3 months ago
Toronto, CanadaSenior
Responsibilities
- Perform root-cause analysis on complex issues and distributed tracing gaps across polyglot environments
- Provide strategic technical consulting to senior engineers at enterprise customers on high-stakes architectural challenges
- Troubleshoot Sentry SDK implementations by examining source code and custom framework integrations
- Use support data and system signals to prioritize high-impact platform fixes with product teams
- Engineer deterministic support paths and automated resolution workflows for support agents
- Build knowledge context that enables consistent autonomous issue resolution
- Use MCP and Sentry internal APIs to develop agent skills for complex lookups and state checks
- Operate as the technical lead for agentic support operations across GitHub, Discord, and internal systems
Requirements
- 4+ years of experience in technical support engineering, systems engineering, or software development solving high-complexity SaaS problems
- Mastery of Python, JavaScript, Java, or Ruby and the ability to read SDK source code and identify production bugs
- Deep understanding of distributed systems, microservices, APIs, and end-to-end frontend-to-database behavior
- Practical familiarity with LLM orchestration, including RAG, context windows, and system prompts
- Ability to explain complex architectural concepts clearly and write precise system instructions for AI
- Active GitHub presence or experience maintaining open-source libraries is a bonus
- Prior full-time software development experience is a bonus
Benefits
- Eligible for employee benefit plans and programs applicable to the position
- Eligibility for incentive compensation and equity grants
- Paid time off
- Group health insurance coverage
Tech Stack
Categories
About Sentry
Sentry builds application monitoring and error/performance tracking tools for software developers, delivered as a SaaS with open-source SDKs and integrations. Teams use Sentry to detect, triage, and resolve production issues across web and mobile apps; the platform is used by 200,000+ organizations. Founded in 2011 and headquartered in San Francisco, Sentry is a privately held company.