Customer Support Representative
Remote (Canada) | Hybrid Available – Kitchener, ON
Reports to: Manager, Customer Support
About Encircle
Encircle is leading the $1.6 trillion property insurance industry out of the dark ages of pen and paper, into the digital age of transparency and empowerment. Our easy-to-use software platform enables thousands of restoration contractors and insurance professionals across North America to process claims faster and with greater accuracy.
We’re a remote-first company with a collaboration hub in downtown Kitchener—and we’re growing.
About the Role
We’re hiring a Customer Support Representative to join our tight-knit support team. This is a Tier 1 role best suited for someone early in their support career, but with real experience supporting a SaaS product. You’ll be on the front lines helping customers—mostly over the phone and through email—solve problems, learn our platform, and get the help they need, when they need it.
We're not looking for someone who’s brand new to support—we need someone who’s ready to jump in, take ownership, and grow. Our ideal candidate is curious, thoughtful, and confident enough to say, “I don’t know, but I’ll find out.” You’ll work independently day-to-day but will also collaborate often with our sales, success, and development teams.
Key Responsibilities
- Become deeply familiar with the Encircle platform so you can support all areas of the product—not just a single feature
- File bug reports in Jira and communicate issues effectively to the dev team
- Recognize patterns in customer issues and raise a flag when something looks off (yes, you’ll help decide when we call an incident)
- Use Zendesk to manage tickets and phone support with attention to detail and process
- Work cross-functionally with Success, Sales, and Product to ensure smooth customer experiences
- Use our internal and external knowledge base to educate yourself, and ask questions when something doesn’t make sense
- Suggest and test improvements to our processes—don’t be afraid to take your head out of the queue and help us think bigger
- Help create documentation and training content to support our customers and internal team
- Be available for occasional Saturday and holiday coverage (rotation basis)
✅ What You Bring
- 2–3 years experience in a customer support role, ideally in a SaaS B2B environment
Strong communication skills—written and verbal—with a calm, professional phone presence (Bonus if you’re French/English bilingual) -
Comfortable navigating technical conversations and learning new tools - A habit of thinking critically before jumping into solution mode
- Comfortable working independently while staying aligned with the team
- Ability to self-serve through documentation, and the humility to ask for help when needed
- Experience with Zendesk, Jira, or other customer support tools is a bonus
- Familiarity with the restoration, construction, or insurance industry is a nice-to-have—but we’ll help you get there
Be Part of Something Special
We’re a small, mighty team supporting a large, fast-growing customer base. You won’t just be another name in the queue—you’ll be a key part of our customer experience and part of a company that values long-term growth. We’re not just offering a job. We’re offering a career path.
Our customers are the ones showing up after hurricanes, wildfires, and floods to help homeowners when they need it most. What we do matters—and we take pride in supporting the people doing that essential work.
HOURS OF OPERATION
- Monday–Friday, 9:00 AM–5:00 PM ET
- Some Saturday and holiday on-call (rotation basis)
Why Encircle?
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Balance: Flexible hours, self-managed vacation, and trust to manage your time
- Remote-first: Work where you’re most productive—with access to our collaboration hub in Kitchener
- Growth-oriented: We support your learning and career development
- Well-being: We care about the full human—inside and outside of work
Encircle is an equal opportunity employer committed to building a diverse and inclusive team. We encourage all qualified candidates to apply and will work with applicants to accommodate accessibility needs throughout the hiring process.
