[Hiring] Senior Technical Support Engineer @Rewind

Role Description

The Senior Technical Support Engineer (T3) is the highest tier of our support organization, serving as a bridge between customer support and engineering. You will own the most complex, ambiguous technical escalations that our T1 and T2 teams cannot resolve - including issues that previously required involvement from the Engineering Run Team.

As a Senior Technical Support Engineer, you will serve as the final escalation point within the support organization. You bring a software development background and deep technical instincts to diagnose root causes, reproduce edge cases, write or read code to understand issues at depth, and work directly with the Engineering team to drive resolution. This is not a traditional support role - you will spend a significant portion of your time doing technical investigation work that sits at the boundary of support and engineering.

This role requires participation on a on-call rotation including weekends and holidays.

What You'll Do

• 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.

Qualifications

• 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 Philosophy

The actual base salary will vary based on various factors, including market and individual qualifications objectively assessed during the interview process. The listed range above is a guideline, and the base salary range for this role may be modified.

If your expectations are above this range, it may be because your experience aligns with a more senior level. In some cases, we’re open to hiring at a higher level for the right person and are committed to paying competitively and fairly.

If your experience is closer to an earlier career stage, we may still consider your application. In that case, we would evaluate the role at a different level within our levelling framework, which would correspond to a salary below the range shown.

Pay is just one part of the overall compensation at Rewind.

Benefits

• 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.

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.