Senior Operations & Safety Supervisor (CDL - P Endorsement Highly Preferred)

Location: Medford, MA 02155

Schedule: Monday – Friday, 12:00 PM to 9:00 PM (could vary based on daily trip schedule)

(Note: True ownership of this role requires after-hours accountability and availability to support ongoing operations and emergencies).

Compensation: $65,000 - $85,000/year based on experience and CDL with P

About the Role

We are seeking a highly organized, tech-savvy Senior Operations & Safety Supervisor to oversee our afternoon and evening transportation operations. This is a dynamic, hands-on leadership role that blends live dispatching, fleet management, and active driver training. The ideal candidate has deep experience in passenger transportation, a strong command of DOT/DPU regulations, and a passion for coaching drivers.

If you thrive in a fast-paced environment, take pride in running a safe, elite, and compliant fleet, and are willing to fully own the operation from top to bottom—we want you on our leadership team.

Key Responsibilities: Dispatch, Live Operations & Ownership

• Monitor live GPS and telematics (Samsara) to track fleet movements, ensure tight on-time performance, and proactively resolve on-road delays.
• Take full ownership: remaining accessible for high-level troubleshooting, driver support, or emergency escalations outside standard office hours.
• Answer incoming calls, handle customer inquiries, and direct daily communications professionally.
• Schedule drivers, assign daily routes, manage exact 15-to-30-minute passenger spot times, and manage vehicle swap-outs or emergency responses.
• Supervise drivers on duty, providing real-time guidance, support, and strict accountability.

Accident & Incident Management (Full Cycle)

• Manage the full life cycle of vehicular accidents, passenger incidents, and road emergencies.
• Direct the initial scene response, coordinate with emergency services, and guide the driver through proper company protocols.
• Oversee mandatory post-accident procedures, including securing Samsara dashcam footage, conducting internal investigations, and coordinating required DOT drug/alcohol testing.
• Complete internal incident reports and manage administrative follow-through, including filing claims with commercial insurance providers and submitting required documentation to regulatory agencies (DOT/DPU).

Safety & Driver Training

• Conduct hands-on onboarding (including a multi-day intensive training program) and continuous safety training for all drivers.
• Train staff thoroughly on the safe operation of ADA lifts, ramps, and 4-point wheelchair securement.
• Enforce the company standard for driver dress code, vehicle cleanliness, and elite customer service, holding staff accountable to handbook policies.
• Review Samsara dashcam footage to provide constructive feedback, monitor driver safety metrics, and deliver targeted safety coaching.

Fleet Readiness & Yard Management

• Oversee yard organization, assisting drivers with safe parking and enforcing the requirement to back vehicles into assigned spaces.
• Physically inspect vehicles for cleanliness, verify fueling (ensuring no vehicle sits below 5/8 tank), and ensure all buses are fully operational and presentable for service.
• Coordinate with maintenance systems (Fleetio) to log, track, and resolve vehicle defects (such as lift interlocks or door sensor faults).

Compliance & Administration

• Verify all ELDs/e-logs, pre/post-trip inspections (DVIRs), and regulatory documentation daily.
• Ensure strict compliance with DOT, FMCSA, and Massachusetts DPU regulations.
• Support administrative functions by auditing driver trip logs, verifying weekly timesheets, and resolving payroll discrepancies.

What We’re Looking For

• Licensing: Valid CDL (Class A or B) with a Passenger (P) endorsement is highly preferred.
• Systems Experience: 3+ years of hands-on experience with Samsara (required) and familiarity with Google Suite and scheduling software. Fleetio experience is a major plus.
• Industry Experience: 5+ years in Passenger Transportation Operations, Dispatch, and DOT/FMCSA compliance.
• Incident Handling: Proven experience managing accident scenes, conducting investigations, and navigating commercial insurance claims.
• Training Skills: Strong ability to teach, coach, and correct drivers, particularly regarding ADA compliance and defensive driving.
• Work Style: A dedicated self-starter capable of multitasking between office administration and hands-on yard duties, with a data-driven approach to tracking fleet safety.

Pay: $65,000.00 - $80,000.00 per year

Benefits:

• Dental insurance
• Health insurance
• Paid time off
• Vision insurance

Experience:

• Samsara: 3 years (Preferred)

License/Certification:

• Do you have a CDL with Passenger (P) Endorsement? (Preferred)

Work Location: In person