Deputy Director, Workforce Development — Flexible Schedule

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

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.