Technical Support Engineer

Location: Toronto, Ontario, Canada Workplace: Hybrid ABOUT SENTRY Software runs the world and the pace is faster than ever. Sentry helps developers fix errors and performance issues before users notice, so teams can spend less time firefighting and more time building. Trusted by 200,000+ organizations, Sentry is today’s application monitoring standard and our team is building its AI-native future. ABOUT THE ROLE 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. IN THIS ROLE YOU WILL Master the Sentry Ecosystem & Support Elite Developers - Deep-Dive Debugging: Perform root-cause analysis on complex issues and distributed tracing gaps across polyglot environments. - Support the Great 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." YOU’LL LOVE THIS JOB IF - 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. QUALIFICATIONS - 4+ 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. BONUS QUALIFICATIONS - 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. The base salary range (or hourly wage range, if applicable) that Sentry reasonably expects to pay for this position is $100,000 to $125,000 CAD. A successful candidate’s actual base salary (or hourly wage) amount will be determined by a variety of relevant factors including, without limitation, the candidate’s work location, education, work and other relevant experience, skills, and job-related knowledge. A successful candidate will be eligible to participate in Sentry’s employee benefit plans/programs applicable to the candidate’s position (including incentive compensation, equity grants, paid time off, and group health insurance coverage). See Sentry Benefits https://sentry.io/careers/ for more details about the Company’s benefit plans/programs. EQUAL OPPORTUNITY AT SENTRY Sentry is committed to providing equal employment opportunities to its employees and candidates for employment regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity, veteran status, or other legally-protected characteristic. This commitment includes the provision of reasonable accommodations to employees and candidates for employment with physical or mental disabilities who require such accommodations in order to (a) perform the essential functions of their jobs, or (b) seek employment with Sentry. We strive to build a diverse team, with an inclusive culture where every teammate can thrive. Sentry is an open-source company because we believe that everyone, everywhere, should have the ability and tools to make great software. Software should be accessible. That starts with making our industry accessible. If you need assistance or an accommodation due to a disability, you may contact us at accommodations@sentry.io. Want to learn more about how Sentry handles applicant data? Get the details in our Applicant Privacy Policy https://sentry.io/careers/applicantprivacy/.