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Safety & Training Supervisor

Overland Park, Kansas
The Safety & Training Supervisor is responsible for ensuring the safe, compliant, and professional operation of our passenger-transport services in the Kansas City market. This role combines hands-on field supervision, driver coaching, new-hire training, operational support, and occasional coverage of Manager-on-Duty responsibilities.
This position is ideal for someone who thrives in a safety-first culture, has strong leadership presence, and can coach and support drivers while upholding company standards and DOT compliance requirements.

Key Responsibilities

Safety & Compliance

  • Conduct safety checks, site checks, yard hazard assessments, and ride-alongs
  • Evaluate driver performance and provide coaching based on camera events and incident data
  • Conduct initial and recurring safety training sessions
  • Participate in accident/incident investigations, reporting, documentation, and follow-up
  • Support DVIR compliance reviews and support vehicle condition reporting
  • Enforce fit-for-duty standards and fatigue-management protocols
  • Promote strict adherence to DOT regulations, HOS, and company policy
  • Support safety culture — accountability, documentation, follow-through

Training & Development

  • Train new drivers on operational procedures, company standards, and safety expectations
  • Support passenger endorsement training when applicable
  • Document training progress and maintain certification records
  • Conduct check rides and performance assessments
  • Facilitate ongoing refresher and corrective training

Operational Support

  • Assist dispatch, operations, and field logistics as needed
  • Help coordinate bus staging and parking at service locations
  • Communicate delays, route issues, and service impacts
  • Support customer-facing interactions in a professional and service-oriented manner
  • May cover Manager on Duty (MOD) shifts up to ~2 times per week, when required
  • Provide real-time field visibility and reporting to leadership

Required Qualifications

  • Prior experience in transportation operations, safety, training, or supervision
  • Strong situational awareness and decision-making skills
  • Ability to coach and communicate with drivers in a constructive, supportive manner
  • Strong understanding of DOT & FMCSA compliance (or willingness to learn quickly)
  • Professional writing and documentation abilities
  • Ability to remain calm and directive during incidents or service interruptions
  • Must pass pre-employment screening and background checks

Preferred Qualifications

  • CDL Driver’s License (Class B), preferably with Passenger Endorsement
  • Experience in fleet operations, bus/shuttle transportation, or logistics
  • Familiarity with Samsara or similar telematics/camera systems
  • Accident/incident investigation experience
  • Safety or compliance-related certifications

Schedule

This role may include:
  • Early mornings
  • Mid-day operational coverage
  • Occasional evenings
  • Split-shift flexibility
  • MOD coverage as needed
We transport essential-service employees — reliability and punctuality are critical.

Compensation & Benefits

  • Competitive hourly or salary range
  • Eligible for performance- and safety-based bonuses
  • PTO and paid holidays
  • Career-path advancement opportunities within our growing organization
  • Training support to grow into higher-level leadership roles
About My Ride to Work
My Ride to Work is a complete transportation solution provider leveraging workforce management strategies, technology and data analytics.  We have over 20 years in the outsourcing industry where flexibility and reliability are equally important. Our management teams, ground crew and professional drivers have a deep understanding of and experience in the transportation industry.  We partner with companies to understand their objectives and create ridership and route programs that support specific workforce needs with an emphasis on safety, rider experience and comfort.

My Ride to Work is an equal opportunity employer.  No employee or applicant will be discriminated against in any condition of employment because of race, color, national origin, sex, religion, age, disability, veteran status or any other status protected by law. 

We are an E-Verify Employer.

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