Help Desk Specialist

Job Title: Help Desk Specialist

Location: Wheeling, IL

About George J. Priester Aviation

George J. Priester Aviation is a premier aviation services company providing comprehensive aircraft management, charter, maintenance, and flight operations solutions. With decades of experience supporting owner-managed and client-focused flight departments, we are known for our commitment to safety, professionalism, and white-glove service.

Our team operates in a dynamic Part 135 and Part 91 environment, supporting diverse aircraft types and mission profiles across the U.S. and internationally. At George J. Priester Aviation, we value integrity, collaboration, and accountability and we take pride in building long-term careers within aviation.

Position Summary:

The Help Desk Specialist provides Tier 1-2 technical support across a mixed Windows, macOS, and mobile environment. This role requires strong experience with Freshservice as the primary ITSM platform, along with hands-on skills in Microsoft Entra ID, Intune, Autopilot, and iPad MDM solutions including MaaS360 and Jamf. This individual is customer-focused, detail-oriented, and comfortable supporting a wide range of technologies.

Key Responsibilities

IT Service Management (Mandatory)

Use Freshservice as the primary ticketing and workflow platform.
Triage, prioritize, and resolve incidents and service requests within SLA.
Maintain accurate ticket documentation, asset records, and knowledge base articles.

End-User Support

Provide technical support for Windows 11, macOS, and iPad devices.
Troubleshoot hardware, software, printing, and peripheral issues.
Provision iPads, and notebooks to new hires.
Perform application installs, updates, and configuration.
Deliver support both remotely and onsite with excellent customer service.

Identity & Access Management

Manage user accounts, groups, and access policies in Microsoft Entra ID.
Support MFA, SSO, conditional access, and password resets.
Handle onboarding/offboarding workflows and identity lifecycle tasks.

Device Management & Provisioning

Deploy and manage Windows devices using Intune and Windows Autopilot.
Configure compliance policies, configuration profiles, and security baselines.

Mobile Device Management (MDM)

Enroll, configure, and support iPads & BYOD smartphones through MDM platforms
- (MaaS360, Jamf).
Apply app deployments, restrictions, compliance rules, and remote actions (wipe/lock).
Maintain accurate device inventory and ensure security compliance.

Networking & Connectivity

Assist with troubleshoot LAN, and WLAN/Wi-Fi issues.
Assist with monitor and support network infrastructure using Cisco Meraki dashboards.

System Administration

Perform OS updates, patching, and endpoint security tasks.
Support Microsoft 365 applications and Exchange Online cloud services.
Assist with hardware lifecycle management and asset tracking.

Documentation & Collaboration

Create and maintain technical documentation and knowledge base articles.
Collaborate with engineers/manager/MSP on escalations and project work.
Communicate clearly and professionally with end users and team members.

Required Skills & Experience

Mandatory: At least 3 years’ experience using Freshservice for ticketing, asset management, and workflows.
Mandatory: At least 3 years’ experience with MDM for iPads, including MaaS360 and or Jamf.
CompTIA A+, Network+, or Microsoft Cloud certifications.
- Equivalent practical experience will be considered in lieu of certifications.
Hands-on experience with Microsoft Entra ID, Intune/Autopilot, and Exchange Online.
Proficiency with Windows 11 and macOS troubleshooting.
Basic understanding of networking fundamentals (DNS, DHCP, TCP/IP, VPN).
Ability to be on call for minimal after-hours support.
Excellent communication, customer service, and problem-solving skills.
Experience with ITIL-aligned processes and service management best practices.

Preferred Qualifications

Experience with Apple Business Manager and Jamf.
Scripting familiarity (PowerShell/Bash).
Experience in fast-paced helpdesk environments.
Familiarity with Dell notebooks, and Apple iPads.

Compensation & Benefits

George J. Priester Aviation offers a competitive total rewards package designed to support the health, financial security, and well-being of our team members, including:

Health & Wellness

Medical coverage (PPO and High Deductible plans) through Blue Cross Blue Shield
Dental and vision coverage
Company-paid short-term and long-term disability insurance
Company-paid basic life and AD&D insurance, with optional supplemental coverage
Voluntary accident, critical illness, and hospital indemnity plans

Financial & Retirement

401(k) retirement plan with company match
Annual company-funded profit-sharing contribution
Health Savings Account (HSA), Flexible Spending Accounts (FSA), and Dependent Care FSA options

Time Off & Work-Life Balance

Paid company holidays
Unlimited Paid Time Off (PTO), subject to scheduling guidelines
Sick leave in accordance with company policy

Additional Benefits

Tuition reimbursement program
Company-paid legal services and identity theft protection
Company-paid pet insurance for dogs or cats
Employee assistance and support resources

Benefits eligibility and offerings may vary based on role, employment type, and client program.

Work Environment

This position operates in a fast-paced aviation environment that may include travel, variable schedules, and close coordination with flight crews, maintenance teams, and client representatives.

Equal Opportunity Employer

George J. Priester Aviation is an Equal Opportunity Employer and is committed to fostering an inclusive workplace. We do not discriminate based on race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, veteran status, or any other protected status.

How to Apply:

If you are ready to take your career to the next level and meet the qualifications for this role, we invite you to apply. Please submit your resume detailing your experience and why you are an excellent fit for this position.

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