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
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