Deputy Director

The Osborne Association serves individuals, families, and communities affected by the criminal justice system. Through our programs, we offer opportunities for people to heal from and repair harm, restore their lives, and thrive. We challenge systems rooted in racism and retribution and fight for policies and practices that promote true safety, justice, and liberation.

At Osborne, we are guided by core values and shared beliefs. We honor everyone's capacity to change, celebrate our shared humanity, are united in our pursuit of justice and equity, take all possible steps to keep our commitments, and advocate for people and principles with fierce and tenacious determination.

The Osborne Association seeks a Deputy Director to join our Workforce Development team, supporting our new Trauma‑Informed Care Program. The Deputy Director will oversee the daily operations of the program on Rikers Island, ensuring that all programmatic and contractual goals are met. This role supervises staff, monitors performance and outcomes, and ensures high‑quality service delivery. The Deputy Director collaborates closely with Department of Correction (DOC) partners and subcontractors to maintain strong program performance, compliance, and timely, accurate reporting and data submission.

This is an on‑site position reporting from the Department of Correction’s Rikers Island, with occasional attendance required at our Brooklyn office. Occasional evening or weekend hours may be required as well.

Salary Range: $80,000 – $85,000 annually

• Support the Program Director in ensuring all program contractual obligations are fulfilled.
• Participate in the development of program activities and continually evaluate the quality of services provided.
• Develop systems and procedures to ensure compliance with program requirements.
• Collaborate daily with DOC staff across facilities to ensure strong relationships and open communication.
• Manage subcontractor relationships to ensure smooth service delivery, coordinated scheduling, and consistent invoicing.
• Directly supervise Trauma‑Informed Care Specialists and Program Assistant to ensure effective service delivery and program success. Provide weekly supervision to each staff member and lead team meetings. Interview and hire for vacancies as needed.
• Coordinate staff scheduling to ensure smooth program operations, making adjustments as needed to enhance performance and efficiency.
• Facilitate groups as needed to ensure full coverage during staff vacancies or absences.
• Oversee case conferences, providing staff with opportunities to share assessments, observations, and follow‑up activities for participants on their caseloads.
• Ensure that staff effectively develop, define, and implement agreed‑upon treatment or service plans for all participants, aligning services with their individual needs, goals, and circumstances. This includes monitoring progress, making necessary adjustments, and ensuring that all interventions and support strategies are delivered in a structured, consistent, and impactful manner.
• Research best practices in trauma‑informed care and suggest new curricula or modalities to supplement program services.
• Organize and facilitate virtual and/or in‑person training sessions for program staff to enhance their knowledge, strengthen their skills, and support their ongoing professional development.
• Actively participate in interdepartmental and external stakeholder meetings, including those held at Department of Corrections facilities (such as Rikers Island and other New York City/County jails), to increase awareness of program services and strengthen partnerships that support successful reintegration efforts.
• Participate in supervision meetings with the Director of Workforce Development.
• Ensure accurate data entry for all program activities in both DOC database and internal Salesforce database. Prepare reports and other documentation to ensure compliance with the program’s requirements.
• Attend assigned trainings.
• In‑person attendance at Rikers Island is required daily.
• Perform other duties as assigned.

• Master’s…