Tri-Board Student Transportation Services is conducting an Executive Search for a Chief Executive Officer. Tri-Board Student Transportation Services is responsible for providing, safe, secure, and on-time transportation for the Algonquin & Lakeshore Catholic District School Board, the Hastings & Prince Edward District School Board, and the Limestone District School Board. Tri-Board is seeking a collaborative and relationship focused leader who thrives in a dynamic community-facing environment. Reporting to a Board of Directors, the Chief Executive Officer is responsible for fostering a culture of safety for student transportation, overseeing operational excellence and leading the Tri-Board team with integrity and strategic focus. This position plays a key role collaborating with the school boards, including Principals, Senior Administration, Trustees, and key external stakeholders.
Key responsibilities include, but are not limited to:
- Analyze the transportation system and policies for each Board with a view to maximizing effectiveness and efficiencies within provincial and Board requirements
- Expand and foster community and public relations in the provision of student transportation
- Prepare statistical, financial, and administrative reports supporting provincial government funding calculations
- Conduct annual Ministry routing simulations as part of Ministry’s student transportation funding allocation process
- Attend Board and Committee meetings related to the transportation system
- Ensure the efficiency and integrity of the comprehensive routing system and computerized mapping system
- Act as the spokesperson concerning matters related to school bus transportation, appeals from parents/guardians and other decisions in consultation with senior administration of the district school boards
- Consult with the district school boards regarding inclement weather cancellations
- Remain current and ensure compliance with the Ministry of Transportation legislation and regulations related to school transportation, particularly the Ontario Highway Traffic Act
- Represent Tri-Board on the Ontario Association of School Business Officials (OASBO) – Transportation Committee and the Provincial Government – Transportation Review Committee
- Oversee the annual budget process, including budget estimates, quarterly expenditure forecasts and the annual transportation budget
- Manage a competitive procurement process and negotiate school bus transportation contracts
Qualifications:
- A university degree in business, geography, planning or a related field
- A minimum of 5 years progressive management experience in a transportation related environment, preferably in a school district, bus transportation company or municipality
- Excellent communication skills, experienced in report writing and at ease presenting to a small or large audience
- An effective team builder with experience developing and coordinating system wide initiatives
- A strategic and visionary leader who embraces “out -of-the-box” thinking, recognizing safety is of utmost importance
- Demonstrated experience leading in a unionized environment, developing policy and negotiating service contracts
- A high-level of expertise in operations and managing a large budget
- A commitment to learning and professional development • Proficiency using standard business and related software applications (knowledge of BusPlanner is an asset)
- Valid driver’s licence and use of a personal vehicle is required
Tri-Board Student Transportation Services offers a rewarding work environment, a competitive salary, extended health benefits, generous vacation entitlements, and OMERS pension. Salary range is $146,505 to $160,000 and will be commensurate with qualifications and experience.
To apply, please forward a cover letter and resume in confidence to [email protected] by 2:00 p.m. (est) Friday, August 14, 2026. Only those applicants who are invited to proceed to the next level of the selection process will be contacted.
Tri-Board is committed to creating an inclusive, equitable and accessible workplace. Applicants who require accommodations at any point in the recruitment and selection process are encouraged to reach out through the above email.
