Technical Support Engineer
Remote · Toronto, Ontario, Canada
Job Summary
Technical Support Engineer at Sentry focused on building an Autonomous Resolution Engine by fusing deep debugging with AI-driven automation. You will engage with elite developers across GitHub, Discord, and internal systems, serving as the Technical Lead for Agentic Operations, ensuring context-rich, human-in-the-loop resolution paths for complex architectural questions. Responsibilities include root-cause analysis across polyglot environments, guiding senior enterprise customers through high-stakes challenges, troubleshooting SDK implementations, and providing an engineering feedback loop to product teams. Core skills include mastery of Python, JavaScript, Java, or Ruby; deep understanding of distributed systems, APIs, microservices; familiarity with AI/LLM orchestration (RAG, context windows, system prompts); strong communication to explain architectures and write precise system instructions for AI; and a passion for automating repetitive work and building scalable observability and automation solutions.
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