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Employment Resource Specialist

Req ID: 7960
Location: Chicago - Loop
# of Openings: 1
FT/PT: Full time
Employment Type: Regular
Salary Schedule:
Job Notes:


Heartland Alliance coordinates READI (Rapid Employment and Development Initiative) Chicago, a network of community-based organizations on Chicago’s West and South Side that engage men at the highest risk of becoming victims or perpetrators of gun violence in a 12-month program that provides employment support, cognitive behavior interventions (CBI), case management, and coaching. The goals of READI Chicago are to: decrease shootings and homicides among those at the highest risk of gun violence; create new opportunities for those same individuals to change their life trajectory and decrease their involvement with the criminal justice system; and help build infrastructure at the community level to promote long-term safety and opportunity in Chicago’s most impoverished communities. Heartland Alliance is also partnering with the Illinois Department of Corrections (IDOC) to deliver elements of READI programming to people who are close to leaving IDOC facilities (prisons) and returning to Chicago, and who are at high risk for gun violence involvement upon release. The project with IDOC is known as “READI for Reentry” (R4R).

Reporting to READI for Reentry’s Program Manager, the Employment Resource Specialist is responsible for delivering employment services specifically to the R4R participants who have been released from prison to Chicago after completing programming in prison. Specifically, this position is responsible for providing individual job coaching to participants though a trauma informed and restorative justice lens; and cultivating and liaising with employer, education, and training partners, and assisting participants in preparing for, applying to, and retaining placements with them. The Employment Resource Specialist is expected to adhere to principles of trauma-informed care, harm-reduction, and strength-based, cultural competency, and restorative justice. The Employment Resource Specialist should be an excellent problem-solver, organized, have great communication skills in both writing and speaking, be energetic and flexible, collaborative, and proactive team members who positively and productively support high-risk participants. The Employment Resource Specialist should have experience in case management and workforce development, as well as working with very high-risk adults and young adults.

Essential Duties and Responsibilities:

Case Management and Career Coaching

  • With the Chicago-based Reentry Specialist, share a caseload of up to 40 READI for Reentry participants.
  • Conduct weekly one-on-one career coaching sessions with participants.
  • Update case notes to document outcomes of career coaching process and next steps.
  • Collaborate with prison-based R4R staff, and participate in participant case staffings
  • In-state travel (to prisons) to meet with prison-based R4R staff and participants to discuss their job readiness and employer requirements every two-to-three months.
  • Guide participant through WIOA grant process to completion and submission.
  • Review and update needs assessment and career assessment (for participant career interests and aptitudes) to match participants with employment opportunities, and appropriate training and education
  • In collaboration with participants, use assessment results to develop Individual Action Plans (IAP) to achieve career and education goals; continually reassesses goals and progress toward goals with participant in weekly sessions
  • Provide job search and application assistance and support development of job search skills
  • Perform mock interviews with and review resumes of participants
  • Refer participants to education, training, and job interviews in alignment with IAP, and assist participants in applying.
  • Support job retention efforts through participant follow-up contacts, check-ins with employers when appropriate
  • Match participants with appropriate self-paced virtual learning modules based on their needs and career interests. Discuss completed modules with participants during coaching sessions.
  • Develop comprehensive services and resources to assist participants with their career and academic planning towards employment goals.
  • Interview, advise, and guide participants to ascertain employability
  • Interpret and explain any employer regulations, rules, policies, and procedures to clients, such as drug screenings or background checks.
  • Collaborate remotely with prison-based Reentry Specialist to review pre-release participants’ career goals and skills and recommend virtual modules and steps participant can take to become job-ready prior to release.
  • Offer job readiness trainings to participants at prisons throughout the state who have an interest in working in a non-profit organization upon release.

Employer Relations

  • Maintain an awareness of local job market and opportunities to assist in providing career guidance to clients; may arrange for employment interviews, attend job fairs, conduct special workshops, presentations, or perform other training and outreach activities.
  • Cultivate relationships with workforce development entities, local economic councils, area and regional employers, training programs, and educational programs.
  • Develop and implement successful marketing strategies to improve the receptivity of employers, businesses, and vocational training facilities for hiring, promoting and/or training program participants.
  • Identify both entry-level and career track positions feasible and attractive to program participants based on their assessments and Individualized Action Plan.
  • Develop and maintain an information bank regarding employment, education (including GED), and vocational training opportunities.
  • Collaborate with READI Chicago and other Heartland staff to adopt and share best practices and resources for workforce development.
  • Track job/education/training placements in a data collection system used to determine job retention at quarterly intervals.


• Participate in professional development trainings including but not limited to trainings focused on principles of trauma-informed care, cognitive-behavioral interventions, motivational interviewing, conflict de-escalation, harm reduction, restorative justice, and other relevant concepts, and apply that knowledge daily

• Become trained in cognitive-behavioral interventions; use CBI language in daily work activities.

• Participate in organizational task groups, serves on committees, and collaborate with service provider networks and policy development groups.

• Complete and submit all required paperwork, data entry, and reporting within 24 hours of service provision 

• Exhibit the highest level of confidentiality and professionalism at all times

• Comply with all IDOC requirements, policies, rules and regulations during performance of services for the Program and at all times while in IDOC facilities

• Other duties as assigned.


• Education and Experience: Bachelor’s degree and 2-3 years of formal work experience in employment-related social services, case management, and career counseling/coaching, preferably with justice-involved individuals, opportunity youth, or similarly at-risk or marginalized populations; OR, an equivalent combination of education and relevant work experience required. Must possess a high school diploma or GED.

• Demonstrated experience utilizing strength-based methods of assessment and working with populations facing multiple barriers to obtain employment, required. 

• Demonstrated experience performing employment services, case management, or career counseling/coaching in a social service setting, preferably with (formerly) incarcerated individuals, opportunity youth, or similarly at-risk or marginalized populations, required.

• Extensive knowledge of occupations, job skills, and labor market trends, community resources and vocational services that impact participants.

• Knowledge of workforce development and employment services for chronically unemployed individuals or individuals experiencing poverty

• Comfort working with high-risk populations with complex needs

• Excellent written and verbal communications skills; excellent organizational skills

• Skilled in Microsoft Office, including Word, Excel, Outlook, Teams, and PowerPoint; Windows operating systems; Zoom; and other commonly used software. Experience with prison email and virtual visit software such as GTL, a plus.                                                                                                                                

• Basic understanding of cognitive-behavioral interventions, motivational interviewing, and trauma-informed care, preferred

• Commitment to the mission and values of READI Chicago, as demonstrated by a professional approach that is strength-based, trauma-informed, inclusive, and grounded in human rights

• Access to reliable transportation and ability to travel throughout Chicago, surrounding areas, and Danville, IL.

• No current gang affiliations

• Individuals with criminal records and other lived experience are encouraged to apply, however the Employment Specialist must be able to obtain security clearance at IDOC. This means the Employment Specialist cannot have any IDOC infractions (Inmate Disciplinary Reports) for violating security protocol in the past seven years.

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Heartland Alliance requires all employees to be fully vaccinated against COVID-19 unless Heartland has approved a medical or religious accommodation for you consistent with applicable laws and regulations.