Training and Support Specialist

Chicago Cook Workforce Partnership; Chicago (IL); On-site; USD 70,000 - 95,000; Full time

Job summary

Chicago Cook Workforce Partnership is seeking a Training and Technical Assistance Specialist to design and deliver comprehensive training programs across grant-funded initiatives. You will ensure compliance, operational efficiency, and high-quality service delivery throughout the network.

Responsibilities include providing technical assistance to delegate agencies, guiding on mandated service order of operations, and delivering engaging training sessions for large audiences using IWDS 2.0 and

Qualifications

• Excellent written and verbal communication.
• Strong organizational skills and time management.
• Experience in planning, coordinating, and delivering training.

Responsibilities

• Provide training and technical assistance to delegate agencies on programmatic issues.
• Interpret and ensure compliance with WIOA, CEJA, and related policies.
• Design and deliver in-person workshops and large webinars for diverse audiences.

Skills

Verbal communication

Writing/editing

Organizational skills

Microsoft Office

Diversity & equity

Problem solving

Travel flexibility

Education

Bachelor’s degree in human service administration

Tools

MS Office

Job description

Job Summary:

Under the general direction of the Manager of Training and Support, this role provides programmatic technical assistance to agencies within the Chicago Cook Workforce Partnership’s network across a variety of grant-funded programs. This role is responsible for designing and delivering comprehensive training solutions, including in-person workshops and large-group webinars, to ensure compliance, operational efficiency, and high-quality service delivery throughout the network.

Responsibilities:

• Provide comprehensive training and technical assistance to delegate agencies on core programmatic matters, including customer flow reviews and the implementation of specific grant regulations. Interpret and ensure strict adherence to the Workforce Innovation Opportunity Act (WIOA), the Climate & Equitable Jobs Act (CEJA), and other local, state, and federal policies. Guide agencies on mandated order of services, proactive measures for avoiding audit findings, and strategies for ensuring consistent quality in service delivery.
• Facilitate engaging, informative training workshops and webinars focusing on complex program regulations, reporting structures, and operational procedures for large audiences.
• Provide technical instruction, onboarding, and hands-on guidance for essential systems of record, including Illinois Workforce Development System (IWDS 2.0) Illinois workNet Climate & Equitable Jobs Act (CEJA) reporting system
• Monitor and respond efficiently to incoming technical assistance requests originating from the Illinois Workforce Development System (IWDS 2.0).
• Proactively evaluate delegate agency operations to identify localized needs for intervention, troubleshooting procedural problems as they arise.
• Partner closely with Program Relationship Managers to streamline internal coordination, optimize communication, and manage delegate agency performance effectively.
• Monitor network operations to identify systemic issues as well as transferable best practices among delegate agencies to foster continuous improvement.
• Frequently required to stand, walk and sit
• Frequently required to utilize hand and finger dexterity using a keyboard
• Frequently required to talk or hear
• Occasionally required to lift/push/carry items up to 25 pounds
• Assist workforce providers with the practical implementation of key administrative policies and operational procedures.
• Assist the ITA Coordinator with the Eligible Training Providers List (ETPL) review to ensure program alignment and compliance.
• Perform all related duties, special projects, and organizational responsibilities as assigned by management.

Required Skills:

• Excellent verbal communication skills and a proven ability to write, edit, and proofread highly professional documents, policies, and training materials.
• Exceptional organizational and time management skills, featuring a proven ability to prioritize competing tasks, manage multiple projects simultaneously, and meet strict deadlines.
• Demonstrated ability to function effectively, maintain composure, and make sound decisions in a high-paced, dynamic, and at times stressful workspace environment.
• Proficient with Microsoft Office Suite (Word, Excel, PowerPoint, Outlook) or closely related project management and reporting software.
• Ability to demonstrate tact and diplomacy when dealing with employee issues across a wide range of diverse situations.
• Ability to work effectively in a racially diverse environment where advancing racial equity in workforce development, economic development, or human services is a primary focus.
• Considerable knowledge of the Workforce Innovation and Opportunity Act (WIOA) and related compliance entities.
• Ability to solve problems, identify operational errors, irregularities, or illegal acts, and decisively take appropriate corrective action.
• Graduation from an accredited college or university with a bachelor’s degree in human service administration, Social Work, or Social Services preferred; Supplemented by two (2) years of full-time professional paid work experience in program management, auditing or monitoring in the fields of workforce development or other federally/state funded grant programs OR six (6) years of work experience performing these job duties;
• 0-2 years of full-time paid professional work experience providing fiscal or programmatic assistance with programs funded through WIOA is preferred
• Ability to travel throughout the region, state and nationally, if necessary.

Education and Experience:

• Graduation from an accredited college or university with a bachelor’s degree in human service administration, Social Work, or Social Services.
• 0-2 years of full-time paid professional work experience providing fiscal or programmatic assistance with programs funded through WIOA.
• Ability to travel throughout the region, state and nationally, if necessary.

Physical Requirements:

• Frequently required to stand, walk and sit
• Frequently required to utilize hand and finger dexterity using a keyboard
• Frequently required to talk or hear
• Occasionally required to lift/push/carry items up to 25 pounds