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The Commonwealth of Massachusetts

Director of Workforce Development

Dedham, MA

Job Description

The Director of Workforce Development position works to expose male incarcerated adults enrolled in the School of Reentry at Boston Pre-Release Center to learning processes and educational experiences that will give the skill set and tools to find sustainable employment and/or continued education in order to achieve personal success and productivity. The School of Reentry is committed to and expects the Director of Workforce Development to work to develop working relationships with industry employers and educators geared toward creating opportunities for School of Reentry graduates. Will be responsible for running multiple groups per week in addition to one-on-one career exploration and workforce development planning.

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Duties and Responsibilities (these duties are a general summary and not all-inclusive)

  • Provide individual and group career workforce development planning to assist individuals in gaining insight into their challenges and to develop plans for reentry success.
  • Assist the Executive Director with grant development and research; including presentations to potential funders.
  • Work with the Director of Reentry to provide case management, support and referral services before and upon release by performing advocacy and outreach.
  • Assist the Executive Director with grant development and research; including presentations to potential funders
  • Collaborate with School of Reentry staff, Department of Correction (DOC), and Interperimeter Security Team (IPS) and other departments as required.
  • Develop and maintain relationships with program partners to deliver services and coordinate career plans.
  • Prepare and maintain student records, narrative reports, statistical reports, and other records to facilitate exchange of information.


Created in 2016 by the Executive Office of Public Safety and Security, the School of Reentry (SOR) is a 12-18 month residential school providing minimum security inmates an opportunity to maximize the end of their incarceration time immersed in education, personal, career and technical education training. The mission of the school is to develop a growth mindset within.

Preferred Qualifications

  • Highly organized person with excellent oral and written communication skills with attention to detail.
  • Ability to manage multiple projects across several agencies in a fast pace moving environment.
  • Knowledge of substance use disorder, Motivational Interviewing Techniques, and Reentry Planning.
  • Manage and lead operational plan.

Required Qualifications

  • Lived carceral experience in any state can apply, experience in Massachusetts preferred. Cannot currently be on any form of supervision. Must be at least 5 years from release.
  • In depth understanding of reentry programming and the needs of returning citizens.
  • Experience with grant writing and research.
  • Understanding of and/or personal experience with reentry needs, substance use disorder, homelessness, unemployment, and self-motivation.
  • Experience with data tracking and reporting.
  • Ability to develop recruitment and promotional materials through imaging, video, and audio recordings.



Applicants must have at least (A) five (5) years of full-time or, equivalent part-time, professional, administrative, supervisory, or managerial experience in business administration, business management, public administration, public management, clinical administration or clinical management of which (B) at least one (1) year must have been in a project management, supervisory or managerial capacity or (C) any equivalent combination of the required experience and substitutions below.


I. A certificate in a relevant or related field may be substituted for one (1) year of the required (A) experience.

II. A Bachelor's degree in a related field may be substituted for two (2) years of the required (A) experience.

III. A Graduate degree in a related field may be substituted for three (3) years of the required (A) experience.

IV. A Doctorate degree in a related field may be substituted for four (4) years of the required (A) experience.

Comprehensive Benefits

When you embark on a career with the Commonwealth, you are offered an outstanding suite of employee benefits that add to the overall value of your compensation package. We take pride in providing a work experience that supports you, your loved ones, and your future.

Want the specifics? Explore our Employee Benefits and Rewards!

An Equal Opportunity / Affirmative Action Employer. Females, minorities, veterans, and persons with disabilities are strongly encouraged to apply.

The Commonwealth is an Equal Opportunity Employer and does not discriminate on the basis of race, religion, color, sex, gender identity or expression, sexual orientation, age, disability, national origin, veteran status, or any other basis covered by appropriate law. Research suggests that qualified women, Black, Indigenous, and Persons of Color (BIPOC) may self-select out of opportunities if they don't meet 100% of the job requirements. We encourage individuals who believe they have the skills necessary to thrive to apply for this role.

Client-provided location(s): Roslindale, Boston, MA, USA
Job ID: Commonwealth_of_Massachusetts-240004CB
Employment Type: Full Time

Perks and Benefits

  • Health and Wellness

    • Health Insurance
    • Health Reimbursement Account
    • Dental Insurance
    • Vision Insurance
    • Life Insurance
    • Short-Term Disability
    • Long-Term Disability
    • FSA
    • HSA
    • Mental Health Benefits
  • Parental Benefits

    • Adoption Assistance Program
    • Family Support Resources
  • Work Flexibility

    • Flexible Work Hours
    • Hybrid Work Opportunities
  • Office Life and Perks

    • Commuter Benefits Program
  • Vacation and Time Off

    • Paid Vacation
    • Paid Holidays
    • Personal/Sick Days
    • Volunteer Time Off
  • Financial and Retirement

    • Pension
    • Financial Counseling
  • Professional Development

    • Promote From Within
    • Mentor Program
    • Access to Online Courses
    • Lunch and Learns
    • Internship Program
    • Leadership Training Program
    • Associate or Rotational Training Program
  • Diversity and Inclusion

    • Diversity, Equity, and Inclusion Program