York Region District jobs

BusPlanner is hiring a Customer Success Manager to manage and grow relationships with school districts across Canada. This is a hybrid role that combines account growth and customer support, ideal for someone who is proactive, highly energetic, relationship-focused, and excited to drive impact in the education space.

You’ll serve as the primary contact for our Canadian clients, ensuring they’re getting maximum ROI from our all-in-one transportation management suite and working in tandem with our support team to troubleshoot issues. At the same time, you’ll be responsible for renewals and upsells.

This role is best suited to someone based in the GTA, ideally with familiarity in public sector or education environments. Travel will be required, including occasional client visits and conference attendance across Canada.

Why BusPlanner?

BusPlanner is the leading provider of student transportation management software in Canada. Our platform is used by hundreds of the largest school boards and consortia from coast to coast (Toronto District School Board, York Region District School Board, Peel Region School Board, and many others), helping optimize bus routes, manage planning and operations, and streamline communication between school transportation teams and families.

We are a proud Canadian company with deep expertise in K–12 education and a proven track record of supporting the unique needs of Canadian school districts. We are scaling rapidly and investing in growing our customer-facing team to better serve our clients from British Columbia to Newfoundland.

BusPlanner’s leadership team consists of seasoned entrepreneurs who have significant experience in building and growing multiple successful software businesses including: (i) FieldEdge, a leading provider of software for the field services market which the team grew more than 5x and sold to a mega-cap private equity fund, and (ii) AutoLeap, a leader in the auto repair software market that has raised more than $50 million from some of the most reputable VC firms in Silicon Valley.

This is a rare opportunity to join a purpose-driven team at the heart of Canada’s education technology ecosystem.

Requirements

As a successful CSM, you will:

• Act as the primary post-sale contact for Canadian school boards, supporting them across onboarding, training, usage, and renewal.
• Conduct proactive health checks and account reviews to drive engagement, satisfaction, and adoption of the BusPlanner platform.
• Identify and close expansion opportunities, including new modules, features within an existing board.
• Manage renewals and hit sales quotas tied to growing Annual Recurring Revenue (ARR) from your assigned accounts.
• Coordinate with our in-house Support Team to resolve service tickets and help customers navigate technical issues.
• Participate in Canadian education and transportation conferences, building relationships and staying close to market needs.
• Maintain accurate records of client interactions, pipeline, and account activity.

You Should Apply If:

• You are based in Ontario, Canada, with an understanding of (or willingness to learn) the K–12 education system and how Canadian school boards operate.
• You are entrepreneurial and resourceful — you take initiative, adapt quickly, and enjoy solving complex challenges.
• You are sales-minded — you're comfortable identifying opportunities, managing a pipeline, and closing deals.
• You are service-oriented — you value strong relationships and want your customers to succeed.
• You are organized and responsive — you balance customer needs and internal responsibilities with ease.
• You are a confident communicator — you’re comfortable presenting to senior stakeholders, in person or virtually.

You Should Not Apply If:

• You prefer highly structured environments with rigid processes and step-by-step instructions.
• You are uncomfortable juggling both sales and customer-facing responsibilities in the same role.
• You are looking for a job where you can stay behind the scenes — this role involves direct interaction with school board leaders and decision-makers.
• You are not comfortable taking ownership, following up proactively, or working with some ambiguity.
• You’re not open to learning about a complex industry like student transportation or the Canadian public education system.

Preferred Qualifications

• 2–4+ years in customer success, account management, or sales, ideally within Canadian SaaS, edtech, or govtech environments.
• Experience working with school boards, transportation consortia, or public sector organizations in Canada is a strong asset.
• Familiarity with student transportation or K–12 operations in Canada is helpful, but not required.
• Willingness to travel within Canada for client visits and to Waterloo, Ontario for onboarding and team sessions.
• Strong communication and presentation skills — comfortable leading demos, training sessions, and account reviews.
• Ability to manage a large and varied client portfolio, including proactive and reactive support.
• French language proficiency is a plus, especially for Québec and New Brunswick accounts.
• Comfortable collaborating with technical teams and helping clients troubleshoot common usage issues.