Chief Transportation Officer

Greater Portland Metro; Portland (ME); On-site; USD 150,000 - 210,000; Full time

Job summary

Greater Portland Metro is seeking a Chief Transportation Officer to lead Operations and Maintenance, oversee safety-sensitive functions, and drive performance across the regional transit system. Reporting to the Executive Director, you will shape strategy, manage budgets, contracts, and capital programs, and represent Metro with partners, riders, and regulators.

The CTO will champion innovation, implement ITS solutions, build strong labor relations, promote employee development, and translate

Qualifications

• 10 years of progressively responsible experience in transit operations and/or transit fleet maintenance.
• 5 years of supervisory/management level experience in transit operations and at least 5 years of supervisory experience in a working environment governed by a collective bargaining agreement.

Responsibilities

• Lead Operations and Maintenance: provide leadership, direction, and oversight to ops and maintenance, staffing, scheduling, fleet management, and service delivery.
• Drive Safe, Service, and Performance: establish metrics and action plans to improve reliability, productivity, safety, and customer experience.
• Lead People and Culture: foster a positive, accountable, collaborative work environment and manage performance with respect to collective bargaining.
• Manage Labor Relations: maintain productive relationships with union reps and participate in contract negotiations and grievances.
• Ensure Regulatory Compliance: oversee compliance with local, state, and federal requirements, including FTA regulations.
• Manage Resources and Budget: contribute to annual operating budgets and five-year capital programs; optimize resources.
• Oversee Fleet and Infrastructure: manage bus fleet, facilities, and infrastructure.
• Lead Technology and Innovation: plan and manage ITS and technology applications to improve service.
• Manage Projects and Contracts: provide technical expertise and manage transportation initiatives with consultants and vendors.
• Oversee Fare Administration: work with fare vendors and reporting for partner agencies.
• Build Partnerships and Represent Metro: collaborate with internal departments and external stakeholders; represent Metro professionally.

Skills

Operational leadership

Public transportation

Fleet management

Labor relations

Budgeting & financials

Stakeholder engagement

Data-driven decision making

Strategic planning

Safety leadership

Tools

ITS

Job description

Lead the Future of Public Transportation in Greater Portland

Greater Portland Metro is seeking an experienced and collaborative Chief Transportation Officer (CTO) to lead its Operations and Maintenance divisions and help shape the future of public transportation across the Greater Portland region.

This is a high-impact leadership opportunity for a transportation professional who is energized by complex operations, engaged leadership, innovation, and the opportunity to make a meaningful difference in the communities Metro serves.

Reporting directly to the Executive Director, the CTO provides strategic and operational leadership for Metro's transportation and maintenance functions, with responsibility for delivering transit service that is safe, reliable, professional, productive, and cost-effective. The CTO oversees a large safety-sensitive operation and works closely with employees, union representatives, senior leadership, community partners, government agencies, Board of Directors, transit users, and other stakeholders.

The ideal candidate is a visible and approachable leader who can balance the demands of daily transit operations with long-term strategic planning. They will bring strong operational judgement, a commitment to employee engagement, a collaborative leadership style, and the ability to turn data and performance measures into meaningful improvements.

The Opportunity

The Chief Transportation Officer will have the opportunity to:

• Lead Metro's Operations and Maintenance divisions and directly influence the quality, reliability, and efficiency or regional transit service.
• Lead and develop employees while strengthening a culture of safety, accountability, collaboration, and positivity.
• Evaluate and improve transit operations through performance metrics, staffing analysis, scheduling, route and service evaluation, and operational planning.
• Work collaboratively with ATU Local 714 and other stakeholders to maintain productive labor-management relationships and address collective bargaining and employee relations matters.
• Help guide Metro's long-term fleet, infrastructure, technology, and capital investment strategies.
• Champion innovation and implement technology and intelligent transportation systems that improve service and operational performance.
• Participate in annual operating budget development and the five-year Capital Improvement Program, helping ensure resources are aligned with Metro's strategic priorities.
• Manage major transportation projects involving internal teams, consultants, contractors, vendors, and partner organizations.
• Represent Metro with community leaders, member agencies, stakeholder organizations, transit riders, the media, and the broader transportation industry.
• Work closely with the Executive Director, Board of Directors, and senior leadership team on strategic initiatives that affect Metro's future.

Requirements

• 10 years of progressively responsible experience in the fields or transit operations and/or transit fleet maintenance.
• 5 years of supervisory/management level experience in transit operations and at least 5 years of supervisory experience in a working environment governed by a collective bargaining agreement.

Key Responsibilities

Lead Operations and Maintenance

Provide leadership, direction, and oversight to Operations and Maintenance, ensuring effective staffing, scheduling, training, fleet management, service delivery, facility maintenance, and daily transportation operations.

Drive Safe, Service, and Performance

Establish and monitor performance metrics and action plans to improve service reliability, productivity, safety, efficiency, and customer experience. Evaluate routes, schedules, staffing levels, overtime, and operational practices to meet changing market and community needs.

Lead People and Culture

Foster a positive, accountable, and collaborative work environment. Maintain accessibility to employees, strengthen morale and engagement, and ensure employees are properly trained and supported. Manage performance, hiring, discipline, and other personnel matters in accordance with Metro policies, collective bargaining agreements, and applicable laws.

Manage Labor Relations

Maintain effective working relationships with union representatives and ensure compliance with applicable collective bargaining agreements. Investigate work-rule and CBA violations, resolve first-step grievances, and participate in contract negotiations, grievance resolution, arbitrations, and other labor matters in collaboration with Human Resources, the Executive Director, and legal counsel.

Ensure Regulatory Compliance

Oversee Operations and Maintenance activities to ensure compliance with applicable local, state, and federal requirements, including Federal Transit Administration regulations. Develop, implement, and regularly update policies, procedures, and business practices that support regulatory compliance.

Manage Resources and Budget

Participate in development of Metro's annual operating budget and five-year Capital Improvement Program. Develop recommendations that improve service and operational performance while supporting long-term fiscal sustainability. Manage approved budgets and assigned capital projects.

Oversee Fleet and Infrastructure

Manage, maintain, and optimize Metro's bus fleet, support vehicles, buildings, bus stops, transit centers, fueling facilities, and other transportation infrastructure.

Lead Technology and Innovation

Champion innovation and identify creative solutions to improve transit performance and operational efficiency. Plan, implement, and manage intelligent transportation systems (ITS), technology applications, and other tools designed to improve service delivery and decision-making.

Manage Projects and Contracts

Provide technical expertise and serve as project manager for transportation initiatives involving professional staff, consultants, contractors, and external partners. Assist with the development, administration, and evaluation of contracts supporting Operations and Maintenance.

Oversee Fare Administration

Serve as Metro's fare administrator and work directly with the fare collection vendor to ensure fares are administered in accordance with Metro's approved fare structure. Support partner transit agencies with fare collection reporting and administrative activities as needed.

Build Partnerships and Represent Metro

Work collaboratively with internal departments, member communities, partner transit agencies, government agencies, stakeholders, and other organizations to develop an integrated and effective regional transit system. Represent Metro professionally with the Board of Directors, community organizations, transit users, media, and the transportation industry.

Provide complex operational, administrative, and strategic assistance to the Executive Director and other members of Metro's management team.

What You'll Bring

Metro is looking for a leader who combines operational expertise with strong people leadership. The successful candidate will demonstrate:

• Significant leadership experience in public transportation, transit operations, fleet management, maintenance, or a closely related transportation environment.
• Experience leading complex, multi-functional operations, preferably in a unionized or similarly structured organization.
• A demonstrated ability to build trust, communicate effectively, and work collaboratively with employees at all levels.
• Strong knowledge of transportation operations, maintenance practices, scheduling, staffing, performance management, and operational planning.
• Experience working with collective bargaining agreements and resolving employee and labor relations issues.
• The ability to interpret and apply federal, state, and local regulations in a safety-sensitive operating environment.
• Strong financial and organizational skills, including experience with budgets, capital planning, contracts, and resource allocation.
• The ability to analyze performance data and use measurable results to identify opportunities and drive improvement.
• Strong written and verbal communication skills, including the ability to explain complex issues clearly to elected or appointed officials, employees, stakeholders, the media, and the public.
• A commitment to safety, customer service, employee development, innovation, and continuous improvement.
• The judgment, integrity, and professionalism required to represent Metro effectively in a highly visible leadership role.

Why Join Metro?

Metro is more than a transportation provider. Our work connects people to jobs, education, healthcare, businesses, services, and one another across Southern Maine.

As Chief Transportation Officer, you will have the opportunity to influence how public transportation operates today while helping plan for the system Metro will need tomorrow. You will work alongside dedicated transportation professionals and have a direct role in improving service, developing employees, managing resources, and advancing Metro's mission.

Metro's values of Safety, Service, Simplicity, Sustainability, and Innovation guide how we approach our work and our responsibility to the communities we serve.

If you are a transportation leader who enjoys solving complex problems, developing people, improving operations, and working collaboratively to deliver results, Metro invites you to bring your experience and leadership to this important role.

Our Mission

To provide a public transportation experience that is frequent, fast, safe, and simple.