Senior Operations & Safety Supervisor (CDL with P Endorsement Preferred)

Senior Operations & Safety Supervisor (CDL with P Endorsement Preferred) Joseph's Transportation Medford, MA Job Details Full-time $65,000•$80,000 a year 16 hours ago Benefits Health insurance Dental insurance Paid time off Vision insurance Qualifications

CDL B FMCSA

(Federal Motor Carrier Safety Administration) regulations Operations management Incident management Passenger Endorsement Staff scheduling Telematics Microsoft Office Fleet compliance management Dispatching Transportation compliance audits implementation Full Job Description 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