Job Description

Location: Oakland, CA, USA 

Salary : $82,000 - $90,000 | Full-time, Exempt 

Reports to: Defy Ventures' Northern California Executive Director 

Supervises: Program Managers 

Position Overview:  

We’re looking for a mission-driven Program Director to oversee our prison and reentry programs in Northern 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  

1. Program Oversight 
2. Oversee regional implementation of both prison and post-release programs 
3. Ensure programs are delivered with consistency, structure, and care 
4. Coordinate team schedules, site logistics, and program milestones 
5. Track program sustainability, troubleshoot barriers, and drive continuous improvement 
6. Participant Engagement & Group Facilitation (prison and post-release programs) 
7. Lead group-based workshops with program participants that support emotional wellness and peer connection 
8. 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) 
9. Ensure these sessions are inclusive, healing-centered, and accessible to people from diverse backgrounds 
10. Community & Institutional Partnerships 
11. Maintain strong relationships with prison officials, parole staff, and local service providers (e.g. housing, employment) 
12. Work with employment partners and volunteers to support participant goals 
13. Represent Defy in local coalitions and community spaces 
14. Staff Supervision & Development 
15. Directly supervise 3 - 5 program staff members 
16. Provide regular coaching, observation, support, and feedback 
17. Model and reinforce trauma-informed, participant-centered approaches 
18. Build a strong, collaborative team culture 
19. Program Oversight & Grant Implementation 
20. Ensure services funded by public and private grants are delivered as promised 
21. Collaborate with Defy’s internal teams to support documentation, data collection, and evaluation 
22. 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 [Northern CA/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 Oakland, California, USA. The Program Director is expected to report to the Oakland office 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. 

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