Senior Technical Support Engineer — Escalations & Eng

Rewind; Ontario (CA); On-site; USD 79,000 - 115,000; Full time

Benefits offered by this job

Flexible work hours

Employee stock options

Health benefits

3 weeks vacation

Wellness allowance

Professional development allowance

Volunteer day

Job summary

Rewind is seeking a Senior Technical Support Engineer (T3) based in Ontario to own the most complex technical escalations at the intersection of support and engineering. You will diagnose root causes, read/write code, and drive resolution with the Engineering team, including on-call rotations and enterprise onboarding.

You’ll work across platforms like Jira, Confluence, GitHub, Shopify, and others, leveraging your CS background and scripting skills to debug and validate fixes.

Qualifications

• 5+ years in a technical support, solutions engineering, or software development role.
• Computer Science degree or equivalent practical experience.
• 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 across network and application layers
• Exceptional written and verbal communication to explain complex root causes to non-technical customers and engineers
• Comfort working independently in ambiguous, high-stakes situations with limited documentation

Responsibilities

• Own the most complex technical escalations from T1 and T2; final line of defense.
• Investigate and reproduce customer-reported bugs, data inconsistencies, and integration failures across supported platforms (Jira, Confluence, GitHub, Shopify, QuickBooks Online, and more).
• Read and write code to diagnose issues, test hypotheses, and validate fixes.
• Collaborate with Engineering to articulate bugs and track fixes to resolution.
• Manage and resolve issues in customer environments involving API integrations and platform-level permissions.
• Handle data restoration requests and complex recovery scenarios requiring deep backup architecture knowledge.
• Own enterprise customer onboarding including installation and education for success.
• Help build internal knowledge base for complex issue patterns.
• Participate in on-call rotations for P1 incidents affecting enterprise customers.
• Identify recurring escalation patterns and surface product improvement opportunities to Engineering and Product.

Skills

Python

REST APIs

OAuth

Webhooks

SaaS integration

AWS CloudWatch

OpenSearch/Kibana

PostgreSQL

Jira/Confluence/Atlassian

GitHub

Communication

Education

Computer Science degree

Tools

Jira

Confluence

GitHub

Shopify

OpenSearch

Job description

Rewind is seeking a Senior Technical Support Engineer (T3) based in Ontario to own the most complex technical escalations at the intersection of support and engineering. You will diagnose root causes, read/write code, and drive resolution with the Engineering team, including on-call rotations and enterprise onboarding.

You’ll work across platforms like Jira, Confluence, GitHub, Shopify, and others, leveraging your CS background and scripting skills to debug and validate fixes.