How to Apply Below

Senior Service Desk Technician, Executive Support

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.

  • 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.

The best work happens when smart people move fast, together. For over 40+ years, Applied has built technology that solves real problems for insurance professionals - and we're still pushing what's possible.

You'll be part of our people-first culture built on trust, inclusion, and growth - where you're supported to deliver, collaborate with teammates who care, and grow with leaders invested in your success.

We invest in the whole person, not just the role. Our benefits and resources are built to support your health, your time, and your life outside of work:

  • Medical, Dental, and Vision Coverage
  • Holiday and Vacation Time
  • Health & Wellness Days
  • A Bonus Day for Your Birthday

Our targeted starting base salary in the United States for this position considers a variety of factors, including depth and breadth of experience, skills and role scope. Depending on the role, team members may also be eligible for additional compensation plans (bonus and commission).

Applied Systems is proud to be an Equal Employment Opportunity Employer. Diversity and Inclusion is a business imperative and is a part of building our brand and reputation. At Applied, we don't discriminate, and we are committed to recruit, develop, retain, and promote regardless of race, religion, color, national origin, sexual orientation, gender identity, disability, age, veteran status, and other protected status as required by applicable law.

Position Requirements
10+ Years work experience
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