Director Workforce Development Jobs in Chicago, IL

Job Title: EMPLOYMENT SPECIALIST

Department: Workforce Development

Reports To: Director of Workforce & Job Development

Employment Status: Full-Time

FLSA Status: Non-Exempt

Funding Source: Grant-Funded Position

About Westside Health Authority (WHA)

Westside Health Authority is a nonprofit community development organization dedicated to improving the health and well-being of residents in Chicago’s West Side communities, including Austin, Garfield Park, and Lawndale. WHA empowers individuals and strengthens neighborhoods through employment opportunities, reentry support, youth mentorship, property development, and community engagement.

POSITION SUMMARY

The Employment Specialist is responsible for providing workforce development, employment preparation, job placement support, career coaching, and retention services to program participants. This position works directly with individuals experiencing barriers to employment, including justice-involved individuals, returning citizens, individuals impacted by community violence, and residents seeking economic stability and career advancement opportunities.

The Employment Specialist assists participants with developing workforce readiness skills, identifying employment opportunities, preparing for employment, and maintaining successful employment outcomes. The position provides participant-centered support designed to promote self-sufficiency, workforce engagement, and long-term career success.

The Employment Specialist works closely with workforce development staff, community partners, employers, and other Westside Health Authority departments to ensure participants receive comprehensive workforce services and support.

This position is subject to continued funding availability, program performance requirements, and organizational needs.

ESSENTIAL DUTIES AND RESPONSIBILITIES

Employment Services & Career Coaching

• Conduct participant employment and workforce readiness assessments to identify employment goals, strengths, barriers, and service needs.

• Assist participants in developing individualized employment plans and career goals.

• Provide one-on-one employment coaching and workforce guidance throughout program participation.

• Assist participants with job searches, employment applications, resume preparation, interview preparation, and professional development activities.

• Share employment opportunities, hiring events, training opportunities, and workforce resources with participants.

• Assist participants in exploring career pathways, vocational training opportunities, certifications, and employment options aligned with their interests and goals.

• Support participant employment placement efforts and employment readiness activities.

Workforce Readiness & Participant Engagement

• Facilitate workforce readiness, job readiness, and employment preparation workshops as assigned.

• Assist participants with developing workplace professionalism, communication skills, conflict resolution skills, and workplace expectations.

• Support participants with digital literacy skills, online job applications, virtual interviews, and workforce technology platforms.

• Assist participants with Illinois WorkNet registration, LinkedIn profile development, and other workforce development resources.

• Maintain regular communication with assigned participants to encourage engagement, attendance, and successful completion of workforce activities.

• Encourage participant accountability, motivation, and commitment to employment goals.

Employment Retention Services

• Conduct employment retention follow-up activities in accordance with program and funding requirements.

• Maintain communication with employed participants to support job retention and workplace success.

• Track participant employment status, wages, retention milestones, credential attainment, and employment outcomes.

• Assist participants in addressing employment-related challenges through referrals and supportive service resources.

• Document employment placements, retention outcomes, and participant progress.

Case Documentation & Compliance

• Maintain accurate, complete, and timely participant records in Apricot, CiviCore, and other required data management systems.

• Complete case notes, participant contacts, assessments, employment verifications, referrals, and service documentation within established timelines.

• Ensure compliance with organizational policies, program requirements, grant guidelines, and documentation standards.

• Collect and maintain participant information necessary for performance tracking, reporting, audits, and monitoring activities.

• Maintain confidentiality of participant information and records.

Collaboration & Program Support

• Work collaboratively with the Director of Workforce & Job Development, Program Manager, Case Manager/Intake Specialist, and workforce development staff.

• Participate in staff meetings, supervision sessions, case reviews, trainings, and organizational meetings.

• Support workforce development activities, participant recruitment efforts, outreach initiatives, and special projects as assigned.

• Assist with participant enrollment, orientation, and engagement activities.

• Collaborate with internal departments and community partners to support participant success.

Community Engagement & Representation

• Represent Westside Health Authority in a professional manner at job fairs, hiring events, community meetings, workforce development activities, and public events.

• Participate in community outreach activities designed to recruit participants and promote workforce development services.

• Build positive working relationships with participants, employers, community partners, and stakeholders.

• Attend occasional evening and weekend activities as required.

QUALIFICATIONS

Education & Experience

• High School Diploma or GED required; Associate Degree in Human Services, Workforce Development, Business Administration, Social Work, Education, or a related field preferred.

• Minimum of two (2) years of experience in workforce development, employment services, career coaching, case management, reentry services, community engagement, violence prevention, or a related field preferred.

• Experience working with justice-impacted individuals, returning citizens, Community Violence Intervention (CVI) participants, and individuals facing barriers to employment preferred.

• Demonstrated ability to establish rapport, build trust, and maintain professional relationships with diverse populations.

• Valid Illinois Driver's License and reliable transportation preferred.

KNOWLEDGE, SKILLS, AND ABILITIES

• Knowledge of workforce development principles, employment preparation, workforce readiness, and job placement practices.

• Strong verbal, written, and interpersonal communication skills.

• Ability to work effectively with diverse populations and individuals experiencing barriers to employment.

• Strong organizational, time management, and problem-solving skills.

• Ability to maintain accurate records and documentation.

• Proficiency in Microsoft Office Suite, including Word, Excel, Outlook, and Teams.

• Experience utilizing Apricot, CiviCore, or similar case management systems preferred.

• Ability to maintain confidentiality and handle sensitive participant information appropriately.

• Commitment to professionalism, accountability, cultural responsiveness, and participant-centered service delivery.

WORK ENVIRONMENT

This position operates in a professional office, classroom, community, and field-based environment. Duties require regular interaction with participants, employers, community partners, and organizational staff. Local travel throughout Chicago and surrounding communities may be required. Evening and weekend hours may be necessary to support workforce development activities, outreach events, and community engagement efforts.

PERFORMANCE EXPECTATIONS

• Maintain accurate and timely participant documentation and case records.

• Meet employment placement, retention, engagement, and performance goals established by funding sources and organizational leadership.

• Demonstrate professionalism, reliability, accountability, and effective communication.

• Support participant engagement and successful completion of workforce development services.

• Adhere to organizational policies, grant requirements, and program standards.

• Support the mission, vision, values, and goals of Westside Health Authority.

Compensation & Benefits

• Salary: Commensurate with experience
• Benefits: Comprehensive benefits package including health, dental, vision, life insurance, paid time off, holidays, and retirement plan options.
• Schedule: Full-time, Monday–Friday, occasional evenings/weekends for events or community meetings.

DISCLAIMER: The duties and responsibilities described are not intended to be a comprehensive list of all activities, duties, or responsibilities required of the employee. Duties may change at any time with or without notice to meet organizational, operational, programmatic, or funding requirements.

Westside Health Authority is an Equal Opportunity Employer committed to providing equal employment opportunities for all qualified applicants and employees.