Director, Prison and Reentry Programs (Los Angeles, CA)

Position Overview:

We’re looking for a mission-driven Program Director to oversee our prison and reentry programs in Southern California. This role will lead a small regional team and ensure that those returning from incarceration receive consistent, trauma-informed support from the moment they begin programming in prison to their first year home.

The Program Director will oversee two core programs within the region:

• CEO of Your New Life (CEO YNL): A 7-10 month course inside select California prisons that uses entrepreneurship as a foundation to explore identity, mindset, leadership, and reentry planning
• Career & Reentry (C&R): A post-release program that builds on the prison experience to help people stabilize after release and pursue long-term goals through reentry coaching, housing support, well-being programs, and continued personal development.

This is a high-impact role for someone who believes in dignity, healing, and second chances, and wants to help create systems that support people coming home from incarceration in real and lasting ways.

Key Responsibilities

Program Oversight

1. 1. Oversee regional implementation of both prison and post-release programs
   2. Ensure programs are delivered with consistency, structure, and care
   3. Coordinate team schedules, site logistics, and program milestones
   4. Track program sustainability, troubleshoot barriers, and drive continuous improvement

Participant Engagement & Group Facilitation (prison and post-release programs)

1. 1. Lead group-based workshops with program participants that support emotional wellness and peer connection
   2. Facilitate Defy’s peer support groups that help participants build resilience, manage stress, and process the challenges of reentry, both in prisons (in person) and in the community (in person and virtual)
   3. Ensure these sessions are inclusive, healing-centered, and accessible to people from diverse backgrounds

Community & Institutional Partnerships

1. 1. Maintain strong relationships with prison officials, parole staff, and local service providers (e.g. housing, employment)
   2. Work with employment partners and volunteers to support participant goals
   3. Represent Defy in local coalitions and community spaces

Staff Supervision & Development

1. 1. Directly supervise 3 - 5 program staff members
   2. Provide regular coaching, observation, support, and feedback
   3. Model and reinforce trauma-informed, participant-centered approaches
   4. Build a strong, collaborative team culture

Program Oversight & Grant Implementation

1. 1. Ensure services funded by public and private grants are delivered as promised
   2. Collaborate with Defy’s internal teams to support documentation, data collection, and evaluation
   3. Help maintain clear records of participant progress and program impact

Qualifications

Required:

• Master’s Degree in Social Work (MSW)
• 3+ years of experience in direct service or program implementation
• 2+ years of experience supervising or leading a team
• Strong understanding of the challenges and opportunities involved in reentry
• Experience facilitating group discussions or workshops, especially with system-impacted communities
• Excellent communication, problem-solving, and organizational skills
• Drivers License and ability to travel to multiple sites around the Southern CA region (by car), including prisons and community program locations
• Ability to be cleared at CDCR institutions

Preferred:

• Experience with Housing First program model a plus
• Lived experience with incarceration or direct connection to affected communities
• Training in motivational interviewing, harm reduction, or similar approaches

Work Environment & Travel Requirements

This is a hybrid position based in Southern California. The Program Director is expected to report to the Los Angeles office in Koreatown a minimum of two days per week and is otherwise permitted to work remotely, as schedule permits. Regular other in-person responsibilities include:

• Visiting state prisons to support in-prison programming
• Attending community-based programming and partner meetings
• Supervising and supporting team members at different sites within the region
• Participating in occasional team retreats or trainings

Reliable transportation is required, and travel will occur multiple times per month across the region. Some evening or weekend availability may be necessary depending on program needs and institutional schedules.

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.