Fleet Manager Jobs in Roxbury, MA (NOW HIRING)

The Landline Company (landlineco.com) is revolutionizing air travel by bridging the gap between regional communities and major airline hubs. We partner with top airlines like American and Air Canada to offer innovative multimodal connections across North America. We’ve launched a first of its kind remote terminal checkpoint to expand the reach of major metro airports into local neighborhoods . Our luxury motorcoaches replace short flights with a faster, more sustainable alternative in reducing costs, addressing pilot shortages, and enhancing passenger journeys.  

Salary: 90,000 – 120,000

Job Type: Full Time, Salary Exempt

The Role: 
The Fleet Manager oversees Landline’s fleet management and maintenance functions. The role ensures the fleet is safe, clean, compliant, available, and maintained in accordance with OEM maintenance intervals, regulatory and Landline operational requirements. The Fleet Manager is the single point of contact for the Landline leadership team, maintenance business partners, OEMs, and our dispatch team.

The role will lead the maintenance function within Operations. This includes 2-4 direct reports, both salaried (fleet manager) and hourly (in-house mechanics) which may expand over time

What You’ll Do:

• Own the maintenance function at Landline with the plan, vendors and data for our fleet, with a path to scaling to support a 100-motorcoach fleet in the future
• Build and maintain a rolling maintenance forecast aligned to OEM intervals and usage patterns, keeping every vehicle within OEM PM intervals
• Maintain the maintenance budget with Finance, including updates and variance reporting
• Coordinate unscheduled and corrective maintenance without disrupting service operations
• Keep accurate service records in Fleetio and Samsara; track DVIR resolution and escalate out-of-service conditions to System Operations Control (SOC - Dispatch)
• Manage parts and consumables procurement and validate pass-through costs from our maintenance partners
• Flag recurring issues or vehicles approaching end of useful life using maintenance data
• Serve as Landline's representative for all work at external maintenance facilities; issue work orders to fully utilize dedicated resources
• Schedule all planned and unplanned work and ensure buses are positioned on time
• Review and approve partner invoices, flag discrepancies, and track overflow technician usage against budget
• Plan and conduct quarterly reviews with key maintenance vendors
• Give the SOC and leadership a real-time view of fleet readiness (operational, in maintenance, or out of service) and communicate constraints proactively
• Own Fleetio and Samsara as key user, including partner access and IT interfaces
• Plan and manage vehicle assignments, identify capacity risks in advance, and support planning for additions, retirements, and configuration
• Maintain vehicle files (registration, insurance, inspections, warranties)
• Serve as primary contact with OEM reps; manage warranty claims and authorizations and coordinate technician training
• Track Technical Service Bulletins (TSBs), service bulletins, and recalls and ensure timely action; advise leadership on OEM reliability and procurement
• Provide the SOC advance notice of maintenance windows, report unplanned outages with return-to-service estimates, and collaborate on scheduling trade-offs
• Ensure federal, state, and local compliance and timely inspections; keep audit-ready records and report KPIs (MTBF, out-of-service days, cost per vehicle)
  

What We’re Looking For: 

• 5-10 years of experience in transportation operations, logistics, aviation, fleet operations, or operations-focused consulting including transportations, or a similar field
• A degree in Industrial Engineering, Operations Research, Supply Chain, a related field or equivalent hands-on experience in a transportation logistics and/or operations environment
• Strong data and analytical skills (Excel required; SQL, Python, or BI tools like Tableau/Power BI a plus)
• Comfort using and recommending AI tools (e.g. Claude Code or similar) to move quickly across a diverse and shifting set of projects
• Excellent communication and interpersonal skills with the ability to work with frontline hourly staff
• A high-energy, self-directed approach and enthusiasm for solving operational problems in a fast-moving startup environment
• Familiarity with Fleetio, Samsara, or similar fleet-management/telematics platforms is a strong plus
• Comfort working remotely while collaborating across multiple locations and time zones
• The ability to think "bigger" than any single function as someone who understands the balancing act between commercial, finance, and operations, and can design solutions that serve the whole business rather than optimizing for one group at another's expense
• Six Sigma certification (Green Belt, Black Belt, etc.) is a nice-to-have
• Comfort working remotely while collaborating across multiple locations and time zones

Perks & Benefits: 

• Medical, dental, and vision insurance 
• 401(k) plan 
• Paid time off 
• Flight benefits through our airline partners 
• Company-paid life insurance 

Location: 
Remote, with up occasional travel to station locations in the USA / Canada. Residents of New York City, Philadelphia, Boston and Toronto are preferred.

Schedule: 
Standard business hours local time Monday – Friday (CST, EST, MST)
 
The Landline Company is proud to be an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, national origin, disability, or protected veteran status.