Customer Support Associate

Position title: Customer Support Associate - North America

Location: In office at 507 King Street East, Toronto. Five days a week in office, with flexibility when needed.

Hours: Monday to Friday, 10:30am to 6:30pm ET

Reports to: Head of Customer Success

Start: October 2026

We are hiring a Customer Support Associate to support schools primarily across the US and Canada. This person will be responsible for answering customer questions, investigating product issues, write and improve help centre articles, resolving what they can, and escalating more technical problems clearly.

Most of the role is customer support, with onboarding work becoming more important during peak implementation periods, especially August to October. During those months, this person will help configure new schools, support staff training and guide customers through their first weeks of live use. Over time, the goal is for this person to independently support new school implementations by the 2027 to 2028 school year.

This is an in-office role in Toronto. The person will work closely with the Support Lead, who will provide day-to-day training, direction and escalation support, and will report to the Head of Customer Success.

• Own the help-desk support queue from first response through resolution.
• Treat the help-desk as the main place you learn the product, the customer, and how support really works. The queue is not just a ticketing tool, it is where the on-the-job training happens.
• Respond to customer questions clearly, warmly and efficiently.
• Investigate issues related to account setup, permissions, imports, integrations and product usage.
• Escalate issues to engineering with clear steps to reproduce, relevant context and expected vs. actual behaviour.
• Track and improve response times, resolution quality and customer satisfaction.
• Write and improve help centre articles based on recurring customer questions.
• Identify patterns in support issues and raise them to the team.
• Review and improve the AI bot conversations and data sources.
• Take routine support questions off the Customer Success Managers’ plates.

• Take on onboarding work primarily during peak implementation periods, especially August to October.
• Configure new customer accounts, including users, groups, permissions, schedules and integrations.
• Support new customers through setup and their first weeks of usage.
• Deliver hands-on training to customer teams over Google Meet.
• Join onboarding projects from day one, with a path toward owning onboarding work independently.

We care more about how someone thinks, communicates and follows through than years of experience.

The right candidate is someone who:

• Communicates clearly in writing and on calls.
• Enjoys answering questions and helping people solve problems.
• Is comfortable saying “I don’t know” and asking for help early.
• Has a bias for action and can make progress without perfect information.
• Follows through reliably and closes the loop without being chased.
• Is technically curious and enjoys figuring out why something is not working.
• Understands that working through real customer conversations in the help-desk is a core part of learning the product.
• Can explain software patiently to non-technical users.
• Stays calm when customers are stressed or something is urgent.
• Wants to work in person and learn quickly by being close to the team.

• Retail, hospitality or front-of-house experience where the person handled real customer problems.
• Recent graduate who is organized, curious and comfortable with technology.

• Experience in schools or education.
• Teaching, tutoring, or educational background
• Familiarity with SIS platforms such as Blackbaud, Veracross, FACTS or Power School.
• Experience with tools like Intercom, Hub Spot, Salesforce or Notion.