Deputy Director of Prison Services

Osborne Association Inc • City of Newburgh, NY

8d • $80,000 - $82,000 • Onsite

About The Position

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 Deputy Director will provide strategic leadership and operational oversight for in-prison transitional planning services, specifically managing programs based out of the Newburgh office that serve individuals across state DOCCS facilities. This role ensures high-quality discharge planning, effective community engagement, and adherence to evidence-driven practices.

Requirements

• Bachelor’s Degree in Human Services, Public Administration, Criminal Justice, Social Work or a related field.
• A minimum of 5 years of progressive experience in a social service agency providing direct service care, with
• A minimum of 3 years of experience managing and coaching a team
• Extensive knowledge of working in correctional settings, specifically NYS DOCCS, is strongly preferred.
• Demonstrated ability to lead multidisciplinary teams.
• Proficient in Google Suite or Microsoft Office.
• Ability to obtain and maintain clearance to work in New York State prisons.
• Must be able to travel locally and to assigned New York State prison facilities.
• Competence within the criminal justice environment and social service processes.
• Excellent assessment, treatment planning and conflict resolution skills.
• Effective oral and written communication skills.
• Ability to analyze and integrate information independently.
• Exceptional database management skills.
• Proficiency in Microsoft Office and/or Google Suite.
• Ability to work effectively under tight deadlines, pay strong attention to detail, and time management skills.
• Ability to work in teams and collaborate effectively with people in different functions.
• Ability to take the initiative and drive for results.
• Ability to communicate with all levels of the organization and build strong relationships.

Responsibilities

• Supervise and support the Program Coordinators for ReentryWorks (RW), Queensboro (QB), Corrections Health Initiative (CHI), and the Elder Reentry Initiative (ERI).
• Supervise and assist direct reports with career development by providing guidance and identifying training opportunities.
• Supervise staff providing individual case management services, including coordinating with community and correctional partners and other stakeholders.
• Provide direct services as needed, including visiting prison sites several times a month.
• Oversee the creation of comprehensive transition plans for individuals in approximately 28 state prisons, ensuring plans include needs assessments and collaboration with DOCCS.
• Keep abreast of the latest information about HIV/AIDS, Hepatitis, and other co-infections.
• Coordinate with Osborne and correctional health staff to recruit participants and obtain necessary documentation.
• Manage all aspects of program operations, including monitoring performance against annual targets.
• Collaborate with the Vice President of Prison Services to establish contract goals, objectives, and work plans for each program.
• Implement work activities to meet goals; monitor and evaluate the effectiveness of results.
• Oversee participant case management, release-day transportation logistics, transitional planning, coordination with DOCCS and participant families, and coordinating with community and corrections providers to ensure smooth transitions into the community.
• Maintain contract requirements and internal program objectives, ensuring that services are delivered with fidelity to evidence-based models like Motivational Interviewing and Trauma Informed Care.
• Ensure all contract deliverables are met.
• Adhere to established DOCCS and Osborne guidelines for operating prison and community reentry programs.
• Lead program improvements, such as merging safety plans across units, completing staff evaluations, and developing new resources for gaps in service.
• Responsible for maintaining and improving data collection and reporting processes; regularly reviews caseload volume and case progression to inform coaching and management decisions.
• In collaboration with the Data Analyst, ensure that record keeping and reports are accurate and timely.
• Build and maintain mutually beneficial relationships with DOCCS’ facility leadership, Osborne staff, and external community partners to ensure wrap-around services and coordinated referrals.
• Actively engage with funders and referral sources to maintain positive working relationships.
• Ensure a welcoming environment for all participants.
• Attend and participate in case conferences with Parole.
• Establish and maintain contacts with community-based organizations.
• In-person attendance is required to collaborate with co-workers as well as in-facility work.
• Must undergo a background check, and obtain and maintain a DOCCS volunteer clearance at all times.
• Perform other duties as assigned.

Benefits

• Generous benefits include four weeks of vacation, tuition reimbursement, flexible work schedule, excellent Medical, Dental, and Vision insurance, and a 403(b) plan with a company match. Career development through ongoing training and individual development plans.

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Number of Employees: 251-500 employees