Manager, Customer Support

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.

Rewind is looking for a Manager of Customer Support to lead and scale our support operations across Tier 1 and Tier 2 functions.

This role is ideal for a customer-centric, operational leader who thrives on building efficient systems, coaching high-performing teams, and leveraging AI to drive excellence. You’ll oversee day-to-day support operations, guide a growing team of specialists, and continuously refine systems and workflows to deliver fast, friendly, and frictionless customer experiences.

What you’ll do

Team leadership & development

• Lead, coach, and inspire a distributed Customer Support team through regular 1:1s, feedback sessions, and skill-building initiatives.

• Foster a culture of learning, accountability, empathy, and psychological safety where team members feel supported to grow and experiment.

• Jump into the queue regularly to stay close to customer issues and model best practices as a hands-on leader.

• Manage performance metrics including CSAT, SLA adherence, first response time, and resolution rates.

• Empower team members through data-driven coaching, development conversations, and growth opportunities.

• Recognize and celebrate wins while addressing performance gaps with empathy and clarity.
  

Quality assurance & continuous improvement

• Maintain and improve a robust QA program, including regular ticket reviews, calibration sessions, and quality audits.

• Provide constructive feedback on ticket quality, tone, accuracy, and efficiency.

• Use QA insights to identify coaching opportunities, knowledge gaps, and process improvements.

• Create a feedback loop between QA findings and training initiatives.
  

Operations & process optimization

• Serve as Zendesk administrator, building and maintaining workflows, automations, macros, triggers, and views.

• Design and implement AI-powered support tools using platforms like n8n, Claude, and other emerging technologies.

• Develop and maintain internal documentation in Guru and other knowledge bases.

• Create dashboards and reporting systems to track performance and surface insights for optimization.
  

Cross-functional collaboration

• Partner with Product and Engineering to share customer feedback, manage technical escalations, and advocate for product improvements.

• Work with Sales and Revenue Operations to ensure smooth handoffs and a consistent customer experience.

• Contribute to retention and engagement strategies through proactive support initiatives.
  

Technical systems management

• Maintain and optimize Zendesk and its integrations with internal systems.

• Build and refine automation workflows to reduce manual effort and improve response times.

• Experiment with AI tools (chatbots, AI-assisted responses, and workflow automation) to scale customer interactions.

• Ensure data accuracy and integrity across support systems and CRM.

What you’ll bring

• 5+ years of experience in customer support within B2B SaaS.

• 3+ years of people leadership experience in support operations.

• A player-coach mentality — comfortable rolling up your sleeves to handle tickets and support the team during high-volume periods.

• Advanced Zendesk administration skills and comfort configuring automations and reporting.

• Strong QA mindset with experience building quality assurance programs and coaching for improvement.

• Experience implementing AI or automation tools to streamline workflows.

• Strong analytical and data-driven decision-making skills.

• Excellent communication and a genuine passion for empowering both customers and teams.

• Ability to balance operational efficiency with team morale and individual growth.
  

Nice to have

• Experience with workflow automation tools like n8n, Zapier, or similar.

• Familiarity with AI/LLM tools (Claude, ChatGPT, custom GPTs).

• Knowledge of knowledge base platforms (Guru, Notion, Confluence).

• Experience with Salesforce or other CRM systems.

• Background in technical support or developer-focused products.
  

Location and working hours

This is a hybrid role based in Ottawa or Toronto. Occasional travel for team off sites may be required.

Why join Rewind

At Rewind, you’ll join a company that’s redefining how businesses protect and recover their data. We value curiosity, accountability, and innovation — and we trust our people to experiment and grow. You’ll work alongside a team that’s passionate about customer success, respectful of your time, and committed to making a positive impact in our industry and community.

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

• 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.