System Administrator

inMy Jet; Wheeling, Northern (IL, KY); Hybrid; USD 85,000 - 110,000; Full time

Benefits offered by this job

Health insurance

401(k) retirement plan with company-m

Paid time off (PTO)

Tuition reimbursement

Job summary

George J. Priester Aviation is seeking a System Administrator in Wheeling, IL to manage a 100% cloud environment. You will handle Entra ID, Intune/Autopilot, Exchange Online and Defender, with Meraki networking and Tier 2 helpdesk support. Remote and onsite support are required.

The role demands strong documentation, customer service, and the ability to work in a fast-paced aviation environment under SLAs.

Qualifications

• 5+ years’ experience with ticketing systems.
• 3+ years’ experience with MDM for iPads (MaaS360 and/or Jamf).
• Hands-on with Microsoft Entra ID, Intune/Autopilot, and Exchange Online.
• Proficiency with Windows 11 and macOS troubleshooting.

Responsibilities

• Triage, prioritize, and resolve incidents and service requests within SLA.
• Provide end-user support for Windows, macOS, and iPad devices.
• Manage identity/access through Microsoft Entra ID and MFA/SSO.
• Deploy and manage devices via Intune/Autopilot; configure security baselines.
• Support Meraki network gear and provide Tier 2 helpdesk assistance.
• Create and maintain technical documentation and knowledge base articles.

Skills

Ticketing systems (Freshservice)

MDM for iPads (MaaS360/Jamf)

Microsoft Entra ID/Intune/Autopilot

Exchange Online/Defender

Windows 11 troubleshooting

macOS troubleshooting

On-call support

ITIL/Service management

Education

CompTIA A+/Network+ or Microsoft Cloud certifications

Tools

Freshservice

Microsoft Entra ID

Intune/Autopilot

Meraki

Jamf

Job description

# System AdministratorPriester AviationWHEELING, IL 6009011 days agoJob descriptionDescriptionJob Title: System AdministratorLocation: Wheeling, IL (Chicagoland area)About George J. Priester AviationGeorge 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.OverviewThe 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 ResponsibilitiesIT 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.QualificationsRequired 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 & BenefitsGeorge 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 plansFinancial & 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 optionsTime Off & Work-Life Balance• Paid company holidays• Unlimited Paid Time Off (PTO), subject to scheduling guidelines• Sick leave in accordance with company policyAdditional Benefits• Tuition reimbursement program• Company-paid legal services and identity theft protection• Company-paid pet insurance for dogs or cats• Employee assistance and support resourcesBenefits eligibility and offerings may vary based on role, employment type, and client program.Work EnvironmentThis 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 EmployerGeorge 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.