Program Coach (Oakland)

Creating Restorative Opportunities and Programs (CROP)•Oakland, CA

5d•$36 - $39•Hybrid

About The Position

The Program Coach supports participants throughout CROP’s Ready 4 Life (R4L) program, with a focus on personal leadership development and digital literacy. The role guides participants through mindset shifts, personal responsibility, and life navigation, and provides ongoing coaching during upskilling, apprenticeships, and housing placement. The coach also delivers programming inside prisons to support personal growth, positive behavioral change, reentry preparation, and pathways into R4L. The position facilitates onboarding, leadership curriculum, digital literacy and financial wellness instruction, group and individual coaching, community engagement, and alumni support. It also leads participant admissions and recruitment, including application reviews, screenings, interviews, and outreach in correctional institutions and regional organizations. The coach maintains participant relationships and cohort culture, documents progress and outcomes, recommends program improvements, and collaborates across departments. Based in the Bay Area, this is a full-time, non-exempt, 40-hour-per-week hybrid position with regular presence in CROP’s Oakland office, weekly travel to California State Prisons, and occasional travel to the Los Angeles office. General hours are 9:00 AM–5:00 PM, Monday through Friday. The role requires compliance with prison security protocols and specialized training. The position reports to the Reentry Case Manager. The stated start date is December 15, 2026.

Requirements

Be based in the Bay Area.
Have lived experience navigating the criminal justice system and reentry process.
Have at least five years of experience in program facilitation with justice-involved populations.
Demonstrate a significant shift in thinking during incarceration, reflected in personally responsible actions, decisions, and commitment to personal growth.
Adhere to security protocols and complete specialized training for work within California State Prisons.

Nice To Haves

Understanding of the reentry process and the role of personal development, behavioral change, and leadership growth in successful reintegration.
Familiarity with institutional culture within California State Prisons and ways to navigate and transform it to foster growth and reentry readiness.
Experience in one-on-one coaching that supports mindset shifts, personal responsibility, and life navigation, with the ability to adapt strategies to individual needs.
Experience delivering personal development curricula, including digital literacy and financial wellness, to diverse groups.
Experience identifying candidates for transformative programming, leading admissions processes, and promoting program enrollment inside prisons.
Proficiency in tracking and documenting participant progress, measuring success, and providing data-driven feedback for continuous improvement.
Empathy and emotional intelligence in supporting justice-involved individuals and building trust.
Ability to adapt and maintain a positive, supportive presence in challenging, high-pressure environments such as correctional facilities.
Skill in building meaningful, lasting relationships with participants, peers, and stakeholders.

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 distribution of application materials.
Build and maintain relationships with participants and establish clear norms, values, and 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 support 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 projects and initiatives.
Coach participants on setting and achieving personal development goals, implementing positive behavioral changes, and navigating practical aspects of reentry.
Lead workshops and activities that build practical reentry skills and create a forward-looking institutional 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.