Sr. Director, National Prison Programs

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' in-prison program, CEO of Your New Life, is an 8-10 month cohort-based program that prepares currently incarcerated individuals for sustainable reentry. The program is grounded in the Well-Being Development Model for Reentry, founded by Dr. Carrie Pettus-Davis, and uses entrepreneurship as the primary vehicle for skill development.

The Sr. Director, National Prison Programs owns the design, standards, and quality of implementation across all three in-custody program models: adult prison, transitional facility, and juvenile. The role carries authority over the operational frameworks that govern program delivery and the training systems that prepare facilitators to deliver effectively. Field program staff report through a separate management chain. This role defines the standards they are held to and provides the coaching and training required to meet them.

The work spans both systems and practice. It includes maintaining operational documents, pacing frameworks, and quality benchmarks across dozens of sites, and it requires regular presence inside correctional facilities to observe sessions and identify training improvements. The role also contributes to program iteration, investigating design and curriculum challenges for consideration by the Chief Program Officer and VP, Learning, as well as contributing informed recommendations about where the program should evolve.

This Sr. Director works as an integrated pair with a counterpart who leads Defy Ventures post-release and workforce development programming. The two roles share a weekly national meeting cadence and co-design its content.

Key Responsibilities

Program Standards and Operational Oversight

• Own and maintain the standard operating procedures for all three program models, ensuring alignment with current design and usability for field staff.
• Maintain and update program management tools and systems for standardized implementation across the country
• Define and document the conditions required for successful program implementation at each site.
• Develop and maintain the operational tools, templates, and dashboards that support program delivery from launch through closeout.

Training and Quality

• Design and deliver facilitator training on curriculum delivery, including structured observation cycles, feedback protocols, and quality benchmarks. Curriculum content is owned by a separate learning and development function.
• Train and develop peer facilitators on expectations, facilitation quality, and their contribution to the learning environment.
• Build and maintain standardized rubrics for participant deliverables, ensuring consistent assessment of reflection, comprehension, and application across cohorts and sites.
• Establish and communicate program quality benchmarks across all three models.
• Provide ongoing coaching to field program staff on delivery standards through a weekly national meeting cadence and additional touch points.

Implementation Support and Field Presence

• Coordinate with field leadership to resolve data gaps and documentation issues identified by the operations team.
• Identify tool and system needs and engage the appropriate internal teams to address them.
• Conduct regular site visits, at 2x per quarter, to observe live sessions and maintain direct connection to the experience of in-facility delivery. These visits may require overnight travel.

Program Iteration and Collaboration

• Investigate program design challenges at the discretion of the CPO, gathering field-level evidence and developing proposed solutions for review.
• Contribute informed observations about program performance and recommend areas for design attention.
• Co-design and co-facilitate the weekly national meeting cadence with the Sr. Director of Workforce and Reentry Programs.
• Provide subject-matter input to support credentialing and workforce pathway development led by the counterpart role.

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.
• At least 1-2 years of program design experience at scale, including developing or iterating on program models, operational procedures, or quality systems across multiple sites.
• At least 1 year experience training facilitators, or substantial direct experience facilitating with large groups.
• Experience coaching or developing staff outside of a direct supervisory relationship.
• Working knowledge of trauma-informed practice and how it shapes program design and staff development.
• Driver’s License and reliable vehicle

Strongly Preferred

• Lived experience with the justice system, or sustained professional experience with justice-impacted communities.
• Experience working in or alongside correctional facilities, transitional settings, or other institutional environments.
• Understanding of group dynamic development and adult learning.

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. The role expects at minimum two facility visits per quarter in some cases potentially requiring overnight stay. Up to 10% travel per year during swell programming years.

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 inTraining (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