Vice President of Workforce & Operations

The Kennedy Collective • Trumbull, CT

21h • Hybrid

About The Position

The Vice President of Workforce and Operations provides strategic leadership and operational oversight for Workforce Development, Social Enterprises, and Mobility Services. Under the leadership of the Chief Operating Officer (COO), this position provides direct supervision, coaching, and development to a team of directors and managers while leading operational and financial performance across multiple service lines, locations, government contracts, and mission-aligned enterprise operations. The Assistant Vice President oversees P&L performance, business development, government contracting, workforce initiatives, service delivery, and operational strategy; develops organizational capability and scalable business practices; and drives sustainable growth through strong financial management, strategic partnerships, and continuous improvement. This position balances financial discipline with human-centered service delivery to ensure operations align with organizational objectives, regulatory requirements, and The Kennedy Collective's mission, vision, and values.

Requirements

• Bachelor's degree in Business Administration, Operations Management, Human Services, Workforce Development, or a related field required; equivalent relevant experience may be considered.
• Minimum of seven (7) years of progressively responsible leadership experience within a complex, multi-site organization.
• Demonstrated experience with P&L ownership, revenue growth, budgeting, forecasting, variance analysis, and financial decision-making.
• Experience overseeing operations generating $5 million or more in annual revenue through government contracts, enterprise operations, or service delivery.
• Experience leading and developing directors and managers, including coaching, performance management, and succession planning.
• Experience managing federal, state, or municipal contracts and related regulatory, labor, and reporting requirements.
• Demonstrated success building relationships with government agencies, customers, funders, and community partners.
• Valid driver's license and ability to travel between TKC locations as needed.

Nice To Haves

• Master's degree or MBA in Business Administration, Operations Management, Human Services, Workforce Development, or a related field.
• Experience within nonprofit human services, workforce development, disability services, or social enterprise operations.
• Experience managing federal or government-funded contracts, including GSA, T2E, DMHAS, or similar programs.
• Knowledge of Service Contract Labor Standards (SCLS/SCA), prevailing wage requirements, federal procurement, and government contracting.
• Experience leading business development, service expansion, or other revenue-generating initiatives.
• Project management, continuous improvement, or operational excellence experience preferred.

Responsibilities

• Provide strategic leadership, operational oversight, coaching, and performance management across Workforce Development, Social Enterprises, and Mobility Services while fostering accountability, collaboration, innovation, and continuous improvement.
• Lead and develop directors and managers across assigned divisions, establishing clear performance expectations, strengthening leadership capability, and building organizational bench strength.
• Oversee day-to-day operations across multiple programs, contracts, and locations, proactively addressing operational barriers, staffing and coverage needs, customer escalations, facilities disruptions, and other business-critical issues.
• Establish and facilitate regular operating and business reviews focused on key performance indicators (KPIs), financial performance, service outcomes, corrective actions, and continuous improvement.
• Collaborate with the Chief Operating Officer and organizational leadership to translate strategic priorities into departmental goals, scorecards, staffing models, and measurable performance expectations.
• Own and drive P&L performance across assigned divisions, ensuring revenue growth, financial sustainability, operational efficiency, and achievement of contractual and organizational performance expectations.
• Develop and sustain revenue streams through federal contracts, state-funded programs, commercial customers, and mission-aligned business opportunities.
• Identify opportunities for expansion, new business development, service diversification, and increased organizational capacity; develop business cases, resource plans, and implementation strategies to support sustainable growth.
• Collaborate with the Chief Financial Officer, Chief Operating Officer, and organizational leadership on budgeting, forecasting, financial planning, variance management, and resource allocation.
• Cultivate relationships with government agencies, funding sources, customers, employers, and community partners to strengthen existing business and identify new opportunities.
• Represent The Kennedy Collective externally to strengthen organizational visibility, develop strategic partnerships, and position the organization for continued growth and sustainability.
• Provide executive oversight of workforce development programs, social enterprise operations, and mobility services to ensure high-quality service delivery, achievement of performance outcomes, and fulfillment of contractual requirements.
• Partner with workforce development leaders and employment teams to strengthen referral, assessment, job development, placement, and retention processes.
• Implement strategies and systems that increase competitive integrated employment outcomes, including placement, retention, wages, hours worked, and other established performance indicators.
• Provide strategic direction for employer development, employer relationship management, customized employment strategies, and other approaches that expand employment opportunities for individuals served.
• Advance career pathway, training-to-employment, and workforce development models aligned with participant goals, employer needs, and labor market demand.
• Drive execution of strategic initiatives that strengthen and expand Social Enterprises, Workforce Development, and Mobility Services while maintaining service quality and mission alignment.
• Ensure assigned divisions operate in compliance with federal, state, and local laws and regulations, contractual requirements, funding requirements, labor standards, organizational policies, and applicable quality standards.
• Maintain working knowledge of government contracting requirements, employment regulations, labor standards, and other regulatory requirements impacting assigned divisions.
• Ensure accurate and timely documentation, reporting, and data management across workforce development, enterprise, mobility, and contract-related systems.
• Develop and monitor operational metrics, dashboards, financial reports, and performance data to support executive decision-making and continuous improvement.
• Identify operational, financial, contractual, and compliance risks and implement timely corrective actions, escalating significant concerns to executive leadership as appropriate.
• Maintain appropriate responsiveness to operational emergencies, contract-critical matters, executive leadership, direct reports, customers, and external partners.
• Demonstrate professionalism, integrity, ethical leadership, accountability, sound judgment, and effective stewardship of organizational resources.
• Build collaborative relationships with executives, organizational leaders, employees, government agencies, customers, employers, funding sources, and community partners.
• Develop talent through structured supervision, coaching, performance management, succession planning, and professional development while building the next generation of The Kennedy Collective leaders.
• Lead organizational and operational change initiatives that improve service delivery, financial performance, organizational capacity, and overall effectiveness.
• Model The Kennedy Collective's Core Values in interactions with employees, customers, partners, and the individuals served.
• Maintain knowledge of emerging trends, regulations, funding opportunities, government contracting requirements, workforce development practices, and operational best practices relevant to assigned divisions.
• Perform other duties, assignments, and strategic initiatives as assigned in support of operational and organizational objectives.

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 and 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: Executive