Deputy Director, Workforce Development

Osborne Association; New York (NY); On-site; USD 80,000 - 85,000; Full time

Benefits offered by this job

Four weeks of vacation

Tuition reimbursement

Flexible work schedule

Medical, Dental, Vision insurance

403(b) with company match

Job summary

The Osborne Association is seeking a full-time Deputy Director of Workforce Development in Brooklyn to design, implement, and oversee workforce programs. The role supervises staff, coordinates training, and nurtures partnerships to expand opportunities for justice-involved populations.

Salary ranges from $80,000 to $85,000 per year with benefits. The position requires in-person work at the Brooklyn site and strong program management and stakeholder engagement skills.

Qualifications

• Bachelor’s degree in Criminal Justice, Public Administration or related field; 3–5 years of program management experience, or a high school diploma with 5 years in social services supervisory role.
• Masters degree in social work or related field strongly preferred.
• Experience managing performance-based and cost-reimbursement contracts preferred.

Responsibilities

• Provide direct supervision and performance management to Workforce Unit staff and ensure program goals are met.
• Lead coordination and oversight of Workforce Development programs with training and staff support.
• Develop recruitment, outreach, and engagement strategies to maximize participant enrollment.
• Monitor program performance through data collection and evaluation; drive continuous quality improvement.
• Prepare and submit timely program reports and updates to the Workforce Development Director.
• Coordinate industry-recognized training programs (OSHA, SST, Food Protection) and ensure compliance.
• Build relationships with funders, employers, community organizations, and government agencies.

Skills

Staff supervision

Program management

Data analysis

Stakeholder engagement

Budget/contract management

Relationship building

Communication skills

MS Office/Google Suite

Education

Bachelor's degree in Criminal Justice / Public Administration

Master's degree in social work or related field

High school diploma with 5 years of supervisory experience

Tools

Salesforce

nFORM

Job description

Description

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.

Salary: $80,000 - $85,000 annually

Essential Duties

• 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

Requirements

Minimum Qualifications

• 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.
• Masters Degree in social work or related fields strongly preferred.
• 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

Key Competencies

• 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

Benefits of Working at Osborne

Generous benefits include four weeks of vacation, tuition reimbursement, a 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.

The Osborne Association is an EEO/Affirmative Action employer and a VEVRAA Federal Contractor. All qualified applicants will receive consideration for employment and will not be discriminated against based on race, color, religion, sex, sexual orientation, national origin, age, disability, protected veteran status, unemployment status, or any other protected category. The Osborne Association takes affirmative action in support of its policy to advance in employment individuals who are minorities, women, protected veterans, and individuals with disabilities.

** Salary is based on commensurate experience and other qualifications.