Technology Trainer and Service Desk Manager
Legal Aid Chicago encourages applicants with relevant volunteer and work experience, who have experiences with our client communities or individuals who identify as a person of color, LGBTQIA+, immigrant, or otherwise having backgrounds and experiences that are underrepresented in the legal profession to apply.

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.


The Technology Trainer and Service Desk Manager is responsible for organization-wide technology training and for the day-to-day operation of Legal Aid Chicago’s Information Technology Service Desk to ensure that our technology meets the needs of our staff. The position reports to the Director of IT and supervises the Service Desk Analysts.

The Technology Trainer and Service Desk Manager develops and presents regular technology training and coordinates the efficient and effective information technology support operations for Legal Aid Chicago and Legal Action Chicago. This position makes regular presentations and creates user-friendly documentation; plans, assigns, and directs work; documents and gains approval for all service desk support procedures and system documentation; and assists team members in answering calls, addressing service or escalation issues, and applies independent decision making to resolve and/or escalate problems as necessary. This position will work with the Director of IT to provide the technology education to the organization including, but not limited to, writing documentation, producing instructional videos, and leading in-person and remote training sessions. This position develops regular reports on service desk contacts, ensures that service levels are met, identifies trends and makes recommendations for service improvements, including technology education for all staff, and provides budgetary recommendations to management for service growth and/or improvement.

Responsibilities without limitation:

Technology Education / Training

  • Create, conduct, and review technical training programs according to organizational requirements
  • Conduct new employee IT onboarding
  • Work with departments to understand training needs, and identify educational sessions, documentation, and other resources to assist staff
  • Assist with production of instructional videos, FAQs, How-To’s, end user guides, and documentation, as determined by the Director of IT
  • Assist with communications about technology education resources to staff, as determined by the Director of IT
  • Identify additional educational session needs by surveying internal departments, reviewing support tickets, etc., and propose solutions

Manage IT Service Desk

  • Supervise the Service Desk Analysts, both to directly support end users and to assist with IT department directives
  • Directly supervise, recruit, train, and support Service Desk staff and evaluate their performance
  • Follow up with customers to identify areas of improvement
  • Develop an effective and workable framework for managing and improving IT support. Identify situations that may require additional support or escalation
  • Ensure service level agreements (SLAs) and KPIs/performance metrics for the service desk and system/network administration teams are achieved
  • Review, develop, and implement IT guidelines and devise new organizational systems as needed
  • Develop guides such as FAQs, How-To’s, or employee training documentation for IT staff

Resolve Service Desk Escalations and After-Hours Support

  • Assist the IT staff with providing service desk functions, e.g. answer staff questions and solve complex computer problems
  • Act as part of the escalation team and facilitator for severe, critical and unique issue
  • Provide after-hours support when necessary


Salary and Benefits:

The Technology Trainer and Service Desk Manager position begins at $70,000 and increases with experience.

Legal Aid Chicago offers a comprehensive benefits package, including:

  • Medical, dental, and vision insurance, effective the first day of employment
  • Time Off: 21 vacation days and 18 sick days accrued within the first year of employment
  • 14 paid holidays, including one floating holiday
  • Six weeks of Paid Parental Leave at 100% of the salary after six months of employment
  • 401(a) retirement plan with an employer contribution after 3 months of employment
  • $100,000 Basic Life and Accidental Death & Dismemberment insurance, at no cost
  • Access to Employee Assistance Program resources, at no cost
  • Monthly internet reimbursement
  • Legal Aid Chicago is a 501(c)(3) non-profit and is an eligible employer for the federal public service loan forgiveness program


The ideal candidate will possess:

  • Experience in delivering effective training sessions to individuals or groups, whether in a classroom setting, online, or through workshops
  • Experience in creating training materials, lesson plans, and course content
  • Exceptional organizational skill with strong attention to detail
  • Excellent written and verbal communications skills and very good listening skills
  • Experience managing a service desk support team
  • Experience in customer-service with a problem-solving attitude
  • Ability to respond to service desk escalations in a professional and courteous manner
  • Solid technical background with an ability to give instructions to a non-technical audience
  • Ability to utilize effective leadership skills in daily interactions with their team members
  • HDI / ITIL 4 Certifications preferred
  • Appreciation of the importance of civil legal aid and the civil justice system, commitment to Legal Aid Chicago’s mission of equal justice for low-income people
  • Education: Bachelor's Degree preferred


Legal Aid Chicago offers a hybrid work environment. Our offices, located in downtown Chicago at 120 S. LaSalle Street, is ADA accessible and has convenient access to public transportation and local expressways.


To Apply: Submit a cover letter, resume, writing sample, and the contact information of two primary professional references and one alternative professional reference. 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, or any other protected status. 

If an accommodation is needed to complete this application, contact Human Resources at