Transportation Manager

If you are unable to complete this application due to a disability, contact this employer to ask for an accommodation or an alternative application process.

Full Time Worcester, MA, US

3 days ago Requisition

Salary Range: $52,000.00 To $53,560.00 Annually

The Briarwood Community – Worcester, MA

Proudly rated the #1 Continuing Care Retirement Community in Massachusetts by Newsweek Magazine for the past three years, The Briarwood Community offers a supportive, mission-driven environment where employees are respected, valued, and empowered to succeed.

Join a collaborative team where your work directly supports operational excellence and exceptional resident service.

• Weekly Pay
• Paid time off and holidays
• Health, dental, vision, life, and disability insurance.
• 401(k) retirement plan with employer match
• Meal discounts and Employee Assistance Program
• Free access to indoor lap pool, fitness center, and sauna
• Supportive, collaborative team environment in a beautiful, well-maintained community

The Transportation Manager is responsible for overseeing the daily operations of the Briarwood transportation department while serving as an active driver. This position provides leadership to the transportation team, ensures safe and efficient transportation services, maintains fleet compliance, and supports residents and staff throughout the community.

The Transportation Manager works closely with the Concierge Team, which provides transportation scheduling and logistical direction. This role is responsible for executing transportation plans, supporting drivers, maintaining vehicles, and ensuring all transportation services are delivered safely and professionally.

Position Type: Full Time

Salary Range: $52,000 - $53,560 Annually

Schedule: Primarily Monday through Friday (Must be available for occasional early mornings, evenings, weekends, or emergency coverage as needed)

• Oversee the daily operations of the transportation department to ensure safe, efficient, reliable, and resident-focused transportation services.
• Provide leadership, supervision, coaching, and support to transportation staff, including performance management, corrective action, and ongoing development.
• Drive residents to medical appointments, community outings, special events, and other destinations as needed, and provide transportation coverage during staffing shortages.
• Coordinate transportation schedules and logistics in partnership with the Concierge Team, ensuring timely communication of schedule changes, transportation requests, and service updates.
• Train, coach, and monitor drivers to ensure compliance with transportation policies, safe driving practices, wheelchair securement procedures, emergency protocols, vehicle operation standards, and exceptional resident service.
• Maintain driver records, including licenses, certifications, training documentation, background checks, and other required compliance files, ensuring adherence to insurance, regulatory, and community requirements.
• Oversee fleet operations, including vehicle maintenance, inspections, registrations, preventive maintenance, repairs, and service scheduling.
• Ensure all transportation vehicles are clean, safe, properly equipped, fueled or charged, and ready for daily operation.
• Maintain transportation records, mileage logs, billing information, reports, expenses, and other departmental documentation.
• Ensure compliance with all applicable local, state, federal, and community transportation regulations and safety standards.
• Investigate and respond to transportation incidents, accidents, service concerns, and operational issues, implementing effective corrective actions as needed.
• Coordinate with vendors, repair facilities, and service providers to maintain fleet reliability and operational readiness.
• Collaborate with departments throughout the Briarwood continuum to support resident transportation needs, community activities, special events, programs, and continuum-wide initiatives.
• Demonstrate flexibility and a team-oriented approach by assisting with operational needs, special events,…