Senior Director, Workforce Development and Enterprise Operations

The Kennedy Collective • Trumbull, CT

2d • Hybrid

About The Position

The Senior Director, Workforce Development and Enterprise Operations leads Workforce Development (Work Services, Project SEARCH, Employment Transition Services, and CT BRS Integrated Employment Services) and Enterprise Operations (the Autism Health & Fitness Center, warehouse and assembly, HUD operations, Mobility Services, and the Maggie Daly Arts Cooperative Gallery and exhibitions). The role owns financial performance, contract outcomes, service quality, growth, employment results, and manager development across those programs and business lines. The Senior Director turns organizational strategy into operating plans and holds assigned leaders accountable for measurable financial, operational, employment, customer, and compliance outcomes.

Requirements

• Demonstrated experience leading multiple business, employment, contract, or community-based service operations.
• Demonstrated responsibility for revenue, expenses, budgets, forecasting, financial performance, and corrective action.
• Experience managing managers, supervisors, or functional leaders across multiple operations or locations.
• Contract-management experience involving government, commercial, community, or partnership agreements.
• Experience setting and monitoring operational, financial, customer, workforce, safety, and compliance performance measures.
• Ability to satisfy applicable background screening, customer-site, government-facility, and badging requirements.
• Advanced ability to use Microsoft 365 and financial, operational, contract, workforce, or customer-management systems.
• Valid driver's license and ability to travel regularly between organizational, customer, government, employer, partner, and community locations.
• Ability to work a flexible full-time schedule, including evenings and weekends when operational, customer, contract, or organizational needs require.

Nice To Haves

• Experience leading social enterprise, employment-services, workforce-development, fitness, warehouse, assembly, mobility, HUD, arts and exhibitions, or other revenue-generating operations.
• Experience with government contracting, regulated service environments, contract renewals, proposals, pricing, or business development.
• Experience connecting business operations with employment opportunities for people with disabilities or people facing barriers to employment.
• Experience with CT Bureau of Rehabilitation Services (BRS) programs, Project SEARCH, or school-to-work transition services.
• Experience developing employer, customer, government, and community partnerships.
• Experience leading organizational change or bringing separate programs and business lines under common performance standards.

Responsibilities

• Own financial performance across Workforce Development programs and Enterprise Operations (the Autism Health & Fitness Center, warehouse and assembly, HUD operations, Mobility Services, and the Maggie Daly Arts Cooperative Gallery and exhibitions), including top-line revenue growth, bottom-line profitability, forecasting, expense control, authority to make staffing decisions, and corrective action.
• Lead contract performance and administration across government, state agency (including CT BRS), school district, commercial, community, and partnership agreements by setting clear ownership for deliverables, reporting, renewals, customer commitments, documentation, compliance, and issue resolution.
• Drive growth and business development by identifying and advancing new contracts, employer relationships, customer opportunities, strategic partnerships, referral channels, pricing, and mission-based revenue opportunities.
• Build consistent operating standards for staffing, service delivery, customer responsiveness, quality, safety, documentation, data integrity, contract execution, and management accountability across distinct business and service lines.
• Lead Work Services, Project SEARCH, Employment Transition Services, and CT BRS Integrated Employment Services so more people with disabilities and people facing barriers to employment get, keep, and advance in meaningful jobs, connecting those programs with Enterprise Operations and employer partners.
• Hold direct reports accountable for performance, staffing, service quality, safety, and follow-through.
• Maintain accurate, timely, decision-ready financial, contract, workforce, and operational information.
• Communicate material risks, missed commitments, compliance concerns, and corrective actions promptly to the Chief Operating Officer.
• Maintain a consistent compliance posture across responsibility levels and assigned business operations.
• Strengthen cross-division execution by coordinating shared priorities, resources, customer relationships, transportation access, employment supports, and operational decisions across Workforce Development, Social Enterprises, Mobility Services, and supporting administrative departments.
• Support and uphold The Kennedy Collective's mission, values, policies, procedures, and standards of professional conduct.
• Promote a respectful, person-centered environment that supports the dignity, rights, choice, independence, and well-being of the individuals we serve.
• Maintain professional, respectful, and collaborative relationships with individuals served, families, coworkers, supervisors, other departments and programs, community partners, customers, and other stakeholders, and contribute to a positive, solutions-focused workplace.
• Comply with all applicable federal and state laws, regulatory requirements, contractual obligations, accreditation standards, and organizational policies, and maintain confidentiality of sensitive personal, health, employee, and organizational information.
• Complete required orientation, training, certifications, and professional development within established timeframes, maintain required credentials, and participate in meetings, organizational initiatives, and quality-improvement activities.
• Follow established health, safety, emergency, incident-reporting, and risk-management practices, and promptly communicate concerns, incidents, compliance issues, and safety risks through appropriate channels.
• Maintain accurate, timely, and complete records, documentation, timekeeping, and other required information applicable to the position.
• Demonstrate reliability and accountability by maintaining regular attendance, punctuality, and availability consistent with the requirements of the position.
• Use organizational resources, equipment, technology, systems, and property responsibly and in accordance with established policies.
• Provide support and coverage across programs, locations, shifts, and service settings as assigned, including residential, day, community-based, and other agency programs regardless of primary work assignment, and perform other duties reasonably related to the position based on organizational or operational needs.

Benefits

• Medical, dental, and vision insurance
• Health Savings Account (HSA) and Flexible Spending Account (FSA) options, where applicable
• Employer-paid life and disability insurance
• Retirement savings plan with employer contributions, if eligible
• Paid time off (Vacation and Sick Time including floating holidays)
• Employee Assistance Program (EAP)
• Professional development and training opportunities
• Employee discount and wellness programs
• Additional voluntary benefits offered by The Kennedy Collective

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed