Program Coach (Oakland)

CROP•Oakland, CA

10h•Hybrid

About The Position

The Program Coach plays a key role in supporting participants throughout CROP’s Ready 4 Life (R4L) program, focusing on personal leadership development and digital literacy. This position involves guiding participants through mindset shifts, personal responsibility, and life navigation while providing ongoing coaching during key program phases, including upskilling, apprenticeships, and housing placement. A key responsibility of the Program Coach is delivering CROP’s programming inside prisons to help transform institutional culture, prepare individuals for successful reentry, and create pathways into the Ready 4 Life program. Through these efforts, the Program Coach fosters personal growth, promotes positive behavioral change, and helps participants successfully transition back into their communities. In addition to individualized coaching, the Program Coach leads program presentations within institutions, supports applicant recruitment, and participates in the applicant screening process. This role is critical to fostering participant growth and ensuring successful program engagement.

Requirements

Based out of Bay Area
Lived experience navigating the criminal justice system and reentry process
5+ years experience in program facilitation with justice-involved populations
Demonstrate a significant shift in their thinking during their incarceration, reflecting a personally responsible perspective through their actions, decisions, and commitment to personal growth
Knowledge of Reentry and Personal Development: A strong grasp of the reentry process and how personal development, behavioral change, and leadership growth are crucial for successful reintegration into society.
Familiarity with Correctional Systems: Knowledge of institutional culture within California State Prisons and how to navigate and transform it to foster growth and readiness for reentry.
Coaching and Mentoring: Experience in one-on-one coaching to guide participants through mindset shifts, personal responsibility, and life navigation. Ability to offer ongoing support and adjust coaching strategies to meet individual needs.
Curriculum Design and Delivery: Experience delivering personal development curricula, including digital literacy and financial wellness, to a diverse group of individuals.
Recruitment and Screening: Prior experience with identifying high potential candidates for transformative programming, leading admissions processes, and engaging with individuals inside prisons to promote program enrollment.
Data Management and Reporting: Proficient in tracking and documenting participant progress, measuring success, and providing data-driven feedback for continuous improvement.
Empathy and Emotional Intelligence: Ability to understand and relate to the personal struggles and aspirations of justice-involved individuals, providing compassionate support and fostering trust in the coaching relationship.
Adaptability in High-Pressure Environments: Ability to thrive in challenging environments, such as correctional facilities, and adapt quickly to changing circumstances while maintaining a positive and supportive presence.
Relationship Building: Skilled in cultivating meaningful, long-lasting relationships with participants, peers, and stakeholders, ensuring continued engagement and support throughout the program.

Nice To Haves

Travel to the LA office at least twice a year or up to 10 work days annually to connect with team members and contribute to shared projects and initiatives

Responsibilities

Facilitate CROP’s signature three-day onboarding seminar and orientation for new participants
Deliver CROP’s three-month Leadership 4 Life curriculum
Support digital literacy and financial wellness instruction
Provide both group and 1:1 coaching throughout the program’s duration, supporting personal leadership development and behavioral change
Lead community engagement activities and hands-on learning experiences—such as community events and service projects—that foster personal growth, promote contributing to others, and instill a sense of responsibility and gratitude toward the broader community.
Facilitate postgraduate support, including virtual Alumni Support meetings as needed
Lead the admissions process for R4L candidates, including reviewing applications, conducting initial screenings, and interviewing potential participants
Recruit program participants within correctional institutions and regional organizations through information sessions, one-on-one conversations, and distributing application materials
Build and maintain relationships with program participants, establishing clear norms, values, and a supportive cohort culture
Ensure adherence to program schedules while collecting and implementing participant feedback to continuously improve program delivery
Travel weekly to California State Prisons to deliver CROP’s personal development curriculum, fostering leadership growth and reentry readiness.
Coach participants on setting and achieving personal development goals, implementing positive behavioral changes, and successfully navigating the practical aspects of reentry
Lead workshops and activities that build practical reentry skills, changing institutional dynamics by creating a forward-looking environment focused on successful community return
Document participant progress, including learning component scores, attendance, and individual metrics
Provide regular reports on participant outcomes and recommend program improvements to the Managing Director
Maintain accurate records to support program evaluation and organizational reporting
Participate in cross-departmental initiatives that strengthen CROP's overall program offerings and impact
Contribute to a positive organizational culture by modeling CROP's values in all interactions with participants, colleagues, and partners
Perform other duties as assigned to support organizational goals and participant success