System Administrator

Priester Holdings; Wheeling (IL); On-site; USD 80,000 - 90,000; Full time

Benefits offered by this job

Medical coverage (PPO)

Dental and vision coverage

Disability insurance

Life insurance

401(k) company match

HSA and FSA options

Unlimited PTO

Tuition reimbursement

Pet insurance

Job summary

George J. Priester Aviation is seeking a Systems Administrator to manage a 100% cloud-based IT environment in Wheeling, IL.

The role emphasizes Entra ID, Intune/Autopilot, Exchange Online, and Defender, with Meraki network responsibilities and 1st/2nd line support for end users. Ideal candidates will have 5+ years in ticketing and IT helpdesk, strong MDM experience (MaaS360/Jamf), and solid networking knowledge.

Qualifications

• At least 5 years' experience with ticketing systems.
• At least 3 years' experience with MDM for iPads (MaaS360 or Jamf).
• Certifications: CompTIA A+, Network+ or Microsoft Cloud.
• Hands-on experience with Microsoft Entra ID, Intune/Autopilot, and Exchange Online.
• Proficiency with Windows 11 and macOS troubleshooting.
• Networking fundamentals (DNS, DHCP, TCP/IP, VPN, VLAN, WLAN).
• On-call availability with weekly rotation.
• Excellent communication and customer service.

Responsibilities

• 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.
• 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.
• 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.
• Deploy and manage Windows devices using Intune/Autopilot.
• Configure compliance policies, configuration profiles, and security baselines.
• Enroll, configure, and support iPads through MDM platforms: MaaS360, Jamf.
• Apply app deployments, restrictions, compliance rules, and remote actions.
• Maintain accurate inventory and ensure security compliance.
• 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.

Skills

Entra ID

Intune/Autopilot

Exchange Online

Microsoft Defender

MDM MaaS360/Jamf

Ticketing systems

Windows 11 troubleshooting

Networking basics

Education

CompTIA A+/Network+ or Microsoft Cloud certifications

Tools

Cisco Meraki

MaaS360

Jamf

Freshservice

Job description

Job Details

Job Location: WHEELING, IL 60090

Salary Range: $80,000.00 - $90,000.00 Salary/year

Job Title: System Administrator

Location: Wheeling, IL (Chicagoland area)

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.

Overview

The Systems Administrator requires hands-on skills in Microsoft Entra ID, Intune/Autopilot, Exchange Online, and Microsoft Defender in a 100% fully cloud managed environment. No on-premise servers. This position also requires Meraki network experience and tier 1/tier 2 helpdesk responsibilities. The ideal candidate is customer-focused, detail-oriented, and comfortable supporting a wide range of technologies.

Key Responsibilities

IT Service Management

• 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/Autopilot.
• Configure compliance policies, configuration profiles, and security baselines.

Mobile Device Management (MDM)

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

Networking & Connectivity

• Manage our existing Cisco Meraki environment:
• Support Meraki hardware including Access Points, Switches, Firewalls, and Cameras.
• Troubleshoot LAN, VLAN, and WLAN issues.
• Provide Tier 2 support to existing help desk staff.

System Administration

• Perform OS updates, patching, and endpoint security tasks through Microsoft Intune/Defender.
• Work in coordination with our MSSP to ensure a safe and secure environment.
• 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.

Qualifications: Required Skills & Experience

• Mandatory: At least 5 years' experience with ticketing systems
• 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.
• Mandatory: Hands-on experience with Microsoft Entra ID, Intune/Autopilot, and Exchange Online.
• Mandatory: Proficiency with Windows 11 and macOS troubleshooting.
• Working knowledge of networking fundamentals (DNS, DHCP, TCP/IP, VPN, VLAN, WLAN).
• Ability to be on call for minimal after-hours support, weekly on call rotation with another helpdesk professional - typically a few calls per month.
• Excellent communication, customer service, and problem-solving skills.
• Experience with ITIL-aligned processes and service management best practices.

Preferred Qualifications

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

Compensation & Benefits

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.