Sr. Director, National Reentry & Well-Being Programs

Location: Remote (US Based)

Reports to: Vice President of National Programs

Salary | Position Type: $110,000-$120,000, Full-time, Exempt

About the Role:

The Sr. Director of National Reentry & Well-Being Programs is a key member of Defy Ventures’ leadership team, responsible for shaping and advancing the organization’s reentry strategy. This leader will ensure that participants are not only welcomed home, but also supported through a seamless continuum of care that begins inside correctional facilities and extends into community reentry, providing the resources and guidance needed to build stable, thriving lives.

This position requires a unique blend of program leadership, clinical expertise, and practical experience in reentry. The Sr. Director will oversee Defy Ventures’ national Career and Reentry programs, safeguarding quality and consistency across sites while keeping the participant experience at the center. They will mentor and develop staff to move beyond transactional service delivery, fostering a culture of proactive system navigation, solution-building, and transformational care.

Additionally, the Sr. Director will lead the rollout of new California-based housing supports funded by a recently awarded major grant, ensuring that growth and scale are matched by fidelity to trauma-informed practices. Above all, this role ensures that Defy Ventures’ reentry pathway, from inside to outside, reflects and reinforces the dignity, agency, and resilience of every participant we serve.

Please Note: This is a remote position, but candidates must reside in a state where Defy Ventures operates an active chapter: California, Washington, Utah, Illinois, Pennsylvania, or the Tri-State area (NY/NJ/CT). For staff located within 45 miles of Defy Ventures’ headquarters (Koreatown, Los Angeles), this position is hybrid, (work from the office one day per week, work from home up to 4 days). For staff located outside that radius, this position will be fully remote

Key Responsibilities

Reentry Program Leadership & Design

• Oversee and support the inside-to-outside program model, ensuring continuity of care for participants as they transition from prison-based programming to community reentry services, with a consistent trauma-informed approach.
• Lead the ongoing improvement of Defy Ventures' reentry and well-being programs across all chapters.
• Ensure all services and programs are grounded in research-based reentry frameworks and best practices.
• Support partnership development with other reentry providers, employers, and mental health networks to expand opportunities for participants.

Mental Health & Well-Being

• Oversee Defy Ventures’ peer support groups, well-being workshops, and counseling partnerships such as BetterHelp to ensure participants have reliable spaces for connection and support.
• Improve program materials, training for staff, and development of supplemental learning resources for participants both inside prison and after release.
• Develop and refine resources that make mental health support accessible and stigma-free for participants.

Staff Development & Coaching

• Train and mentor Career & Reentry Managers to adopt a transformational approach, serving as system navigators, advocates, and bridge builders.
• Provide coaching on motivational interviewing, case management, and barrier removal strategies.
• Support site leadership in onboarding new program staff.
• Serve as both a consultant and a quality steward for local chapter program leaders, regularly advising on best practices while establishing and enforcing national program expectations.

Grant & Compliance Alignment

• Translate relevant grant requirements into clear workflows and tools that staff can implement effectively.
• Collaborate with data and systems staff to ensure accurate and timely tracking.
• Ensure all services meet compliance and evaluation standards while remaining participant-centered.

Evaluation & Learning

• Use data and participant feedback to refine program design and staff training.
• Partner with external evaluators and internal teams to track outcomes in housing, employment, and well-being.

Qualifications

Required:

• Minimum Master’s degree in Social Work (MSW);
• Minimum 4 years of progressive leadership experience in reentry or human services.
• Proven ability to design and scale trauma-informed, person-centered programs.
• Strong background in coaching and developing frontline staff.
• Experience building partnerships across housing, mental health, and reentry ecosystems.

Preferred:

• Lived experience of incarceration, or deep professional experience with justice-impacted communities.
• Experience implementing housing-first or similar evidence-based approaches.

Travel Requirements

• Occasional travel to program sites

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.