System Admin
Chicago, IL US
Posted ago

This is a Work-From-Home position.

The Systems Administrator is responsible for providing a highly reliable infrastructure for all end-user and computing environments and ensuring all PC, Network, Cloud, and Server related solutions are sustained with visible and defined metrics. Responsible for maintaining a solution roadmap related to PC and Server enterprise environment. Additional responsibilities include timely remediation of system alerts and outages. 

The Systems Administrator is an escalation partner for service desk-related support activities and facilitates programmatic software deployments and updates. Additional responsibilities will be assigned as business and technology needs evolve.  


Overall Microsoft network support and administration

  • Azure Active Directory Management (user and policy definitions and implementation)
  • Manage Policies applied to workstations, laptops, and servers via Intune

Plan, coordinate, and execute all PC and server-related updates and changes

  • Installation and configuration of cloud or on-premise (hosting provider) Microsoft servers
  • Oversee PC/laptop system image standards
  • Management and configuration of remote management tools
  • Management of software deployments and patches through the use of enterprise software tools
  • Managed server and M365 backup/recovery solutions and services
  • Manage printer definitions and user access
  • Fulfill and apply the organization’s system management policies for the PC environment

Direct day-to-day management and coordination with mission-critical, 3rd party cloud/hosted solution providers

  • Provide assistance and support for the Teams telecom solution
  • Fulfill the role of the main technical point of contact for day-to-day operations with cloud data center and M365 vendors
  • Liaise with RealPage, third-party MSPs, and similar support vendors


  • Create and maintain technology infrastructure documentation, workflows, changelogs, processes, and procedures
  • Provide Technology Services department management with periodic resource utilization reports, incident reporting, and summary of recent activities
  • Recommend and define software and hardware standards
  • Facilitate the technology aspects of the staff onboarding and off-boarding workflows
  • Recommendation for and procurement of PC and server-related hardware/software
  • Project management of infrastructure upgrades and changes
  • Assist with business case development for new and related projects and investments
  • Sustain ongoing PC and server management recommendations and plans to evolve services with the needs and direction of the company
  • Test and improve the Technology Services department’s ability to back up and recover systems during a disaster.
  • Other duties as assigned by the Technology Services Department leadership


  • Computer Science or related certificates preferred
  • Microsoft MCP or role-based certificates is desired
  • 6-8 years of Incident Management experience
  • 6-8 years previous IT Service Desk and/or Call Center experience required
  • Excellent communication, time management, decision making, presentation, and organizational skills
  • Strong knowledge of Real Estate, Leasing, and Finance - as it relates to the services and products offered by Mayroad is desired
  • Must be flexible / Available to work staggered shifts and weekend support as requested
  • Must be able to travel out of state 
  • Strong Microsoft operating system and enterprise network experience (MCSE preferred)
  • Strong ability to troubleshoot and resolve issues and problems
  • Experience as a System Administrator in Real Page or similar property management software
  • 5 yrs Microsoft Azure Active Directory, Group Policy, WSUS, SCCM, experience required
  • Expert in Windows 10 and/or Server administration
  • Expert in M365 administration
  • 5 yrs RealPage troubleshooting and configuration
  • SharePoint admin experience (security, site creation, customization)
  • Strong familiarity with ITSM systems
  • Microsoft Teams (administration/troubleshooting)
  • Basic understanding of layer 1-3 OSI model
  • Proficiency with Incident Response, handling spam, malware, and email security applications
  • A Plus: Working knowledge of networking: Strong TCP/IP awareness, sub-netting, VLANS, SD-WAN

About Mayroad

Mayroad, an asset management company, has an established leadership heritage of over 20 years of experience operating mission-critical assets that contribute to better outcomes for the communities in which they serve. 

Mayroad’s mission is simple: create and foster long-term sustainable partnerships while ensuring the highest level of customer service and social responsibility are delivered to those whose lives we impact every day. 

Our current portfolio features over 4,000 homes across six Air Force installations.

Mayroad provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, protected veteran status, or any other characteristic protected by federal, state, or local laws.

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