Reentry Services Senior Specialist

Job Locations US-MD-Rockville
Category Mission and Partnerships


TITLE: Reentry Services Senior Specialist
RESPONSIBLE TO: Reentry Services Program Director
DIVISION/DEPART: Mission and Partnerships


NOTE: This position is made possible by a grant to Goodwill Industries International (GIl) from the U.S. Department of Labor Employment and Training Administration (USDOLETA). The position's establishment and continuance is dependent upon on-going grant funding.



• Provide technical assistance to local Goodwill® organizations deploying reentry services.
• Ensure fidelity to program model via the Opportunity Accelerator, continuously assess effectiveness, and modify as needed to support success in achieving programmatic and financial outcomes.
• Create, refine and deploy tools and resources to advance the reentry service portfolio.


1. Collaborate with program director to engage subgrantees in peer learning, training and coaching on reentry services, case management, cognitive behavior therapy, accelerated learning models, skills attainment, work-based learning, employment and career advancement services, integration of virtual and in-person resources, and effective grant management practices.
2. Ensure fidelity to the reentry project model(s) via the Opportunity Accelerator, continuously assess effectiveness, and modify approaches as needed to achieve programmatic and financial outcomes.
3. Provide technical assistance to local Goodwill organizations deploying reentry project(s) by equipping, training, supporting and monitoring performance.
4. Create, refine and deploy tools and resources to advance the reentry service portfolio while identifying, documenting and promoting effective practice replication/adaptation. Communicate these via MyGoodwill, consultation, webinar, learning events and, as authorized, sharing with national entities.
5. Co-lead opportunities for interested Goodwill organizations to enhance the model by contributing locally-tested effective and emerging practices.
6. Use data on programmatic performance, grant spending and leveraged resources to design and provide technical assistance to Goodwill reentry project(s) subgrantee teams while equipping subgrantees to use data to self-monitor program performance and budgets; develop projections; make recommendations for needed course corrections; and create reports to inform GIl leadership, subgrantee leaders, and USDOLETA.
7. Conduct virtual program file reviews to validate completeness and accuracy of data being entered into subgrantee participant files and required case management and data reporting systems.
8. Review GII and subgrantee project budgets and spending plans in coordination with the program director and grant accountant.
9. Identify opportunities and risks that can enhance or threaten the success of the Goodwill reentry project(s) and work with GIl team members and subgrantees to proactively deploy timely and effective responses.
10. Co-lead virtual and on-site interventions to help mitigate subgrantee performance challenges.
11. Conduct virtual and on-site subgrantee program monitoring visits using established procedures.
12. Use information from USDOLETA and its representatives and in-depth knowledge of relevant laws, rules, regulations and instructions to guide subgrantees in implementation of the project.
13. Support GII’s participation in a USDOLETA evaluation of reentry services as required.
14. Ensure reentry related content on MyGoodwill is current and relevant.
15. Perform other duties as needed to ensure success of the Goodwill reentry project(s) and Goodwill organizations operating reentry services.

All duties are considered to be essential, unless otherwise indicated.

Internal: Frequent contact and collaboration with GII colleagues.
GII Members: Frequent contact and consultation with local Goodwill leaders.
Outside: Occasional contact with national organizations to leverage resources for GII and local Goodwills.
Government Officials: Occasional contact with USDOLETA or its representatives as needed to communicate program success, seek policy and practice clarifications, and report program progress.


A. Ability to establish trust, build relationships, and demonstrate integrity and credibility with GII colleagues, local Goodwill team members and other stakeholders.
B. Ability to identify, communicate and broker effective programmatic and grant management practices.
C. Demonstrated knowledge of and ability to provide technical assistance, coaching and consultation on reentry services, workforce development practices, business engagement approaches and grant management.
D. Excellent written, electronic and oral communication and presentation skills.
E. Ability to work effectively both independently and collaboratively as part of a team with GII colleagues, local Goodwill team members and representatives of other organizations.
F. Demonstrated effectiveness in producing on-time deliverables with expected quality by managing time and priorities.
G. Ability to travel as required.
H. Effective with an array of computer applications, webinar and intranet mechanisms. Proficiency in web research, Google office suite, Word, PowerPoint, Excel and Outlook required.

Bachelors or Master’s degree in human services, business or other relevant field.

1. Minimum of two years of progressive grant management experience.
2. Experience with reentry services, workforce development practices, learning principles or other relevant experience.
3. Experience working with data management systems and budgets.
4. Experience providing virtual assistance preferred.

Decisions on scheduling tasks, determining priorities, managing time and responding to requests for information. Monitors and assesses risks and opportunities in the operation of a time-limited grant with defined performance objectives. Makes recommendations to management for action.

Regular with latitude given to select appropriate procedures. The work is reviewed primarily for the quality of outcome and secondarily for approaches, procedures and methodologies used to complete the work. Guidance and review may be required on some work problems and projects.

Sedentary, lifting 10 pounds maximum. Walking or standing is required only occasionally. Requires long hours at a computer. Travel required.

Work environment usually hectic with periods of high stress. Will need a positive attitude to meet daily challenges.


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