Transportation Manager

The Briarwood Community –  Worcester, MA

About The Briarwood Community

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.

Why Join Us?

Position Summary

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)

Responsibilities

• 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 andlogisticsin partnership with the Concierge Team, ensuringtimelycommunication 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,fueledor 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 tomaintainfleet 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 byassistingwith operational needs,special events, community initiatives, and other responsibilities as business needs require. 
• Perform other duties and special projects as assigned. 

Qualifications

Required

• High School Diploma or equivalent required
• Previoustransportation, fleet management, supervisory, or related experience preferred
• Valid driver's license with a clean driving record
• Must be eligible to be covered under the Briarwood automobile insurance policy
• Strong leadership and team-building skills
• Excellent communication and customer service abilities
• Strong organizational and documentation skills
• Ability to train, coach, and support staff
• Ability to work independently and make sound decisions

Preferred

• Strong leader who can support both staff and residents
• Ability to take direction and work collaboratively with multiple departments
• Patient, calm, and safety-focused approach
• Must be able to adapt to changing schedules and priorities
• Commitment to teamwork, professionalism, and exceptional resident service

About Our Community

The Briarwood Community is a nonprofit Continuing Care Retirement Community (CCRC) serving older adults throughout the Greater Worcester area since 1984.

Our campus includes independent living, assisted living, memory care, and skilled nursing services — all designed to support residents through every stage of retirement living.

At Briarwood, our employees are part of a compassionate team dedicated to enhancing the physical, social, and spiritual well-being of every resident we serve.