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Technical Support Engineer

Sentry· Support
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Hybrid (Toronto, Ontario, Canada)CA$100k - CA$125kFull-timePosted 3mo ago

About the role

Sentry is seeking a Technical Support Engineer to architect and operationalize a scalable support engine, combining deep debugging with autonomous agentic systems to provide high-impact, automated resolutions for complex SaaS issues in a hybrid, Toronto-based role.

Responsibilities

  • Deep-Dive Debugging: Perform root-cause analysis on complex issues and distributed tracing gaps across polyglot environments.
  • Support the Great Minds: Act as a strategic consultant for senior engineers at enterprise customers, solving high-stakes architectural challenges.
  • Troubleshoot SDK Implementations: Dive into Sentry SDK source code to help instrument complex frameworks and custom environments.
  • Engineering Feedback Loop: Bridge developers and product teams using data from systems to prioritize platform fixes.
  • Engineer Agentic Operations (The Scaling Engine): Determine deterministic support paths, build context into systems, and develop agentic tooling using MCP and internal APIs.
  • Apply the Seer philosophy to support lifecycle, moving from a Help Desk to Autonomous Resolution Engine.

Qualifications

  • 4+ years of experience in technical support engineering, systems engineering, or software development, with a track record of solving high-complexity SaaS problems.
  • Mastery of Python, JavaScript, Java, or Ruby; comfortable reading SDK source code and identifying bugs in production-level repositories.
  • Deep understanding of distributed systems, microservices, APIs, and frontend-to-database workflows.
  • Practical familiarity with LLM orchestration (RAG, context windows, system prompts) and discerning where AI can help vs. where human input is required.
  • Exceptional communication: ability to explain complex architectural concepts and write precise system instructions for AI.

Skills

Required:Root-cause analysisSDK analysisDistributed systems
Nice to have:LLM orchestration

Benefits

  • See Sentry Benefits for details (incl. incentive compensation, equity grants, paid time off, group health insurance).
  • Employee benefit plans/programs applicable to the position; eligibility for equity and benefits.
Last updated Aug 16, 2026. Interested? Apply on the company site.
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About Sentry

Application Performance Monitoring & Error Tracking Software

Application performance monitoring for developers & software teams to see errors clearer, solve issues faster & continue learning continuously. Get started at sentry.io.

AI code reviewAI/SeerApplication MonitoringCode breaksCode breaks,Error TrackingLogsMCP server
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