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Senior Technical Support Engineer

Sentry· Support
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Hybrid (Toronto, Ontario, Canada)$125k - $150kFull-timePosted 3w ago

About the role

Senior Technical Support Engineer at Sentry, a role focused on architecting the Technical Support engine by combining deep human expertise with autonomous agentic systems. You will act as a debugger of code and systems, orchestrating support across channels and providing deep technical guidance to enterprise customers while building automated resolution paths and a human-in-the-loop workflow.

Responsibilities

  • Master the Sentry Ecosystem & Support Elite Developers
  • 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 our largest enterprise customers, solving high-stakes architectural challenges that push the boundaries of observability.
  • Troubleshoot SDK Implementations: Go deep into the source code of Sentry’s SDKs to help developers instrument complex frameworks and custom environments.
  • Engineering Feedback Loop: Serve as the bridge between the world's best developers and our product teams, using data from your systems to prioritize high-impact platform fixes.
  • Engineer Agentic Operations (The Scaling Engine)
  • Deterministic Support Paths: Engineer the logic that powers our support agents, moving beyond probabilistic guesses to high-fidelity, autonomous resolutions.
  • Knowledge Engineering: Build the right context into our systems so they can resolve issues consistently and indefinitely.
  • Agentic Tooling Development: Use MCP (Model Context Protocol) and Sentry’s internal APIs to build "skills" for our agents, allowing them to perform complex lookups or state-checks autonomously.
  • The Seer Philosophy: Apply autonomous production fixes philosophy to the support lifecycle, moving from a "Help Desk" to an "Autonomous Resolution Engine."

Qualifications

  • 5–8+ years of experience in technical support engineering, systems engineering, or software development, with a track record of solving high-complexity SaaS problems.
  • Strong Coding Foundations: Mastery of Python, JavaScript, Java, or Ruby. Comfortable reading SDK source code and identifying bugs in production-level repositories.
  • Systems Depth: Deep understanding of distributed systems, microservices, APIs, and the "path of a pixel" from frontend to database.
  • AI & Automation Literacy: Practical familiarity with LLM orchestration (RAG, context windows, system prompts) and a critical eye for where AI succeeds versus where it requires human intervention.
  • Exceptional Communication: The ability to explain complex architectural concepts to a human and write precise "system instructions" for an AI.
  • Bonus qualifications: Open Source Contributor; Former Software Developer

Skills

Required:PythonJavaScript
Nice to have:JavaRuby

Benefits

  • See [Sentry Benefits](https://sentry.io/careers/) for more details about the Company’s benefit plans/programs.
Last updated Oct 4, 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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