Director, Career Advancement & Retention

Position Summary 

The Director, Career Advancement & Retention leads OBT’s agencywide alumni engagement, employment retention, and career advancement initiatives across training tracks, while serving as the dedicated Job Developer for program alumni. The Director sets strategy, designs and delivers programming, develops employer and community partnerships, directly provides alumni employment services, and oversees performance and continuous improvement. The role collaborates with industry-aligned Job Developers to leverage existing job orders and sector expertise without replacing their responsibilities. Designated service members, interns, and support personnel assist with administrative and implementation tasks under the Director’s day-to-day project guidance and applicable supervisory agreements. 

Essential Job Functions and Responsibilities 

Alumni Engagement, Communications & Events 

• Lead alumni engagement and re-engagement strategies for current and prior-year graduates, including employed, underemployed, unemployed, and disconnected alumni. 

• Plan, promote, host, and evaluate in-person and virtual hiring events, employer recruitment sessions, resource fairs, job readiness workshops, networking events, professional development panels, and related alumni initiatives; coordinate participating employers, partners, and speakers. 

• Personally design event flyers, email campaigns, invitations, text messaging, and other outreach materials, direct approved distribution, registration, reminders, attendance tracking, and post-event follow-up through support personnel. 

• Develop alumni network opportunities, including peer connections, mentorship, and professional development activities informed by graduate and labor-market needs. 

Direct Job Development & Career Advancement 

• Serve as the dedicated Job Developer for alumni, directly conducting employment intake and assessment, career coaching, resume and interview preparation, candidate screening, employer referrals, placements and re-placements, employment verification, and advancement planning. 

• Maintain employer relationships and identify hiring, apprenticeship, and training opportunities across healthcare, technology, construction, skilled trades, business services, and emerging sectors. 

• Coordinate with Job Developers serving Pharmacy Technician, Construction, HVAC, Masonry, Digital Marketing, HHA/ESOL, HSE/GED, technology, and other training tracks to share job orders, streamline referrals, and avoid duplicated outreach. 

• Help alumni address job loss, short tenure, barriers to retention, career transitions, and wage advancement through individualized strategies and relevant referrals. 

• Meet an individual placement target established with leadership that appropriately reflects both direct-service and director-level responsibilities. 

Employment Retention, Data & Quality Assurance 

• Direct 90-, 180-, 270-, and 365-day retention milestone protocols, monitor at-risk situations, and lead targeted re-engagement and job-retention interventions. 

• Collaborate with the Chief Impact Officer, Salesforce Administrator, and authorized support teams to define retention dashboard needs, improve Salesforce workflows, verify records, and monitor data quality; leave system configuration to authorized personnel. 

• Oversee accurate documentation of participant contacts, employment outcomes, verification materials, and service activity in both Salesforce and Outcomes (for all alumni with complete JtBO applications). Lead administrative duties relative to the establishment of electronic records for all alumni in alignment with JtBO contractual expectations in SharePoint. 

• Analyze alumni engagement, placement, and retention trends across programs and employers; deliver performance reports, findings, and recommendations to leadership and funders as requested. 

• Maintain participant confidentiality, accurate eligibility documentation, and compliance with OBT policies and applicable funder requirements. 

Project Leadership & Support Personnel 

• Lead the day-to-day work plans and delegated projects of assigned AmeriCorps members, partner-agency interns, and other support personnel, including event registration, intake logistics, outreach administration, scheduling, partner-contact lists, record updates, document coordination, and resource distribution. 

• Provide onboarding, task guidance, regular project check-ins, coaching, and review of deliverables for quality and timeliness. 

• Coordinate with OBT leadership on service requirements, approved duties, performance processes, and any needed authorization for role changes. 

• Create sustainable operating procedures, reusable templates, contact records, and transition plans for continuity across personnel rotations. 

Partnerships & Cross-Functional Coordination 

• Represent OBT and expand relationships with employers, Workforce1, community organizations, government agencies, schools, training providers, and resource partners to improve alumni employment and advancement options. 

• Coordinate with training teams, case management, program-track Job Developers, executive leadership, and external partners to align alumni opportunities, address employment barriers, and strengthen service delivery. 

Knowledge, Skills and Abilities 

• Ability to lead cross-functional workforce initiatives, delegate assignments, coach personnel, and deliver measurable engagement, placement, and retention outcomes. 

• Strong skills in employer relations, career coaching, labor-market navigation, event facilitation, community partnerships, and alumni outreach communications. 

• Experience with Salesforce/PTS or comparable CRM and participant-tracking systems, performance analysis, reporting, and documentation of quality assurance. 

• Excellent communication, project management, relationship-building, problem-solving, and organizational skills; commitment to equity, confidentiality, and participant-centered practice. 

Education and Experience 

• Bachelor’s degree in workforce development, human services, education, business, public administration, or a related field preferred; equivalent relevant experience, specialized training, certifications, and leadership accomplishments will be considered. 

• Minimum eight (8) years of progressive experience in workforce development, career services, job placement, employer engagement, retention, or related community-based programs. 

• At least three (3) years of program or project leadership, including operational coordination, performance accountability, staff or intern coaching, or cross-functional service delivery. 

• Experience in publicly funded or performance-based workforce systems (such as NYC SBS, DYCD, HRA, or comparable programs) and familiarity with reporting and compliance expectations preferred. 

• Professional training or credentials in career or life coaching, project management, workforce services, or related disciplines valued. 

Performance and Accountability 

In collaboration with OBT leadership, establish annual goals that reflect both the Director’s direct alumni job-development caseload and leadership responsibility for alumni retention, re-engagement, events, employer partnerships, verification, data quality, and reporting. Assigned service members and interns support implementation and do not carry the Director’s placement caseload. 

Working Structure 

The position is primarily remote, with occasional on-site events and meetings. The Director retains ownership of strategy, direct career services, communications design, event leadership, retention initiatives, and outcomes. Designated support personnel perform approved administrative and logistics functions. Formal supervision and changes to NYC Service-approved member duties remain subject to sponsoring program and OBT requirements. 

Additional Information 

This description summarizes the general nature and level of the position and is not exhaustive. Responsibilities and performance measures may change with organizational needs and required approvals.