Sr. Director, National Workforce and Reentry

Location: Remote (must reside within CA, WA, UT, IL, NY, NJ, CT, or PA) or hybrid for candidates within 40 miles of our Los Angeles headquarters (one day per week in Koreatown office)

Reports to: Chief Program Officer

Position Type: Full-time, Exempt

Salary: $105K - $115K

The Opportunity

Defy Ventures Sr. Director of National Workforce and Reentry will ensure that graduates of our 8-10 month in-custody program (CEO of Your New Life) are fully supported in their post-release reentry journey through access to case management and economic opportunity. The position leads two significant program components.

The first is ownership of the design, standards, and quality of the Career and Reentry pathway, which supports participants through their first year of reentry. This includes providing technical support for field-based Career and Reentry managers, who deliver pre-release coaching inside correctional facilities, structured individual action planning, system and resource navigation, and workforce development after release.

The second is leading the design and build of our new Workforce and Training Continuum Model (WTCM). This includes developing industry-recognized credentials tied to in-prison coursework, relevant partnerships, a structured career pathway for peer leaders who facilitate inside correctional facilities, and navigation systems connecting graduates to postsecondary education, licensing, apprenticeships, traditional employment, or Defy's Business Bootcamp for those further pursuing entrepreneurship.

The role works as an integrated pair with the Sr. Director of National Prison Programs (CEO of Your New Life). The two share a weekly national meeting cadence with local chapter managers and co-design its content. This role also carries responsibility for program iteration, investigating design challenges as directed by the Chief Program Officer, developing solutions, and contributing informed recommendations about where the program should evolve.

Key Responsibilities

Post-Release Program Design and Standards

• Own and maintain the standard operating procedures and standards for the Career and Reentry pathway, covering the full sequence from initial contact through the first year of support.
• Provide coaching to Career and Reentry managers on system navigation, including questions related to supervision compliance, housing, employment, legal services, healthcare, and community-based referrals.
• Build and maintain rubrics measuring operational execution, including timely completion of core activities, documentation quality, and referral follow-through.
• Onboard new staff on the program model, the coaching approach, and the application of the organization's well-being framework in their practice.
• Ensure consistent delivery of pre-release touchpoints conducted inside correctional facilities ahead of participant release.

Workforce Development and Credentialing

• Design a portable credentialing framework with educational partners that translates in-prison program learning into competency-based credentials recognized by employers and postsecondary institutions.
• Develop a credentialing system and career pathway for Defy peer facilitators that converts competencies gained through in-prison facilitation to transitional paid employment opportunities with Defy Ventures.
• Build navigation systems connecting graduates to postsecondary education, licensing, apprenticeships, and employment in high-growth industries.
• Develop employer and industry partnerships that create meaningful hiring pathways for program graduates.

Operational Support and Collaboration

• Coordinate with field leadership and the operations team to resolve data gaps, documentation issues, and tool or system needs as they arise.
• Investigate program design challenges at the direction of the CPO and contribute recommendations on where the program should evolve, grounded in field-level evidence and operational data.
• Co-design and co-facilitate the weekly national meeting cadence with the Sr. Director of Prison Programs. Maintain close working knowledge of in-prison program content, particularly as it relates to credentialing and workforce pathway design.
• Collaborate with a part-time consultant who provides specialized expertise in trauma-informed coaching methodology and well-being-focused program design.

Qualifications

Required

• Bachelor's degree or equivalent combination of education and relevant experience.
• At least 3 years of program management in a nonprofit or mission-driven organization.
• 1 to 2 years of program design experience, including development or iteration of program models, operational procedures, or quality systems.
• At least 3 years of experience leading workforce development programming including stewardship of relationships with educational institutions or employer and licensing partners.
• At least 2 years of case management experience in a reentry, social services, or community-based setting.
• Working knowledge of trauma-informed practice and how it shapes program design and staff development.

Strongly Preferred

• Lived experience with the justice system, or sustained professional experience with justice-impacted communities.
• Background in career pathway design or credentialing programs serving underrepresented populations.
• Familiarity with post-release services, reentry coaching, or community-based case management models.

Location and Travel

Depending on location, this may be a hybrid (one day per week in office) or remote position. Candidates must reside in a state where Defy operates: California, Washington, Utah, Illinois, Pennsylvania, or the Tri-State area (NY/NJ/CT). Candidates within 40 miles of Defy's Los Angeles headquarters are expected in the office one day per week.

About Us

Defy Ventures is an entrepreneurship, employment, and personal development training program that recognizes the potential in many formerly and currently incarcerated people to become successful, legal entrepreneurs. Entrepreneurs in Training (EITs) “defy the odds” through our program, which includes intensive leadership development, Shark Tank-style business pitch competitions,and executive mentoring. We work to address injustice through our commitment to changing perceptions, breaking cycles of recidivism, and helping people to create equity in historically marginalized communities.

Defy Ventures is an equal opportunity employer. Defy Ventures uses E-Verify to confirm the employment eligibility of all new hires in the United States. All applicants will be considered for employment without attention to race, color, religion, sex, sexual orientation, gender identity, national origin, veteran,or disability status.

Comprehensive health benefits

15 days of paid vacation annually

401k, sick time, parental leave