Transportation Operations Manager

About the Role You'll keep our Boston fleet moving efficiently and safely every day. Managing a team of drivers and coordinating with dispatch, maintenance, and customer service, you'll optimize routes, respond to real-time disruptions, and maintain the service reliability our customers depend on. From navigating winter weather to managing urban congestion, you'll balance data-driven planning with quick decision-making to hit on-time performance targets while building a culture of safety and accountability. What You'll Do - Oversee daily fleet operations for the Boston metropolitan area, including route assignments, driver scheduling, and real-time coordination to meet on-time delivery commitments - Analyze route performance data and traffic patterns to identify cost-saving opportunities and efficiency improvements, reducing fuel consumption and improving service levels - Manage and develop a team of drivers, conducting performance reviews, providing coaching on safety protocols, and ensuring compliance with DOT hours-of-service regulations - Respond to operational disruptions—weather events, traffic incidents, vehicle breakdowns—by quickly reassigning resources and communicating proactively with customers and internal teams - Maintain rigorous DOT compliance recordkeeping, oversee vehicle inspection programs, and monitor driver hours to ensure full regulatory adherence - Partner with maintenance to prioritize vehicle repairs and plan preventive maintenance schedules that minimize downtime - Generate weekly performance reports using TMS platforms and Excel, tracking KPIs including on-time percentage, cost per mile, and safety incidents What We're Looking For - 3–5 years of transportation or logistics operations experience managing daily fleet coordination, route planning, and driver teams - Strong working knowledge of DOT regulations and compliance requirements with proven ability to maintain accurate hours-of-service records, vehicle inspection logs, and safety documentation - Hands-on experience with Transportation Management Systems (TMS) and GPS fleet tracking platforms—you've used these tools to monitor real-time operations, not just viewed dashboards - Analytical approach to route optimization and cost control, using data (Excel, route optimization software, fleet metrics) to identify efficiency improvements and reduce operational expenses - Proven ability to manage and develop drivers with strong interpersonal skills and a track record of maintaining team morale, safety standards, and on-time performance - Dependable execution under pressure—you've successfully managed time-sensitive logistics through weather disruptions, traffic incidents, and last-minute schedule changes while maintaining service reliability - High attention to detail in operational safety and compliance with systematic approach to pre-trip inspections, maintenance schedules, and regulatory recordkeeping - Valid driver's license and ability to work onsite in Boston, MA Nice to Have - Familiarity with Boston/Northeast operations, including winter weather preparedness, urban congestion management, and regional traffic patterns - Experience with business intelligence or reporting tools (Power BI, Tableau) for operational dashboards and performance analysis - Project management or process improvement experience using methodologies like Lean or Six Sigma