Senior Technical Support Engineer

Posted 3 days ago

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About the role

  • Senior Technical Support Engineer helping Sentry, an application monitoring platform, debug complex SaaS issues. Building MCP-powered agentic support systems and autonomous resolution paths.

Responsibilities

  • Perform root-cause analysis on complex issues and distributed tracing gaps across polyglot environments
  • Act as a strategic consultant for senior engineers at enterprise customers
  • Solve high-stakes architectural challenges related to observability
  • Troubleshoot Sentry SDK implementations by reading source code and investigating complex frameworks and custom environments
  • Bridge customer feedback and product teams to prioritize high-impact platform fixes
  • Engineer deterministic logic for support agents and autonomous resolutions
  • Build knowledge context into support systems
  • Develop agentic tooling and skills using MCP and Sentry internal APIs
  • Engage users across GitHub, Discord, and internal systems
  • Act as Technical Lead for Agentic Operations
  • Create human-in-the-loop escalation paths for complex support issues
  • Help evolve support from a help desk into an autonomous resolution engine

Requirements

  • 5–8+ years of experience in technical support engineering, systems engineering, or software development
  • 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 the path from frontend to database
  • Practical familiarity with LLM orchestration, including RAG, context windows, and system prompts
  • Ability to identify where AI succeeds and where human intervention is required
  • Ability to explain complex architectural concepts to humans
  • Ability to write precise system instructions for AI
  • Active GitHub presence or experience maintaining open-source libraries (bonus qualification)
  • Full-time software development experience (bonus qualification)
  • Willingness to work in Sentry’s Toronto office on Mondays, Tuesdays, and Thursdays
  • Must answer whether visa sponsorship will be required to work in Canada

Benefits

  • Incentive compensation
  • Equity grants
  • Paid time off
  • Group health insurance coverage
  • Reasonable accommodations for employees and candidates with disabilities
  • Inclusive culture and equal employment opportunities

Job type

Full Time

Experience level

Senior

Salary

$125,000 - $150,000 per year

Degree requirement

No Education Requirement

Tech skills

Distributed SystemsJavaJavaScriptMicroservicesPythonRuby

Location requirements

HybridTorontoCanada

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