Senior Director, Workforce Development and Enterprise Operations

Job Type

Full-time

Description

Position Summary

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.

Reporting Structure

The Senior Director reports to the Chief Operating Officer and directly supervises 8 to 10 managers, directors, or functional leaders, each responsible for one or more of the Workforce Development programs or Enterprise Operations business lines named above. The role leads an operation of more than 60 employees across Headquarters, Contract Sites, and Community Work Sites.

The Senior Director works closely with executive leadership, Finance, Human Resources, business development, program leadership, customers, the CT Bureau of Rehabilitation Services, school districts, government agencies, employers, funders, and community partners.

Budget Authority

The Senior Director is accountable for the financial performance of assigned business and service lines within organizational authorization limits. This includes annual operating plans, revenue performance, expense management, budget variance, staffing decisions, purchasing recommendations, contract pricing inputs, resource allocation, and corrective action when financial results do not meet plan.

Essential Duties and Functions

• 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.

Success Measures

Core Expectations

• Provides the Chief Operating Officer with timely, accurate, and decision-ready information.
• Addresses financial, operational, customer, contract, workforce, safety, and compliance concerns promptly.
• Holds managers accountable for commitments, results, documentation, staffing, service quality, and corrective action.
• Makes decisions that balance mission impact, customer requirements, employee needs, financial sustainability, and organizational risk.
• Builds trust through direct communication, reliable follow-through, sound judgment, and consistent leadership practices.

Financial Performance

• Measure: Revenue, operating contribution, expenses, and budget variance for each assigned business or service line.
• Target: Results meet the approved annual operating plan and budget, with documented corrective plans for material unfavorable variances.
• Timeframe: Reviewed monthly and achieved by fiscal year-end.

Contract Performance

• Measure: Contract deliverables, reporting deadlines, service standards, renewals, corrective actions, and compliance findings.
• Target: All material contract requirements and reporting deadlines are met, with no unresolved material compliance finding beyond the approved corrective-action deadline.
• Timeframe: Ongoing, with formal review at least quarterly.

Employment and Workforce Outcomes

• Measure: Performance of Work Services, Project SEARCH, Employment Transition Services, and CT BRS Integrated Employment Services against leadership-approved and funder-required employment, placement, retention, employer-partnership, and service goals.
• Target: Each Workforce Development program meets its approved annual goals and funder requirements and maintains documented action plans for measures that fall below plan.
• Timeframe: Reviewed quarterly and achieved by fiscal year-end.

Customer and Partner Performance

• Measure: Customer commitments, service concerns, issue-resolution status, stakeholder feedback, and relationship health.
• Target: Material customer and partner concerns receive timely acknowledgment, documented ownership, and resolution within contractual or leadership-approved expectations.
• Timeframe: Ongoing, with trends reviewed quarterly.

Cross-Division Execution

• Measure: Completion of approved initiatives involving multiple business lines or departments.
• Target: Assigned strategic and operational initiatives meet their approved scope, owner, milestones, budget, and completion requirements.
• Timeframe: Assessed quarterly against approved project plans.

Leadership and Organizational Capacity

• Measure: Management accountability, succession coverage, performance documentation, staff development, and critical leadership vacancies.
• Target: Every direct report has current goals, documented performance expectations, and an active development or succession plan consistent with organizational practices.
• Timeframe: Established within the first 90 days and reviewed at least quarterly.

General Responsibilities

• 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.

Competencies

Core

• Financial and Commercial Leadership: Connects revenue, expenses, staffing, pricing, contract requirements, and operating decisions to sustainable results.
• Contract and Operational Accountability: Sets clear standards, ownership, controls, and follow-through across varied contracts and business operations.
• Leadership Through Managers: Sets expectations, develops leaders, addresses performance directly, and builds accountable teams across multiple functions.
• Strategic Partnership Development: Builds productive relationships with customers, employers, government agencies, funders, and community partners.

Additional

• Change Leadership: Brings separate programs and business lines under common performance standards and keeps managers accountable through the transition.
• Employment-Centered Decision Making: Weighs every business decision by its effect on jobs for people with disabilities and people facing barriers to employment.

Requirements

Qualifications

Required

• 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.

Preferred

• 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.

Physical Requirements

• Regularly operates a computer and uses a keyboard, screen, telephone, and other standard office equipment.
• Regularly sits for extended periods and periodically stands or walks during meetings and site visits.
• Frequently walks through offices, fitness facilities, warehouse and assembly environments, gallery and exhibition spaces, contract locations, employer and host-business sites, schools, and community-based settings.
• Occasionally bends, reaches, crouches, climbs stairs, and navigates uneven, restricted, active, or outdoor work areas during operational reviews.
• Occasionally lifts, carries, pushes, or pulls materials weighing up to 20 pounds.
• Regularly drives between work locations and may spend extended periods in a vehicle.
• Must be able to communicate effectively in person, by telephone, through virtual platforms, and in writing.
• Must be able to observe operations, review documents and electronic information, identify safety or service concerns, and respond to conditions at varied work locations.
• Must be able to perform the essential functions of the position with or without reasonable accommodation.

Working Conditions

• Works across professional office, fitness, warehouse, assembly, gallery and exhibition, customer, government, employer, school, and community-based environments, with regular travel between organizational locations.
• May encounter noise, moving equipment, cleaning or operational materials, outdoor weather, temperature changes, vehicle traffic, and other conditions associated with active Enterprise Operations and community locations.
• Regularly interacts with executives, directors, managers, employees, program participants, families, customers, employers, school districts, government agencies, f