Senior Technical Support Engineer (T3)

About the Position

Senior Technical Support Engineer (T3)

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).

Responsibilities

• Own the most complex technical escalations from T1 and T2, serving as the final line of defense.
• Investigate and reproduce customer-reported bugs, data inconsistencies, and integration failures across Rewind's supported platforms (Jira, Confluence, GitHub, Shopify, QuickBooks Online, and more).
• Read and write code (primarily in the context of debugging and scripting) to diagnose issues, test hypotheses, and validate fixes.
• Work directly with Engineering to clearly articulate bugs, provide reproducible test cases, and track fixes through to resolution.
• Manage and resolve issues in customer environments involving API integrations, OAuth configurations, webhook failures, and platform-level permissions.
• Handle data restoration requests and complex recovery scenarios requiring deep knowledge of Rewind's backup architecture.
• Own enterprise customer onboarding when required, including installation, deployment, and education, ensuring the customer is fully set up for success.
• Help build and maintain the internal knowledge base for complex issue patterns, enabling T1/T2 to self-serve future resolutions.
• Participate in on-call rotations for P1 incidents affecting enterprise customers.
• Identify recurring escalation patterns and proactively surface product improvement opportunities to Engineering and Product.

Requirements

Required

• 5+ years of experience in a technical support, solutions engineering, or software development role.
• Computer Science degree or equivalent practical experience (you can read and write code).
• Proficiency in at least one scripting or programming language (Python, Ruby, JavaScript, or similar).
• Strong understanding of REST APIs, OAuth, webhooks, and modern SaaS integration patterns.
• Experience with cloud platforms and SaaS ecosystems (Atlassian, GitHub, Shopify, or similar).
• AWS - CloudWatch for logs, OpenSearch/Kibana for search infrastructure, SQS/SNS for async processing.
• Ability to read logs, inspect API responses, and debug issues at the network and application layers.
• Exceptional written and verbal communication - you can explain a complex technical root cause to a non-technical customer and to an engineer on the same day.
• Comfort working independently in ambiguous, high-stakes situations with limited documentation.

Nice to Have

• Experience with backup, recovery, or data resilience products.
• Familiarity with Jira, Confluence, or Atlassian platform administration.
• Experience with PostgreSQL and DynamoDB.
• Prior experience in a SaaS company at a similar scale (Series B / growth stage).
• Experience working with enterprise customers and navigating complex account relationships.

Location

There is a strong preference for candidates based in Ontario for easier collaboration.

Compensation

• Salary: CA$100K – CA$120K per year.
• Employment Type: Full-time, Remote.

We Offer

• 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
• $2000/year wellness/home office allowance
• $5000/year professional development allowance

About the Company

At Rewind, you’ll help shape the future of data protection for thousands of businesses. We’re performance-driven, innovative, and not afraid to challenge what’s possible. You’ll join a team that values trust, accountability, and respect for people’s time - and encourages every employee to experiment, think critically, and grow.

We support innovation through experimentation - including smart use of AI tools - and believe the best ideas come from those who aren’t afraid to push boundaries.

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.

AI Usage

Our recruitment process may include the use of artificial intelligence–enabled tools to help manage and review applications efficiently. These tools assist our team, but hiring decisions are ultimately made by human reviewers.