Customer Support Specialist

Rewind is a service that protects the critical data that powers businesses of all sizes. Our focus is on backing up data that lives in the cloud - in apps like Jira, GitHub, Confluence and Shopify. We are backed by Insight Partners, Inovia, Bessemer and Atlassian Ventures and are proud to be recognized as one of Canada's 50 fastest growing technology companies (2023 Deloitte Fast 50). We invite you to read our startup story to learn where we came from and where we’re going.

Read about our mission, story and values here.

To find out more about our perks, click here.

Some of our Blogs might help you get a better understanding of what we do here. You can find them all here.

Thriving At Rewind

We embrace the fast-paced, ever-changing nature of startup life. If you love working with speed, agility, and creativity, you’ll feel right at home here. Here's what it takes to succeed with us:

• Team-First Mentality: We put teamwork at the core of everything we do, believing that we are better when we are together. Success is shared, and when the team wins, we all win.
• Performance-Driven Mindset: We are proactive, goal-oriented, and focused on delivering tangible, high-quality results. We go beyond meeting expectations - we aim to exceed them.
• Flexible Work-Life Approach: We encourage balance and understand the need to recharge. While we stay agile for urgent needs, we make sure there's time to recover and enjoy life.
• Customer Centricity: Our commitment to customers shapes everything we do. We listen, build relationships, and innovate - from our dedicated customer support team to our engineers, everyone at our company is focused on solving problems that matter most to our users.
• Taking Initiative: We value ownership and proactive problem-solving. We encourage team members to think creatively, take ownership, and lead improvements. Your ideas and actions drive our success.
• We Make Time for Fun: We work hard and make time to enjoy the journey. It’s not just about hitting milestones—it’s about making the experience rewarding along the way.
  
  

Job Description

We’re looking for a Customer Support Specialist who brings deep empathy, strong B2B experience, and the ability to support customers with confidence, clarity, and ownership. You’ll be on the front lines of a fast-paced support team where project work is the norm, change happens quickly, and every team member is empowered to shape how support works at scale.

You’ll support a wide range of customers, from SMBs to enterprise accounts, and be a critical part of the customer journey. That means communicating with care, troubleshooting with precision, and creating strong feedback loops between customers and internal teams. You’ll need to be comfortable navigating evolving workflows, balancing customer empathy with business impact, and operating with a strong sense of ownership in everything you do.

There’s also room to grow into specialized domains. Experience with billing workflows (subscriptions, payments, invoices) is a nice-to-have—not a requirement—but if you have an interest in becoming a subject matter expert in that area, we’d love to help you get there.

Your Day-to-day Will Include

• Delivering thoughtful, high-quality customer support via email, live chat, and phone when necessary (we do not provide inbound phone support but will happily jump on a call to resolve issues when necessary).
• Taking full ownership of issues from initial report to resolution, escalating only when needed and always with full context.
• Supporting a variety of users, including technical and non-technical personas, across a global B2B customer base.
• Managing your workload with autonomy—balancing fast triage with deep problem-solving as needed.
• Working closely with Engineering, Product, and other internal teams to flag bugs, clarify expected behavior, and relay customer insights.
• Contributing to internal and external documentation, macros, and process improvements.
• Participating in team initiatives and special projects that improve how support operates.
• Collaborating with your peers to build a strong, inclusive support culture grounded in accountability and continuous learning.
• Ability to work some holidays as part of a rotating coverage schedule along with a monthly on-call rotation for weekend premium support requests.
  
  

What We’re Looking For

You should have at least 1–3 years of experience in customer support, ideally within a B2B SaaS startup or scale-up, as well as experience working with mid-market or enterprise customers—especially in contexts where premium support or SLAs were in place.

You Also Have

• Excellent communication skills - clear, empathetic, and appropriately technical based on audience.
• A proactive, ownership-driven mindset. You spot inefficiencies, raise ideas, and take initiative to improve.
• Comfort with ambiguity, change, and wearing multiple hats in a growing environment.
• Technical curiosity—enough to dig into product behaviors, replicate customer issues, and provide actionable context to engineering.
  
  

Bonus points if you…

• Have experience supporting billing issues such as invoicing, payment errors, or subscription changes.
• Have worked with tools like Zendesk, Salesforce, Slack, Stripe, or Jira.
• Have contributed to help centers, internal knowledge bases, or automation projects.
  
  

Additional Information

Where You’ll Work

Our organization follows a hybrid work structure where employees work from the office three days/week. This role will be based out of our Toronto office.

How Rewind Will Support You

We know that enjoying the journey is just as important as reaching our goals. We work hard to create a positive, inclusive environment where fun and laughter are part of our everyday routine. We also offer a variety of benefits to support your success both at work and in your personal life which includes but is not limited to:

• Flexible work hours
• Employee stock options
• Health benefits
• 3 weeks vacation
• 7 life leave days
• 2 Level Up days for professional development
• 1 volunteer day
• Summer Fridays and office closed during the holiday break in December
• 4 week sabbatical after 4 years with us
• Paid parental leave
• $5000/year professional development allowance (you can take courses, buy books, attend conferences, cover certifications, etc)
• $1000/year wellness/home office allowance
  
  

Rewind is committed to building an inclusive, supportive place for you to do the best and most rewarding work of your career. We value how each new hire is an opportunity for us to bring in a different perspective, and we are always eager to further diversify our company. We strongly encourage candidates of all different backgrounds and identities to apply.