Used Tools & Technologies
Not specified
Required Skills & Competences
Tag name is followed by "@" symbol and proficiency level value.
About proficiency levels:
- 1-2 — basic awareness. Minimal hands-on experience, and a rudimentary understanding of the technology's purpose;
- 3-6 — daily use. Comfortable and regular usage, capable of handling common tasks and challenges related to the technology;
- 7-9 — you are an expert, you can teach others, you know all the pitfalls and tricks;
- 10 — exceptional knowledge, comprehensive understanding, and adeptness in all aspects of the technology, including advanced problem-solving. Think twice before claiming or demanding such level.
Software Development @ 5
Ruby @ 6
Python @ 3
Java @ 6
GitHub @ 3
CI/CD @ 3
Distributed Systems @ 6
Communication @ 3
JavaScript @ 6
React @ 3
Microservices @ 6
API @ 3
LLM @ 2
Sentry @ 3
Observability @ 3
AI @ 3
RAG @ 2
- 1-2 — basic awareness. Minimal hands-on experience, and a rudimentary understanding of the technology's purpose;
- 3-6 — daily use. Comfortable and regular usage, capable of handling common tasks and challenges related to the technology;
- 7-9 — you are an expert, you can teach others, you know all the pitfalls and tricks;
- 10 — exceptional knowledge, comprehensive understanding, and adeptness in all aspects of the technology, including advanced problem-solving. Think twice before claiming or demanding such level.
Details
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 building its AI-native future.
About the Role
At Sentry, Support is treated as an engineering discipline. This role is focused on architecting the Technical Support engine: combining deep human expertise with autonomous, agentic systems. You will act as a debugger of both code and systems, treating support volume as a data signal to build automated resolution paths so human engineers only handle the most complex, high-impact problems. You will engage with users across GitHub, Discord, and internal systems, and act as the Technical Lead for Agentic Ops to ensure seamless human-in-the-loop escalation when needed.
Responsibilities
- Master the Sentry ecosystem and support elite developers:
- Perform root-cause analysis on complex issues and distributed tracing gaps across polyglot environments.
- Act as a strategic consultant for senior engineers at large enterprise customers to solve architectural observability challenges.
- Troubleshoot SDK implementations and dive into Sentry SDK source code to help instrument complex frameworks and custom environments.
- Bridge customers and product teams by using data from support systems to prioritize platform fixes.
- Engineer Agentic Operations (the scaling engine):
- Design deterministic support paths that power support agents for high-fidelity autonomous resolutions.
- Perform knowledge engineering to embed the right context into systems for consistent automated resolution.
- Build agentic tooling using MCP (Model Context Protocol) and Sentry internal APIs to provide agent "skills" for complex lookups and state checks.
- Apply the Seer philosophy (autonomous production fixes) to the support lifecycle to move from a help desk to an autonomous resolution engine.
You’ll love this job if
- You enjoy eliminating non-scalable effort and building systems that automate repetitive work.
- You are a full-stack troubleshooter who can jump from React frontend issues to Python backend traces to CI/CD pipeline failures.
- You value evidence-based support and use data trends to decide where to build automation next.
- You want to be a developer advocate guiding how elite engineers and AI coexist in high-density technical ecosystems.
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; comfortable reading SDK source code and identifying bugs in production repositories.
- Deep understanding of distributed systems, microservices, APIs, and the full stack from frontend to database.
- Practical familiarity with LLM orchestration (RAG, context windows, system prompts) and the ability to judge when AI requires human intervention.
- Exceptional communication skills: explain complex architectural concepts and write precise system instructions for AI.
Bonus Qualifications
- Open source contributor or active presence on GitHub.
- Former software developer experience.
Compensation & Benefits
The base salary range Sentry reasonably expects to pay for this position is CA$100,000 to CA$125,000. A successful candidate’s actual base salary will be determined by factors including work location, experience, skills, and job-related knowledge. A successful candidate will be eligible to participate in Sentry’s employee benefit plans/programs applicable to the position, including incentive compensation, equity grants, paid time off, and group health insurance coverage.
Equal Opportunity & Accommodations
Sentry is committed to providing equal employment opportunities and reasonable accommodations to applicants and employees with disabilities. If you need assistance or an accommodation due to a disability, contact [email protected].