Program Coach (Oakland)

CROP Organization; Oakland (CA); On-site; USD 42,000 - 58,000; Full time

Job summary

CROP Organization in Oakland is seeking a Program Coach to support participants in the Ready 4 Life program, guiding personal leadership development, digital literacy, and life navigation during onboarding, upskilling, apprenticeships, and housing placement.

The role includes delivering programming inside California state prisons, leading workshops, recruiting and screening applicants, and providing 1:1 coaching and group sessions to foster growth, accountability, and successful community

Job description

Program Coach (Oakland)

Full-Time Position
Start Date: December 15, 2026

Who We Are

CROP (Creating Restorative Opportunities and Programs) is an Oakland-based 501(c)(3) nonprofit dedicated to reimagining reentry through a holistic and human-centered model. Driven by innovative approaches to education, advocacy, housing, personal leadership development, and workforce pathways, CROP works to reduce recidivism and create opportunities for justice-impacted individuals. Founded by leaders with direct lived experience in the criminal justice system, CROP’s programs aim to transform lives and communities.

What You’ll Do

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.

OAKLAND PROGRAM DELIVERY AND COACHING

• 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

PROGRAM PARTICIPANT RECRUITMENT AND SUPPORT

• 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

PERSONAL DEVELOPMENT AND COACHING IN CALIFORNIA STATE PRISONS

• Travel weekly to California State Prisons to deliver CROP’s personal development curriculum, fostering leadership growth and reentry readiness. This includes visits 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

• 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

PROGRAM EVALUATION AND REPORTING

• 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

TEAM COLLABORATION AND ORGANIZATIONAL CULTURE

• 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

Who You Are

You excel in collaborative environments, driven by your deep understanding of accountability and a people-centered