Director of Transportation Operations 

Trumbull, CT 

Full-Time | Reports to Chief, Program Services 

Transform Transportation Operations 

Take the next step in your leadership career with The Kennedy Collective, a mission-driven nonprofit that has empowered people with intellectual and developmental disabilities to live, work, and thrive for over 75 years. 

As Director of Transportation Operations, you'll lead the transformation of transportation services for 200+ riders. You'll own a $500K+ P&L, reduce costs 15% within 12 months, enhance stakeholder communications, and implement technology that eliminates waste. This is strategic operations leadership, not logistics management. 

Why You'll Love Working Here 

• Competitive Compensation: $70,000-$80,000 base salary 

• Performance Incentives: 15% of total compensation tied to measurable outcomes. Target total comp: $80,500-$92,000 in Year 1 

• Comprehensive Benefits: Medical, Dental, Vision, 401(k), and generous Paid Time Off 

• Strategic Leadership: Own P&L, technology decisions, and stakeholder relationships 

• Mission-Driven Work: Your operational excellence directly impacts client service quality and organizational sustainability 

• Measurable Impact: Clear performance metrics tied to financial health, service reliability, and stakeholder satisfaction 

What You'll Do 

1. Supervise driver team with performance scorecards tied to on-time metrics, safety, and client interaction. 

2. Deploy automated communication system for families, external providers, internal TKC managers, and state stakeholders with real-time ETAs, service alerts, and transparent service recovery protocols. 

3. Evaluate, select, and implement integrated route optimization platform, replacing legacy GPS-only tracking within 90 days. 

4. Own transportation P&L ($500K+ budget) and deliver 15% cost reduction by analyzing route efficiency, vehicle utilization, and maintenance costs. 

5. Coordinate vehicle maintenance with procurement manager to minimize downtime and control costs. 

6. Build strategic relationships with CT DDS/DOT officials to secure funding and influence policy (includes but not limited to grant writing, increased ridership and reimbursement negotiations) 

Application Requirements 

Submit resume and application with cover letter (2 pages maximum) addressing the following four questions: 

1. Stakeholder Communication & Crisis Management: Describe a time you had to communicate with multiple stakeholders during a service failure or crisis (families, staff, external partners, leadership). What was the situation, how did you manage communication across all groups, what was your approach to transparency, and what was the outcome? 

2. Operational Excellence & Technological Implementation: Describe a time you implemented technology to improve operational efficiency. What problem were you solving, how did you evaluate options, what were the implementation challenges, and what measurable improvements did you achieve (cost savings, time reduction, error reduction, etc.)? 

3. Financial Leadership: Describe the most significant cost reduction or efficiency initiative you've led. Include baseline costs, your strategy, implementation approach, measurable results, and timeline. 

4. First 90 Days Plan: If you started Monday, what would you do in the first 90 days to (a) understand our cost structure and identify savings opportunities, (b) assess current technology and propose improvements, (c) build credibility and trust with families, staff, external providers, and state agencies? 

About The Kennedy Collective 

For more than 75 years, The Kennedy Collective has been creating opportunities and inclusion for people with intellectual and developmental disabilities across Connecticut. Our team is guided by our values: Challenging the Status Quo, Creating Purpose, Ensuring Inclusion, and Committing to Excellence. 

We are proud to be an Equal Opportunity Employer, welcoming applicants of all backgrounds, abilities, and identities.