Demo

Career Coach

OAI Inc.
Chicago, IL Full Time
POSTED ON 3/13/2026
AVAILABLE BEFORE 5/12/2026

OAI JOB OPENING

Position Title: Career Coach

(Full time, non-exempt)

Location: 3901 S. State St. Chicago, IL 60609

Flexible Hybrid: Work from home/Dawson Tech Office/In community

Reports to: Program Manager

Oversees: n/a

Salary: $45-52K per year

How to Apply?

To apply, submit cover letter describing your interest and experience along with your resume to oaihr@oaiinc.org

Who Are We?

As a premier workforce education, training, and development organization, OAI’s mission is pretty simple: to improve lives. We do that through offering training that leads to safe, meaningful employment while helping companies and communities to thrive. Our commitment to Diversity, Racial Equity and Inclusion means you will be joining a very diverse and dynamic team of professionals who are enthusiastically dedicated to our mission. Big thinkers, strategists, problem solvers, caring fun-lovers … OAI is a place that encourages innovative thinking and values flexibility and work-life balance. Our hard-working team is supportive and collaborative and all share a common desire to help our fellow citizens live better, safer lives. We’re a growing non-profit and we’re looking for people to grow with us!

Who Are You?

You’re a mentor, motivator, and collaborator. You enjoy helping others find their true potential through self-discovery and goal setting. You are committed to community growth and being part of that change. If this is you, we need you to join our team!

The Career Coach at our OAI Office at the Dawson Technical Institute of Kennedy King College,primarily works with clients to create and execute career plans. Responsibilities include holding one-on-one coaching sessions, hosting development workshops, cultivating and maintaining training partner relationships, and following up with clients at training sites. The career coach works closely with Employer Relations Specialists for retention activities.

Why OAI?

Remember when we said at the top that we value work-life balance? That’s legit; OAI’s pay and benefits are generous! Benefits include:

· BCBS medical and dental insurance

· VSP vision

· Short- and long-term disability insurance

· Professional development opportunities

· Seven paid holidays plus we are closed between Christmas Eve and New Year’s Day

· Hybrid office setting

· Paid time off

· Weekly mental health time off

· Monthly Internet/phone reimbursement

· 401k Plan with match

· Excellent technology and IT support

· Employee Assistance Network

OAI provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, sexual orientation, gender identity, disability or genetics.

Key areas of responsibility:

Direct Participants Services

  • Provide individualized career coaching, and case management to assess participant motivation, employment readiness, and career interests.

· Provide individual financial counseling/coaching to program participants and complete detailed financial assessments. Develop plans of actions and provide tools, resources, and accountability to the client to help them meet their goals.

  • Develop and document individualized career and retention plans with participants.
  • Work closely with Program Coordinators to establish employment plans and determine program suitability.
  • Support participants through application, interview, and job placement processes.
  • Facilitate job readiness workshops including resume development, labor market research, interviewing skills, and workplace expectations.
  • Maintain consistent communication with participants through meetings, phone calls, and electronic communication to support retention and career advancement.
  • Coordinate youth-centered activities or cohort engagement activities as needed.
  • Facilitate financial capability workshops covering topics such as budgeting, savings, banking products, credit building, and identity protection.
  • Adapt or develop workshop materials to meet the needs of program participants.
  • Connect participants with financial and community resources that support long-term financial health.

Service Coordination

  • Meet regularly with internal Employer Retention Specialist to match participants to employment opportunities
  • Work closely with Financial Coach to connect participants to support services and one-on-one financial coaching
  • Work collaboratively with entire OAI team to provide a high level of service coordination
  • Maintain a network of referral partners to support participant financial and social service needs.

Impact and Data Management

  • Maintain participant records via Salesforce and funder databases including contact information, case notes, career plan progress, job placement, retention, wages and employment activities

· Coordinate and report on participants’ retention activities and other reports per program parameters

· Assist in grant application research and writing, report completion and database updates as needed

Required Qualifications:

· High School Diploma or G.E.D. Certificate required. Four-year college degree in a human services, finance, budgeting, or related field preferred - equivalent work experience will be considered.

· Community outreach, case management, and employer relations experience

· Motivated, self-directed, and conscientious of various roles and responsibilities

· Ability to communicate ideas, advice, feedback and critiques professionally and concisely in individual and group settings

· Ability to recognize weaknesses and develop plans to aid in personal and career growth

· Proficiency in MS Office including Word, Excel, and PowerPoint. Experience with Salesforce data management system or similar client based platform

· Bilingual Spanish-English is a plus

· Must have automotive transportation for reimbursable local job-related travel. Valid driver’s license and auto insurance required

· Flexible hybrid position with in-person client meetings and off-site community and employer meetings

Equal Opportunity:

Diverse candidates are encouraged to apply.

Pay: $45,000.00 - $51,000.00 per year

Benefits:

  • 401(k)
  • 401(k) matching
  • Dental insurance
  • Flexible spending account
  • Health insurance
  • Life insurance
  • Mileage reimbursement
  • Paid time off
  • Parental leave
  • Professional development assistance
  • Vision insurance

Work Location: In person

Salary : $45,000 - $52,000

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