Customer Support Specialist

1 day ago

Regina, Saskatchewan, Canada Offstreet Full time

Customer Support Specialist

Offstreet is transforming guest parking with simple, scalable solution our users love, and our Customer Support team plays a key role in making that experience seamless for everyone involved.

We're not building a call center, we're building a startup-savvy, high-impact support function that works side-by-side with Customer Success, Product, and Engineering. If you're resourceful, love solving problems, and want to grow into a role with real ownership, this could be the opportunity for you.

Who You Are

You don't need years of SaaS experience, you need the right mindset. At Offstreet, we value people who are passionate, self-motivated, and resourceful. You take initiative, follow through, and thrive in fast-paced, collaborative environments. You care deeply about delivering a great customer experience. 

Support isn't just about closing tickets - it's about building trust, delivering clarity, and solving real problems.

You might be a great fit if you:

  • Are organized, dependable, and take pride in solving customer problems quickly and clearly
  • Communicate with clarity, empathy, and professionalism
  • Are excited to work with and improve existing support systems and workflows
  • Enjoy cross-functional collaboration with Customer Success, Product, and Engineering
  • Are resourceful and thrive in environments where things move quickly and priorities shift
  • See support as a core part of the customer experience, not an afterthought
  • Have experience using Freshdesk or another customer support platform, and are eager to learn more
  • Have experience with AI tools, support-desk automation, or setting up automated tasks that streamline and enhance support operations
  • Are looking to grow into more responsibility over time, whether that's onboarding, systems, or support leadership
  • Not afraid to learn how the product works under the hood (even without a technical background)

What You'll Do

As our Customer Support Specialist, you'll be the go-to for end-user inquiries and a key player in supporting new client onboarding. You'll help Offstreet scale by maintaining and optimizing support systems already in place.

  • Respond to and resolve incoming support tickets - mostly end-user inquiries (basic troubleshooting, reporting, etc.)
  • Support new client onboarding by helping set up locations, preparing signage, and assisting with training
  • Maintain and improve existing support tools, including self-serve content, knowledge base, macros, and AI-powered automation
  • Manage Freshdesk workflows and ensure tickets are efficiently categorized and resolved
  • Use integrated tools like Linear to escalate product-related issues and feedback

This is a hands-on role with variety, ownership, and opportunity to grow as the function evolves.

Why Offstreet?

We operate like a sports team, high trust, high performance, and lots of support. We're not big on hierarchy. We care about impact, good ideas, and building the best experience, for our users and each other.

In Customer Support, your work is often someone's first experience with Offstreet, and we take that seriously. You'll have ownership, real responsibility, and the chance to shape systems that grow with us. Whether you're onboarding a new client or resolving a tricky issue, your work here matters.

Ready to apply?


We're growing fast and always looking for great people. If your experience aligns with what we're building, we'll be in touch.

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