Transitional Planner I

About the role

The Osborne Association’s ReentryWorks unit seeks a Transitional Planner I to improve reentry outcomes for individuals returning to NYC. The role assists with connecting participants to NYC services, provides logistical support on release days, and transports individuals from Hudson Valley prisons to NYC. The position is based in the Newburgh office with a hybrid schedule.

Responsibilities

• Coordinate with community service providers, the Department of Corrections and Community Supervision, and participant family members to finalize transitional plans and schedule actual community appointments.
• Assist in drafting comprehensive transitional plans for participants.
• On release day, support participants with logistics and troubleshooting, being available Monday to Thursday, 8 am–4 pm for families, DOCCS, and network providers.
• Transport participants from prison to their residences or programs in New York City.
• Provide transportation of participants, staff, or materials to programs, trainings, other offices, etc., as needed.
• Conduct motivational interviewing with participants as needed.
• Manage the ReentryWorks vehicle and arrange maintenance.
• Attend in‑person collaborations with coworkers.
• Perform other duties as assigned.

Minimum Qualifications

• High School Diploma or equivalent with at least one year of experience in social service, case management, or customer service.
• Valid New York State driver’s license and a clean driving record.

Key Competencies

• Effective communication with strong attention to detail, time management, and conflict‑resolution skills.
• Ability to work in teams and collaborate across functions.
• Willingness to travel to prisons within the Hudson Valley.
• Proficiency in Google Suite and Microsoft Office.
• Bilingual Spanish is preferred.
• Understanding of the criminal‑justice environment.

Benefits

• Four‑week vacation.
• Tuition reimbursement.
• Flexible work schedule.
• Medical, dental, and vision insurance.
• 403(b) retirement plan with company match.
• Career development through ongoing training and individual development plans.

Pay

Salary range: $26.10 – $27.81 per hour.

Schedule

Full‑time hybrid schedule: 1–2 days per week picking up participants from a nearby NYS prison and transporting them to NYC, 2 days in the Newburgh office, and the remainder remote. Availability required Monday‑Thursday, 8 am–4 pm for release‑day support.