Part Time Chat Support Remote Jobs in Toronto, ON

Location: Greater Toronto Area preferred; open to candidates elsewhere in Ontario
Type: Part-time, Casual, Subcontractor
Reports to: Customer Support Manager

Closing Date: July 24, 2026

We're the team behind Messenger Pigeon, our flagship app used by students/learners everywhere, along with a growing suite of other products. We believe great support is human support. While a lot of companies are racing to automate their customer service away, we're doing the opposite — investing in real people providing accommodative supports because we believe that's the best way to help our users in a meaningful way.

We're looking for Customer Support Associates who can take a patient approach to problem-solving to join our team. You will be working as frontline contacts to offer live, realtime support across phone, live chat, and email — helping our users (many of whom are students/learners) navigate Messenger Pigeon and our other products.

This isn't a script-reading, ticket-closing kind of support job. Many of our users have disabilities, and we listen to gain insight to the barriers our users experience and support them accordingly. Successful incumbents will be those willing to take real pride in helping people, not just resolving cases as quickly as possible.

• Provide primary support for Messenger Pigeon, our flagship app, along with support for our other products as needed
• Respond to user inquiries across phone, live chat, and email in a timely, friendly, and professional manner
• Problem solve, troubleshoot issues, answer questions, and guide customers to solutions with patience and clarity
• Escalate complex or unresolved issues to the appropriate team when needed
• Document user interactions and feedback to help us continuously improve our products and support experience
• Help plan and facilitate workshops for our users, sharing tips and best practices for getting the most out of our products
• Contribute to a team culture that values empathy, care, and genuine human connection over speed metrics alone
  

• You will be part of a team consisting of three associates dedicated to providing excellent support in a timely and effective manner.
• Associates are expected to attend all their assigned shifts, as determined by the manager.
• All associates are expected to complete all mandatory training before starting in the field.
• Pay will range between CAD$23 and CAD$26 per hour. This role is not salaried as chosen candidates will be sub-contracted.

Requirements

• The ability to remain composed, compassionate, and focused on finding solutions, even when interacting with a frustrated user.
• Strong written and verbal communication skills
• Experience working with people with disabilities in an academic environment or willingness to learn
• Comfort working across multiple channels (phone, chat, and email) throughout the day
• Knowledge of accessibility legislation (i.e.AODA) or willingness to to learn
• Fluency in English required; bilingual fluency (English/French) is a strong asset.
• Based in the Greater Toronto Area preferred; candidates elsewhere in Ontario are welcome to apply
• Candidates have to be eligible to work in Canada and be located in the country.
• Comfortable working on Apple devices, all company-issued equipment runs on macOS and iOS. If you strongly prefer Windows or Android, this role may not be the best fit.
• Experience with Intercom is an asset
• Required familiarity/fluency with Windows, MacOS, iOS and Android, as well as ChromeOS, since our customers use all kinds of devices

.What to Expect - Application Process

• There will be two rounds of interviews
• We appreciate all applicants who have chosen to apply, but only those chosen for interviews will be contacted. Thank you for your interest in this role!
• We will be accepting applications for three individuals for this role.

Habitat Learn is an equal opportunity employer. We welcome applications from all qualified candidates, including people with disabilities. Accommodations are available upon request throughout the recruitment process.

Benefits

We're a company that believes support should feel human. You won't be measured purely on call times or ticket volume — you'll be trusted and supported to take the time each customer actually needs. If you care about people and want to work somewhere that backs that up with real investment in its support team, we'd love to hear from you.