Career Advisor - Reentry Community

About WSM

Work Source Montgomery, Inc. (WSM) is a nonprofit organization and fiduciary agent for Workforce Innovation Opportunity Act funding in Montgomery County. The non‑profit organization operates the American Job Centers in Wheaton and Germantown and provides employment services to county residents who are unemployed or underemployed. Additionally, WSM engages employers in various industries throughout the county to ensure that their workforce needs are being met.

The Reentry Career Advisor plays a critical role in supporting justice‑impacted individuals as they prepare for employment, training, and successful reintegration into the community. This position provides intensive case management, individualized career coaching, and employment readiness services specifically tailored to individuals with justice system involvement. The Reentry Career Advisor must have a strong understanding of WIOA guidelines, reporting requirements, and participant eligibility pathways.

The ideal candidate is someone who demonstrates compassion, professionalism, and a genuine commitment to supporting individuals facing significant barriers to employment. This role requires strong coordination with internal WSM teams, correctional partners, community‑based organizations, and workforce training providers to ensure that participants receive comprehensive support throughout pre‑release and post‑release phases.

• Provide trauma‑informed, individualized career advising to justice‑impacted clients, including assessments, interest inventories, barrier analysis, and career pathway exploration.
• Develop and manage Individual Employment Plans (IEPs).
• Maintain an active caseload, using case management best practices to monitor progress, provide support, and ensure timely completion of milestones.
• Guide participants through employment readiness activities including résumé development, interview preparation, job applications, and labor market research.
• Conduct frequent check‑ins with clients (in‑person, virtual, or phone) to provide coaching, motivation, and support.
• Hold bi‑weekly meetings inside Montgomery County Correctional Facility to meet with clients pre‑release.
• Collaborate with reentry partners, community organizations, and justice system staff to ensure continuity of services and resource coordination.
• Assist participants with connecting to wraparound services such as transportation, training opportunities, financial literacy, housing resources, and behavioral health supports.
• Demonstrate a strong understanding of the reentry landscape, including barriers faced by individuals with justice involvement and best practices for successful reintegration.
• Ensure all activities, case notes, and outcomes are accurately documented in the Maryland Workforce Exchange (MWE) and internal WSM databases.
• Maintain documentation and files that are fully compliant with WIOA regulations, including eligibility verification, services provided, progress tracking, and employment outcomes.
• Promptly close cases and complete follow‑up reporting within established timelines.
• Work closely with Talent Placement to secure work experience and placement opportunities.
• Participate in team meetings, cross‑functional projects, and events that advance reentry programming and workforce initiatives.
• Attend required trainings, workshops, and events as needed.
• Perform other duties as assigned.

• Knowledge of WIOA, workforce development programs, and case management practices.
• Ability to work effectively with diverse populations, especially individuals with significant employment barriers or justice involvement.
• Strong verbal and written communication skills, including presentations and group facilitation.
• Proficiency with Microsoft Office Suite and comfort with learning workforce data systems (e.g., MWE).
• Ability to build trusting relationships, demonstrate cultural humility, and maintain professional boundaries.
• Strong organizational skills, time management, and the ability to manage multiple priorities.
• Commitment to social justice, reentry support, and reducing employment inequities for…