System Administrator
Job Type

For over 50 years, Legal Aid Chicago has provided free civil legal assistance to people living in poverty in metropolitan Chicago. Each year our attorneys, volunteers, and staff help resolve civil legal problems, including domestic violence, consumer fraud, and unfair evictions. Legal Aid Chicago was founded on the philosophy that all individuals are entitled to quality civil legal representation, regardless of their income. We work to ensure that poverty is not an impediment to justice by dismantling the legal barriers that perpetuate inequality. Legal Aid Chicago staff live our mission through our core values of equity, excellence, inclusion, kindness, and respect.

Position: The System Administrator works closely with the IT Operations Manager and Director of Information Technology and is responsible for system administration of the IT servers and systems, providing input and completing tasks on major technology projects, and providing technical support to staff. This is a full-time position that reports to the IT Operations Manager.

This position is hybrid and weekly in-office attendance will be required.


  • Providing technical assistance with empathy and willingness to engage and support for incoming requests and issues related to end-user computer systems, software, and hardware.
  • Desktop administration and maintenance for Microsoft Windows 10, iOS, Android phones & tablets
  • Support laptops, tablets, printers, scanners, faxing, phones, email, websites, and applications.
  • Prioritize and follow up on tickets until resolved.
  • Assist with help desk functions including the assessment of and resolution to escalated requests from the Service Desk Analysists/Specialists and Systems Administrators. 
  • Provision new equipment with attention to detail and quality.
  • Assist in developing and documenting efficiencies for service desk & network operations processes, onboarding & offboarding.
  • System administration of Microsoft services including Active Directory, Azure and Office 365.
  • Phone system maintenance and administration (Moves, Adds, and Changes, etc.) for Cisco phone system.
  • Help desk activities for internal and remote employees to benefit immediate productivity restoration.
  • Technology inventory control and tracking.
  • Ability to train staff on supported applications both remotely and potentially in-person.
  • Strong skills with developing and maintaining  documentation for systems and processes.
  • Demonstrate initiative in problem solving areas, skill  improvement by taking advantage of training classes, and seeking training from senior staff.
  • May require after-hours support/on-call rotations to respond to outages and priority incidents.
  • Other duties as assigned.

Salary: Starting at $55,000, commensurate with experience. Legal Aid Chicago offers a comprehensive benefits package, including low cost health plans, employer-provided group life and long-term disability insurance, fitness center access, generous vacation and sick time, and more. 



  • Associates degree in Computer Science or equivalent OR 4+ years help desk/systems administration experience.
  • Knowledge of Microsoft 365/Office 365 administration.
  • Excellent organizational and time management skills with strong attention to detail.
  • Proven record of follow-through on assigned tasks.
  • Excellent written and verbal communication including communication with staff and developing and maintaining documentation for systems and processes.


  • Experience with PowerShell scripting.
  • Experience administrating, maintaining, and monitoring active directory, group policy, DHCP, and DNS in an enterprise environment
  • Knowledge and understanding of SCCM clients (hardware/software) including but not limited to installing, configuring, maintaining, optimizing, and supporting clients.
  • Experience with telephone systems (e.g. Cisco UCCX/CUCM).
  • ITIL 4 certification.
  • Previous law firm or non-profit experience.

Physical Demands: Must possess mobility to work in a standard office setting and use standard office equipment, servers, and network equipment. Must be able to operate a motor vehicle and visit various sites; vision to read printed materials and a computer screen and ability to distinguish colors; and hearing and speech to communicate in person, before groups, and over the telephone. Finger dexterity is needed to access, enter, and retrieve data using a computer keyboard, typewriter keyboard, or calculator and to operate standard office equipment. This position will require the ability to bend, stoop, kneel, reach, lift, push and pull drawers open and closed to retrieve and file information. An employee in this position  must be able to lift, carry, push, and pull materials and objects weighing up to 40 pounds with the use of proper equipment. 

Cover letter, resume, and the contact information of two professional references are required to apply. Applications will be reviewed on a rolling basis, and the position will remain open until filled.

Legal Aid Chicago is firmly committed to creating a diverse workplace and is proud to provide equal employment opportunities to all applicants and therefore does not discriminate on the basis of creed, color, national origin, sex, gender identity, sexual orientation, age religion, marital or parental status, alienage, disability, political affiliation or belief, military or military discharge status, or ex-offender status. Applicants who have experiences with our client communities are encouraged to apply.