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Transit Operations Team Leader; PM

Job in Great Barrington, Berkshire County, Massachusetts, 01230, USA
Listing for: Town of Great Barrington
Full Time position
Listed on 2026-02-15
Job specializations:
  • Management
    General Management
  • Transportation
Salary/Wage Range or Industry Benchmark: 53000 USD Yearly USD 53000.00 YEAR
Job Description & How to Apply Below
Position: Transit Operations Team Leader (PM)

Salary Range:
Starting at $53,000 annually

Schedule:

Wednesday–Saturday, approximately 11:00 a.m. – 9:15 p.m.

A $2,000 Vehicle Maintenance Coordinator annual stipend is additionally available to the right candidate, depending on experience

Position Summary

The Operations Team Leader (PM) functions as an assistant manager for daily transit operations of the South County Connector. This position provides leadership during assigned PM shifts, ensures safe and reliable service delivery, and supports the Transit Operations Manager in staff supervision, operational planning, and performance management. The Operations Team Leader exercises independent judgment in day-to-day operational decision-making and serves as the management representative during assigned coverage periods.

The Operations Team Leader leads from both the field and the office. This role regularly operates revenue service vehicles to maintain service continuity, model best practices, and provide real-time coaching and oversight of Transit Team Members. The position also provides dispatch coverage as part of assigned duties, spending approximately 40% of the workweek in the operations office coordinating service and supporting field staff.

There are three (3) Operations Team Leaders who collectively oversee all Transit Team Members. Each Operations Team Leader is responsible for supervising approximately one-third of the Transit Team Member staff, aligned with their regular shift assignments.

Essential Duties and Responsibilities Operational Leadership
  • Oversee daily service delivery during assigned PM shifts through a combination of field presence, vehicle operation, and dispatch oversight to ensure safe, efficient, and reliable transit operations.
  • Serve as the primary operational decision-maker during scheduled coverage, including afternoons, evenings, weekends, and after-hours as assigned.
  • Lead responses to service disruptions, incidents, and emergencies; determine corrective actions and escalation needs.
  • Monitor on‑time performance, service quality, and rider experience; implement real‑time operational adjustments as needed.
Field & Dispatch Leadership
  • Regularly operate transit vehicles to support service delivery, respond to staffing gaps, and maintain operational continuity.
  • Lead from the field by modeling safe driving practices, customer service standards, and regulatory compliance.
  • Provide real‑time coaching, guidance, and support to Transit Team Members while in service.
  • Provide dispatch coverage for approximately 40% of the workweek, coordinating vehicle assignments, monitoring service conditions, and supporting drivers in real time.
  • Maintain situational awareness across both field and dispatch operations to ensure effective communication and timely decision-making.
Staff Supervision & Development
  • Provide direct supervision to approximately 5–8 Transit Team Members aligned with assigned shifts.
  • Serve as the primary supervisor for assigned staff, including coaching, performance feedback, and corrective action in coordination with the Transit Operations Manager.
  • Assist with recruitment, onboarding, training, and mentoring of Transit Team Members.
  • Promote a culture of safety, accountability, teamwork, and customer service.
Administrative & Compliance Responsibilities
  • Ensure compliance with Town policies and applicable FTA, MassDOT, and safety regulations.
  • Review and approve operational documentation, including incident reports, dispatch logs, vehicle inspections, and time‑keeping records.
  • Assist with scheduling, coverage coordination, and leave management for assigned staff.
  • Support audits, reporting, and data collection related to operations, safety, and service performance.
Leadership & Strategic Support
  • Partner with the Transit Operations Manager on operational planning, service improvements, and policy implementation.
  • Identify trends, risks, and opportunities for increased efficiency or improved service delivery.
  • Serve as a liaison between Transit Team Members and department leadership, communicating operational needs and recommendations.
  • Act as the Transit Operations Manager’s designee during assigned shifts or when directed.
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