<p>Assistant Transportation Manager JobID: 2709</p> <p>Position Type:</p> <p>Transportation</p> <p>Date Posted:</p> <p>11/26/2025</p> <p>Location:</p> <p>Transportation</p> <p>Date Available:</p> <p>02/02/2026</p> <p>&nbsp&nbspAdditional Information: Show/Hide</p> <p>Assistant Transportation Manager: 12-Month Position</p> <p>Cheshire Public Schools</p> <p>THE POSITION</p> <p>The Assistant Transportation Manager is responsible for supporting the Transportation Manager in overseeing and managing all aspects of school transportation within Cheshire Public Schools, ensuring that students are safely and efficiently transported to and from school, extracurricular activities, and special events.</p> <p>The Assistant Transportation Manager will support the Transportation Manager in managing the district's fleet of school buses, supervising drivers and support staff, coordinating routes, ensuring compliance with safety regulations, and maintaining budgetary control over transportation-related costs. The Assistant Transportation Manager will also work closely with district administrators, school principals, parents, and the community to ensure high levels of service and safety.</p> <p>There is strong potential that the person selected for this position, if they perform the responsibilities of the job, may be promoted in the future to assume the position of Transportation Manager upon the retirement of the person currently serving in the role.</p> <p>REPORTS TO: Transportation Manager</p> <p>STATUS: Exempt</p> <p>KEY RESPONSIBILITIES</p> <ul> <li> <p>Fleet Management & Operations</p> </li><li> <p>Coordinate the daily operations of the district's school bus fleet, including maintenance, scheduling, and safe operation.</p> </li><li> <p>Support in the development of safe bus routes to ensure timely arrivals and departures.</p> </li><li> <p>Monitor the condition of buses and coordinate regular inspections, repairs, and preventive maintenance.</p> </li><li> <p>Ensure compliance with state and federal transportation regulations, including vehicle safety standards, inspections, and certifications.</p> </li><li> <p>Driver Management & Training</p> </li><li> <p>Support the supervision, training, and evaluation of transportation staff to ensure they adhere to district policies, safety standards, and best practices.</p> </li><li> <p>Coordinate the recruitment, hiring, and scheduling of bus drivers and support staff.</p> </li><li> <p>Implement and enforce district and state safety regulations for student transportation, including emergency response procedures and safety drills.</p> </li><li> <p>Route Planning & Scheduling</p> </li><li> <p>Support the planning of bus routes for all school activities, ensuring maximum efficiency and cost-effectiveness while meeting safety and student needs.</p> </li><li> <p>Review and update bus routes periodically to accommodate changes in student enrollment, school locations, and special events.</p> </li><li> <p>Coordinate with school principals, extracurricular program leaders, and parents to ensure adequate transportation for field trips, athletic events, and other special activities.</p> </li><li> <p>Safety & Compliance</p> </li><li> <p>Ensure all transportation operations comply with local, state, and federal regulations (e.g., Department of Transportation, school bus safety laws, child safety seat requirements).</p> </li><li> <p>Assist with safety checks, inspections, and audits to ensure that vehicles, equipment, and drivers meet all regulatory standards.</p> </li><li> <p>Support safety training for drivers and staff, focusing on student behavior management, emergency procedures, and vehicle safety.</p> </li><li> <p>Budget & Financial Oversight</p> </li><li> <p>Support the development and management of the transportation budget, tracking expenditures for fuel, maintenance, staffing, and other related costs.</p> </li><li> <p>Identify opportunities to reduce costs, improve efficiency, and plan for future budget needs (e.g., fleet replacement, route optimization).</p> </li><li> <p>Prepare reports for the Transportation Manager, Chief Operating Officer, and the Superintendent on transportation expenditures and performance.</p> </li><li> <p>Customer Service & Communication</p> </li><li> <p>Assist as a point of contact for parents, school staff, and the community regarding transportation concerns, route changes, and student behavior on buses.</p> </li><li> <p>Address transportation-related issues or complaints in a timely, professional manner.</p> </li><li> <p>Maintain open lines of communication with district leadership, school principals, and other departments to ensure smooth operations.</p> </li><li> <p>Technology & Reporting</p> </li><li> <p>Utilize transportation management software and other technology tools to track and manage bus routes, driver schedules, and student ridership.</p> </li><li> <p>Prepare regular reports on transportation performance, including timeliness, safety, and cost efficiency.</p> </li><li> <p>Stay up-to-date with technology trends in transportation, including GPS tracking systems and route optimization software.</p> </li><li> <p>Additional Duties</p> </li><li> <p>Perform all other related duties, as needed, for the purpose of ensuring the efficient and effective functioning of the Human Resources Department and the Office of School District Operations.</p> </li><li> <p>Note: The above description is illustrative of essential functions for this position. It is not meant to be all inclusive of every task or responsibility.</p> </li></ul> <p>PHYSICAL DEMANDS</p> <ul> <li> <p>Ability to lift and carry up to 25 pounds.</p> </li><li> <p>Ability to conduct safety checks and inspections on buses and other vehicles.</p> </li><li> <p>Ability to drive school vehicles of various sizes and capacities.</p> </li><li> <p>Travel between schools, bus yards, and other locations.</p> </li><li> <p>Ability to work outside in varying weather conditions.</p> </li></ul> <p>TRAVEL REQUIREMENTS</p> <ul> <li> <p>This is a fully on-site position.</p> </li><li> <p>Work will be performed in both office and field environments, including school bus yards and bus stops.</p> </li><li> <p>The position may require occasional evening or weekend hours to attend meetings, special events, or resolve transportation-related issues.</p> </li></ul> <p>KNOWLEDGE, SKILLS, ABILITIES</p> <ul> <li> <p>Strong leadership, organizational, and interpersonal skills, with the ability to manage a diverse team of drivers and staff.</p> </li><li> <p>Excellent problem-solving abilities, especially in dealing with safety issues, schedule changes, or student-related incidents.</p> </li><li> <p>In-depth knowledge of school transportation regulations, vehicle maintenance, and route planning.</p> </li><li> <p>Proficient in the use of transportation management software and Microsoft Office Suite.</p> </li><li> <p>Ability to manage a budget, track expenditures, and identify cost-saving opportunities.</p> </li><li> <p>Strong communication skills, both verbal and written, for interacting with district personnel, parents, and the community.</p> </li></ul> <p>QUALIFICATION PROFILE</p> <ul> <li> <p>A high school diploma is required. A college degree in business, public administration or personnel management is desired but not essential for candidates who have sufficient experience and a solid performance record in transportation manager.</p> </li><li> <p>Bachelor's degree in transportation management, logistics, business administration, or a related field (preferred).</p> </li><li> <p>Experience in managing a fleet of vehicles, ideally in a public sector or school environment.</p> </li><li> <p>Knowledge of federal, state, and local regulations related to school transportation and safety.</p> </li></ul> <p>CERTIFICATIONS</p> <ul> <li> <p>V-endorsement</p> </li><li> <p>Valid commercial driver's license (CDL) with appropriate endorsements (preferred but not required).</p> </li><li> <p>CPR/First Aid certification (or willingness to obtain).</p> </li></ul> <p>SALARY</p> <p>The salary range for this role is between $55,000 to $62,000.</p> <p>Cheshire Public Schools - A Great Place to Work</p> <p>Cheshire Public Schools is a great place to work where you can grow professionally and find personal satisfaction as you help to support our mission to provide high quality education to inspire lifelong learning and service to others. Our commitment to excellence shines through every aspect of our award-winning curriculum, culture, and community. Go to our website at https://www.cheshire.k12.ct.us/district-departments/human-resources/why-work-for-us/ to learn more about our award winning health and wellness benefits and why we are a great place to work.</p> <p>To Apply: Please apply online at www.applitrack.com/cheshire/onlineapp</p> <p>Cheshire Public Schools reserves the right to close the posting when a suitable applicant is found before the closing date.</p>