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Senior Technical Support Engineer (T3)

Rewind - Toronto, ON, Canada - Hybrid - posted 2026-08-25

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Rewind is a cloud data protection platform that backs up critical business data from SaaS applications like Jira, GitHub, Confluence, and Shopify. The company is backed by Insight Partners, Inovia, Bessemer, and Atlassian Ventures, and was recognized as one of Canada's 50 fastest-growing technology companies in 2023. The Senior Technical Support Engineer (T3) role is the highest tier in Rewind's support organization, serving as the final escalation point for complex technical issues. This is a hybrid role that bridges customer support and engineering, requiring deep technical investigation and problem-solving. Key responsibilities include: - Owning the most complex technical escalations from T1 and T2 support teams - Investigating and reproducing customer-reported bugs, data inconsistencies, and integration failures across Rewind's supported platforms - Reading and writing code (primarily Python, Ruby, JavaScript) to diagnose root causes and validate fixes - Working directly with the Engineering team to articulate bugs, provide reproducible test cases, and track resolutions - Managing issues involving API integrations, OAuth configurations, webhook failures, and platform-level permissions - Handling data restoration requests and complex recovery scenarios using deep knowledge of Rewind's backup architecture - Owning enterprise customer onboarding, including installation, deployment, and education - Building and maintaining internal knowledge bases for complex issue patterns - Participating in on-call rotations for P1 incidents affecting enterprise customers - Identifying recurring escalation patterns and surfacing product improvement opportunities to Engineering and Product teams Required qualifications: - 5+ years in technical support, solutions engineering, or software development - Computer Science degree or equivalent practical experience - Proficiency in at least one scripting/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) - AWS experience (CloudWatch, OpenSearch/Kibana, SQS/SNS) - Ability to read logs, inspect API responses, and debug at network and application layers - Exceptional written and verbal communication skills - Comfort working independently in ambiguous, high-stakes situations Nice-to-have skills include experience with backup/recovery products, Atlassian platform administration, PostgreSQL, DynamoDB, and prior SaaS company experience at similar scale. The role requires participation in on-call rotations including weekends and holidays. Rewind values team-first mentality, performance-driven mindset, customer centricity, and taking initiative.

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