Transportation Director

Advancing the Town of Great Barrington's mission by creating a transportation system that people trust, value, and can confidently rely upon every day through exceptional public service and thoughtful stewardship of public resources, the Transportation Director ensures that every person who depends on the South County Connector has access to safe, reliable, accessible, and welcoming transportation that strengthens independence, connects communities, and enhances quality of life.

About the role

The Director leads the South County Connector as a community-centered transportation service where every interaction reflects the Town's commitment to professionalism, respect, safety, and service excellence. Recognizing that transportation is more than moving people from one place to another, the Director fosters an organizational culture that values dignity, responsiveness, and meaningful connections while ensuring riders have dependable access to healthcare, employment, education, shopping, recreation, municipal services, and other essential destinations.

Serving as the Town's regional mobility leader, the Director maintains an active presence throughout the South County Connector service area and builds strong partnerships with participating municipalities, Councils on Aging, healthcare providers, employers, educational institutions, community organizations, and regional agencies. Through collaboration, innovation, and community engagement, the Director continually seeks opportunities to strengthen mobility, remove barriers to transportation, and improve the customer experience while ensuring services remain financially responsible, operationally effective, and responsive to evolving community needs.

The Director provides strategic leadership for the Transportation Department by establishing a culture of integrity, accountability, teamwork, innovation, and continuous improvement. Every decision is guided by the Department's commitment to delivering exceptional transportation experiences, exercising responsible stewardship of public resources, and maintaining the public's trust through dependable service, fiscal responsibility, and operational excellence.

Supervision

Reports To: Town Manager

• Directly supervises the Operations & Customer Experience Manager, and the Transportation Administrator.
• Indirectly supervises the Transportation Operators (approximately 20 staff).

Responsibilities

Leadership & Strategic Management

• Provide executive leadership for the Transportation Department consistent with the Town's mission, values, and strategic priorities.
• Develop departmental goals, annual work plans, performance measures, and long-range mobility strategies.
• Promote a culture centered on safety, professionalism, accountability, innovation, collaboration, and exceptional customer service.
• Lead continuous improvement initiatives that enhance service quality, operational effectiveness, and customer satisfaction.
• Ensure departmental resources are aligned with the Town's priorities and used efficiently and responsibly.
• Foster a collaborative culture by building strong working relationships with Finance, Human Resources, Public Works, Information Technology, and other Town departments to ensure the Transportation Department operates as an integrated municipal service.

Community Leadership & Partnerships

• Serve as the Town's primary representative for regional transportation and mobility initiatives.
• Maintain regular communication and working relationships with each participating Council on Aging to understand community transportation needs, improve service accessibility, and strengthen partnerships.
• Meet routinely with municipal leaders, healthcare providers, employers, schools, nonprofit organizations, disability advocates, and community groups to identify opportunities to improve mobility for existing riders and communities.
• Maintain a visible presence throughout the South County Connector service area by participating in community meetings, outreach events, and rider engagement activities.
• Promote public awareness of transportation services and encourage community participation in service improvement initiatives.

Operational Excellence

• Ensure the South County Connector consistently delivers safe, reliable, accessible, and customer-focused transportation services throughout the existing service area.
• Monitor operational performance, customer satisfaction, ridership trends, and financial performance to support informed decision-making.
• Evaluate operations regularly to identify efficiencies, improve customer experience, and strengthen service reliability.
• Ensure service levels remain responsive to community needs while maintaining responsible stewardship of Town resources.
• Work collaboratively with the Operations & Customer Experience Manager to maintain high standards of service delivery and employee performance.

Fiscal Stewardship

• Promote a culture of fiscal accountability throughout the Transportation Department by ensuring that budgets, payroll, procurement, grants, and financial records are accurate, timely, transparent, and fully compliant with Town policies and applicable laws.
• Develop and administer the department's annual operating and capital budgets.
• Pursue grant opportunities and other funding sources that support the Town's transportation objectives while maintaining long-term financial sustainability.
• Oversee contracts, procurement activities, and vendor relationships in accordance with applicable laws and Town policies.
• Ensure responsible management of departmental assets, equipment, and financial resources.
• Collaborate with the Department of Public Works on long-range fleet replacement planning, capital equipment needs, and vehicle lifecycle strategies to support the Transportation Department's operational and financial objectives.
• Provide regular reports to the Town Manager regarding departmental performance, budget status, and strategic initiatives.

Personnel Leadership

• Recruit, develop, mentor, and evaluate departmental staff.
• Foster an organizational culture built on teamwork, accountability, communication, respect, and continuous learning.
• Support succession planning, cross-training, and employee development.
• Promote employee engagement and recognize outstanding performance.

Compliance & Risk Management

• Ensure compliance with all applicable federal, state, and local laws, regulations, grant requirements, and Town policies.
• Oversee departmental safety initiatives, emergency preparedness, and risk management programs.
• Ensure accurate reporting, documentation, and regulatory compliance.

Continuous Improvement

• Utilize operational data, customer feedback, and employee input to improve service quality and organizational effectiveness.
• Evaluate emerging technologies and best practices that improve operational efficiency and customer experience.
• Recommend service enhancements only when they strengthen existing services, align with Town priorities, are financially sustainable, and do not diminish the quality or reliability of service provided to current communities.

Requirements

Minimum Qualifications

• Bachelor's degree in Public Administration, Business Administration, Transportation, Urban Planning, Municipal Management, or a related field.
• Five (5) years of progressively responsible leadership experience in municipal government, transportation, public works, community development, regional planning, or a related public service organization.
• Demonstrated experience managing personnel, budgets, grants, contracts, and organizational operations.
• Experience building collaborative partnerships with governmental agencies, nonprofit organizations, and community stakeholders.
• Excellent leadership, communication, strategic planning, and organizational management skills.
• Valid Driver's License.

Preferred Qualifications

• Master's degree in Public Administration, Business Administration, Transportation Planning, or a related field.
• Experience administering state or federally funded transportation programs.
• Experience working with demand-response transportation or regional mobility services.
• Knowledge of Massachusetts municipal finance, procurement, and applicable Massachusetts General Laws.
• Experience collaborating with Councils on Aging, healthcare organizations, and regional service providers.

Work Environment and Physical Requirements

• Work is performed in office, field, and community settings and requires frequent travel throughout the South County Connector service area.
• Regular attendance at meetings with municipal officials, Councils on Aging, healthcare providers, community organizations, and regional partners.
• Frequent visits to transportation operations, vehicles, and service locations.
• Attendance at occasional evening meetings, community events, and emergency response activities as operational needs require.
• Ability to respond to operational emergencies outside normal business hours.
• Ability to sit, stand, and walk for extended periods.
• Ability to travel throughout the South County Connector service area.
• Ability to inspect vehicles and transportation facilities.
• Ability to lift and carry up to 25 pounds.
• Ability to operate standard office equipment, computers, and mobile communication devices.
• Ability to communicate effectively in person, by telephone, and in public settings.
• Ability to safely operate a motor vehicle.