Transportation Director

An Opportunity to Build The South County Connector has grown from an innovative regional initiative into an important public service. Now, Great Barrington is investing in the organization, leadership, systems, employees, partnerships, and customer experience necessary to position that service for the future. The Transportation Director will have the opportunity to help build that future. You will lead a newly established Town department, develop its organizational culture, strengthen regional partnerships, guide operational and financial performance, support and develop employees, and continually improve the experience of the people who rely upon the Connector. This is an opportunity for someone who enjoys building - not simply maintaining. Someone who can see what exists today, imagine what it can become, and bring people together to make that vision real. What You'll Lead As Transportation Director, you will provide strategic leadership for the Town's Transportation Department and the South County Connector. Your work will include: - Building a culture centered on safety, professionalism, accountability, teamwork, innovation, and exceptional customer service. - Leading and developing a team that includes the Operations & Customer Experience Manager, Transportation Administrator, and approximately 20 Transportation Operators. - Developing departmental goals, performance measures, annual work plans, and long-range mobility strategies. - Strengthening the customer experience and continuously improving service reliability, accessibility, and responsiveness. - Building strong relationships with participating municipalities, Councils on Aging, healthcare organizations, employers, schools, nonprofit organizations, disability advocates, and regional partners. - Maintaining a visible presence throughout the South County Connector service area and listening directly to riders and communities. - Managing operating and capital budgets, grants, contracts, procurement, fleet planning, and departmental resources with strong fiscal stewardship. - Using data, employee insight, and customer feedback to make thoughtful decisions and continually improve the service. - Working collaboratively across Town departments so Transportation operates as an integrated municipal service. Minimum Qualifications Candidates should have: - A bachelor's degree in Public Administration, Business Administration, Transportation, Urban Planning, Municipal Management, or a related field. - At least five years of progressively responsible leadership experience in municipal government, transportation, public works, community development, regional planning, or a related public-service organization. - Experience managing personnel, budgets, grants, contracts, and organizational operations. - Demonstrated success building collaborative relationships with governmental agencies, nonprofit organizations, and community stakeholders. - Strong leadership, communication, strategic planning, and organizational management skills. - A valid Driver's License. A master's degree and experience with publicly funded transportation programs, demand-response transportation, regional mobility, Massachusetts municipal finance and procurement, Councils on Aging, healthcare organizations, or regional service providers are preferred.