Senior Service Desk Technician, Executive Support

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

Job Description

ICIMS Default: Senior Service Desk Technician, Executive Support

ICIMS Default: Chicago, IL

Team: Corporate IT

Salary Range: USD 60,000- USD 85,000

Location: Chicago, IL

LOCATION: This position operates in a hybrid model with regular in-office collaboration days from our Chicago office.

Opportunity for Impact

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.

What You’ll Do

• 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.

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.

What We’re Looking For:

• 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

Bonus points if you also have:

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

Talent shows up in a lot of different ways, and we mean that.

We welcome candidates from all backgrounds and experience levels, including military members and their spouses and those without a traditional degree or tech background.

Why You’ll Like Working on Team Applied

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.

How We’ll Support You

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

Compensation Transparency

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).

Your Security Matters:

Our candidates’ personal information and online safety are top of mind. Applied communicates with candidates only via a secure @appliedsystems.com email address or through our official careers portal. Recruiters will never request payments or ask for financial account or sensitive personal information like Social Security numbers.

AI Utilization

We leverage AI tools to streamline parts of our recruitment workflow (such as resume parsing and interview scheduling). However, final decisions are always conducted by real humans.

EEO Statement

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.

#LI-US