Director of Workforce Development Training

Jubilee Housing•Washington, DC

1d•$100,000 - $112,000•Hybrid

About The Position

The Director of Workforce Development Program leads Jubilee's workforce development programming for returning citizens currently living within Jubilee Housing, with a primary focus on KEB's pre-employment training and the range of skill-building pathways available to residents once they've stabilized. This role has four core areas of responsibility: Delivering internal pre-employment training to residents; Building and maintaining the external employer and partner relationships that make those pathways real; Cultivating and maintaining Jubilee's own practicum sites at Jubilee Farms and Jubilee Kitchen; and Coordinating with the case management team to track and support residents' progress throughout their workforce development journey. Employer relationships are central to this role, not a secondary duty. To execute on the items above, the Director is expected to stay current on workforce needs and hiring demand in the sectors most relevant to Jubilee's residents, and to make sure the pathways offered, whether that's a practicum placement at Jubilee Farms or Jubilee Kitchen, an outside apprenticeship, or a partner credential program, are aligned to local employer needs. This role also offers the opportunity to help build the program it will eventually run. It starts in program design and strategy, working alongside leaders across the organization through design and launch, and transitions into delivery once KEB opens. After launch, the Director will work closely with senior leadership and the case management team to ensure workforce programming stays well-integrated into the broader program arc, and that residents receive consistent support as they move through training, into a skill-building pathway, and toward employment. This is a role for a practitioner looking to grow into management and program design. The person in this seat will be in the room with residents, delivering training, troubleshooting in real time, and building the kind of trust that makes workforce development work for people coming home from incarceration. They will also be Jubilee's face to the employer and training partner community, building and maintaining the relationships that create real opportunities for residents. This position has been designated by the hiring department to require a background check and drug screening as a pre-employment condition.

Requirements

Bachelor's degree required, though demonstrable evidence of equivalent experience will be considered.
3+ years of experience in workforce development, adult education, job training, or a related field.
Demonstrated experience building and maintaining employer relationships, ideally with direct responsibility for aligning training or placement pathways to real hiring demand.
Experience working with people who have been incarcerated, or with other populations facing significant barriers to employment.
Demonstrated ability to design and deliver training curriculum for adult learners, including participants with varied educational backgrounds.
Familiarity with trauma-informed approaches and the ability to work with participants who may be navigating complex challenges alongside their workforce goals.
Strong interpersonal and facilitation skills; comfort in a practitioner role that involves direct engagement with residents.
Experience with data tracking and program reporting.

Nice To Haves

Personal lived experience with the criminal justice system is valued and welcomed.

Responsibilities

Design and deliver a foundational pre-employment curriculum for KEB residents, covering core employability skills including digital literacy, financial literacy, workplace communication, anger management, conflict resolution, professional expectations, and applied problem-solving.
Facilitate training sessions in a trauma-informed, strengths-based manner that meets residents where they are and builds genuine confidence alongside practical skills.
Adapt training content and delivery to meet the diverse needs, learning styles, and prior experiences of participants.
Track resident participation and progress in the pre-employment curriculum and use that data to improve training over time.
Collaborate with the case management team to ensure training is sequenced appropriately relative to each resident's phase and goals.
Stay current on hiring demand and workforce trends in the sectors most relevant to Jubilee's residents and use that knowledge to shape which pathways the program prioritizes.
Build and maintain relationships with employers, apprenticeship sponsors, and credential or continuing education partners, ensuring that every pathway offered leads to real, verifiable opportunity, not just a certificate.
Develop and maintain relationships with vetted outside apprenticeship programs and credential-granting institutions (WIOA-eligible training providers, adult public charter schools, trade apprenticeships, and similar partners) as options alongside Jubilee's own practicum.
Maintain a current inventory of training programs, certifications, apprenticeships, and continuing education options relevant to residents' employment goals.
Support residents in connecting to post-pathway employment and continuing education opportunities.
Cultivate and maintain the relationship with Jubilee Farms and Jubilee Kitchen as Jubilee's own practicum sites, ensuring placements are well-structured, appropriately supervised, and genuinely developmental for residents.
Work with Farm and Kitchen leadership to ensure the work experience residents receive there is connected to the training curriculum and builds toward real employment readiness, not just task completion.
Serve as the primary point of contact between the workforce program and Farm and Kitchen leadership on staffing, scheduling, and resident readiness for placement.
Coordinate closely with the case management team to track residents' progress through the full workforce development arc, from pre-employment training through pathway completion and into employment.
Participate in regular case conferences to share observations on resident progress, flag concerns, and contribute to individual goal planning.
Maintain accurate records of resident participation, pathway placements, training completions, employment outcomes, and other workforce development milestones.
Contribute to program evaluation efforts by tracking outcomes data and participating in regular program reviews with the VP of Programs and Director of Re-Entry Programs.
Support residents in navigating challenges that arise during training and pathway participation, in coordination with case managers and housing staff.