Who you are

- You love eliminating Non-scalable effort: you enjoy automating repetitive work and take pride in building systems that save time and effort

- You’re a Full-Stack Troubleshooter: You enjoy jumping from a React frontend issue to a Python backend trace to a CI/CD pipeline failure in a single afternoon

- You Value Evidence-Based Support: You prefer looking at data trends over anecdotal evidence to decide where to build automation next

- You’re a Developer Advocate: You want to guide the industry on how elite engineers and AI co-exist in a high-density technical ecosystem

- 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. You are 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

- Open Source Contributor: An active presence on GitHub or experience maintaining open-source libraries

- Former Software Developer: You’ve spent time in the trenches as a full-time dev and know exactly what keeps our customers up at night





What the job involves

- At Sentry, Support is an engineering discipline. Our customers are the greatest technical minds in the world—developers at elite enterprises building the future of software—and they deserve answers that go deeper than a knowledge base link

- We are architecting the Technical Support engine. We’re looking for a veteran engineer to help us redefine the standard of technical support by combining deep human expertise with autonomous agentic systems. You are a debugger of both code and systems. You will treat support volume as a data signal to build automated resolution paths, ensuring our human engineers only touch the most complex, high-impact architectural puzzles

- Sentry Support Engineers aren't just clearing queues; they are Orchestrators. You will engage with our users across GitHub, Discord, and our internal systems, while acting as the Technical Lead for our Agentic Ops. You ensure that when a developer asks a complex question, our systems have the right context and a seamless "Human-in-the-Loop" path to you when deep, nuanced expertise is required

- Deep-Dive Debugging: Perform root-cause analysis on complex issues and distributed tracing gaps across polyglot environments





- Support the Excellent 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: We’ve already proven AI can handle autonomous production fixes with Seer. You will apply that same philosophy to the support lifecycle—moving us from a "Help Desk" to an "Autonomous Resolution Engine."

Benefits

- Competitive Compensation + Equity
- 401k Plan

- Medical, Dental, Vision Insurance

- Commuter Stipend

- Professional Development Stipend
- Health & Wellness Benefits

- Charitable Matching Program

- Flexible PTO

- Paid Parental Leave

📌 Senior Technical Support Engineer (Toronto)
🏢 Sentry
📍 Toronto