Program Coach (Oakland)

CROP•Oakland, CA

5d•Hybrid

About The Position

CROP (Creating Restorative Opportunities and Programs) is an Oakland-based 501(c)(3) nonprofit focused on reentry through education, advocacy, housing, personal leadership development, and workforce pathways. The Program Coach supports participants in CROP’s Ready 4 Life (R4L) program, emphasizing personal leadership development and digital literacy. The role coaches participants through mindset shifts, personal responsibility, and life navigation, including during upskilling, apprenticeships, and housing placement. It also delivers programming inside prisons to support personal growth, reentry readiness, and pathways into R4L. The Program Coach facilitates onboarding and curriculum, provides individual and group coaching, and supports participant recruitment, admissions, and screening. The role travels weekly to California State Prisons and also requires regular presence in the Oakland office, with occasional travel to the Los Angeles office. The position is full-time, non-exempt, hybrid, and 40 hours per week, generally Monday through Friday from 9:00 AM to 5:00 PM. It requires adherence to security protocols and specialized training for work in California State Prisons. The role is supervised by the Reentry Case Manager.

Requirements

Be based in the Bay Area.
Have lived experience navigating the criminal justice system and reentry process.
Have 5 or more years of experience in program facilitation with justice-involved populations.
Demonstrate a significant shift in thinking during incarceration, reflecting a personally responsible perspective through actions, decisions, and commitment to personal growth.
Understand the reentry process and the role of personal development, behavioral change, and leadership growth in successful reintegration.
Be familiar with institutional culture within California State Prisons and how to navigate and transform it to foster growth and reentry readiness.
Have experience in one-on-one coaching and mentoring, including supporting mindset shifts, personal responsibility, and life navigation.
Have experience delivering personal development curricula, including digital literacy and financial wellness, to diverse groups.
Have experience identifying candidates for transformative programming, leading admissions processes, and engaging with people inside prisons to promote enrollment.
Be proficient in tracking and documenting participant progress, measuring success, and providing data-driven feedback.
Demonstrate empathy and emotional intelligence when supporting justice-involved individuals and building trust.
Be able to adapt in high-pressure environments such as correctional facilities while maintaining a supportive presence.
Be skilled at building lasting relationships with participants, peers, and stakeholders.
Complete specialized training and follow security protocols for working within California State Prisons.
Submit a resume and cover letter.

Responsibilities

Facilitate CROP’s 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 group and one-on-one coaching throughout the program, supporting personal leadership development and behavioral change.
Lead community engagement activities and hands-on learning experiences, including community events and service projects.
Facilitate postgraduate support, including virtual Alumni Support meetings as needed.
Lead the R4L admissions process, including reviewing applications, conducting initial screenings, and interviewing potential participants.
Recruit participants within correctional institutions and regional organizations through information sessions, individual conversations, and application materials.
Build and maintain relationships with participants, establish clear norms and values, and foster a supportive cohort culture.
Ensure adherence to program schedules and collect and implement participant feedback to improve program delivery.
Travel weekly to California State Prisons to deliver personal development curriculum and foster leadership growth and reentry readiness.
Visit the Los Angeles office at least twice a year or for up to 10 work days annually to connect with team members and contribute to shared initiatives.
Coach participants on setting and achieving personal development goals, making positive behavioral changes, and navigating practical aspects of reentry.
Lead workshops and activities that build practical reentry skills and foster 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 for program evaluation and organizational reporting.
Participate in cross-departmental initiatives that strengthen CROP’s programs and impact.
Model CROP’s values and contribute to a positive organizational culture in interactions with participants, colleagues, and partners.
Perform other duties as assigned to support organizational goals and participant success.