Deputy Director, Workforce Development

Osborne Association Inc•New York, NY

10d•$80,000 - $85,000•Hybrid

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. We currently seek a full-time Deputy Director to join our Workforce Development team. Reporting out of our Brooklyn office, the Deputy Director of Workforce Development will play a key role in designing, implementing, and overseeing strategies to enhance Workforce Development programming. They will collaborate with internal and external stakeholders to leverage resources, build partnerships, and expand workforce opportunities. Additionally, the Deputy Director will ensure all program contractual obligations are met and provide supervision to direct support staff.

Requirements

Bachelor’s Degree in Criminal Justice, Public Administration or related field with three to five years of progressively responsible program management experience; in lieu of a degree High Diploma or equivalent required with at least 5 years of experience supporting a social service agency in a supervisory capacity.
Experience creating processes that enhance program performance
Knowledge of workforce development and experience supporting criminal justice impacted individuals
Experience managing both performance-based contracts and cost reimbursement contracts preferred
Strong analytical skills with the ability to collect, organize, analyze, and disseminate large amounts of data while succinctly summarizing conclusions to leadership and key stakeholders
Ability to work effectively under tight deadlines, 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
Proficiency in Microsoft Office, Google Suite, and case management software (i.e.: Salesforce, nFORM)
Strong verbal and written communication skills
Effective decision-making skills
Knowledge and understanding of the various workforce sectors
Knowledge and understanding of government contracts
Experience working with criminal justice involved individuals
Interpersonal and problem resolution skills
Strong supervisory skills

Nice To Haves

Masters Degree in social work or related fields strongly preferred.

Responsibilities

Provide direct supervision, coaching, and performance management to the Workforce Unit's Brooklyn Site Coordinator, LGBTQIA+ Case Management Program Coordinator, and CASES Career Coach, ensuring high-quality service delivery, staff accountability, and achievement of program goals.
Lead the coordination, implementation, and oversight of Workforce Development programs by providing staff with ongoing training, technical assistance, guidance, and support to ensure effective service delivery and adherence to organizational policies and funder requirements.
Develop, coordinate, and oversee recruitment, outreach, and engagement strategies to maximize participant enrollment, strengthen community partnerships, and increase program participation.
Monitor program performance through the collection, analysis, and evaluation of program data, identifying trends and implementing continuous quality improvement initiatives to enhance participant outcomes and program effectiveness.
Review, prepare and submit timely program reports, performance updates, and operational analyses to the Workforce Development Director, highlighting accomplishments, challenges, compliance status, and recommendations for improvement.
Coordinate and oversee the implementation of industry-recognized workforce training programs, including but not limited to OSHA, Site Safety Training (SST), Food Protection, and other credentialing opportunities, ensuring compliance with contractual deliverables, participant eligibility requirements, and certification standards.
Build, strengthen, and maintain collaborative relationships with funders, employers, community-based organizations, training providers, government agencies, and other key stakeholders to support program growth, participant success, and long-term sustainability.
Plan, coordinate, and facilitate regular staff meetings, individual supervision sessions, case conferences, and cross-functional planning meetings, implementing corrective actions, coaching strategies, and operational improvements as necessary.
Collaborate closely with internal departments, including Fiscal, Human Resources, Data and Evaluation, Compliance, Development, and Program Operations, to ensure seamless coordination of services and alignment with organizational priorities and strategic initiatives.
Conduct monthly program audits and quality assurance reviews to ensure compliance with organizational policies, contractual obligations, regulatory requirements, documentation standards, and best practices, while developing corrective action plans when necessary.
Coordinate and manage Workforce Development graduation ceremonies and recognition events, including developing the event "Run of Show," coordinating invitations for graduates, guest speakers, employers, funders, and internal/external stakeholders, overseeing event logistics, and ensuring successful execution of all event-related activities.
Oversee the request, inventory, distribution, and closeout of participant support goods, including OMNY cards, gift cards, and other approved incentives, ensuring fiscal accountability and compliance with organizational and funder requirements.
Ensure the timely and accurate documentation of participant support goods in the Electronic Case Management (ECM) system to support compliance, reporting, and audit readiness.
Ensure program operations consistently reflect the organization's mission, values, and strategic objectives while fostering a culture of accountability, collaboration, equity, and participant-centered service delivery.
In-person attendance is required to collaborate with co-workers
Perform other duties as assigned