Senior Technical Support Engineer

at Sentry

📍 Toronto, Canada

USD 125,000-150,000 per year

SENIOR

✅ Hybrid

Tech Stack
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.

AI @ 9 API @ 7 Agentic Systems CI/CD @ 6 Communication @ 9 Distributed Systems @ 7 GitHub @ 1 Java @ 7 JavaScript @ 7 LLM @ 3 Microservices @ 7 Observability Python @ 7 RAG @ 3 React @ 6 Ruby @ 7 Sentry Software Development @ 7

Details

Sentry helps developers fix errors and performance issues before users notice. The Support team treats technical support as an engineering discipline and is building an autonomous resolution engine that combines human expertise with agentic systems.

Responsibilities

Support Developers and Solve Complex Technical Issues

Perform root-cause analysis on complex issues and distributed tracing gaps across polyglot environments.
Act as a strategic consultant for senior engineers at enterprise customers, solving high-stakes architectural challenges related to observability.
Troubleshoot Sentry SDK implementations by examining source code and helping developers instrument complex frameworks and custom environments.
Serve as a bridge between developers and product teams, using support data to prioritize high-impact platform fixes.

Engineer Agentic Operations

Engineer deterministic support paths that enable high-fidelity, autonomous resolutions.
Build knowledge and context into support systems so they can resolve issues consistently.
Use MCP (Model Context Protocol) and Sentry’s internal APIs to build agent skills for complex lookups and state checks.
Apply the Seer philosophy of autonomous production fixes to the support lifecycle.
Engage with users through GitHub, Discord, and internal systems while providing a human-in-the-loop path for complex issues.

Requirements

5–8+ years of experience in technical support engineering, systems engineering, or software development, with experience solving complex SaaS problems.
Strong coding foundations in Python, JavaScript, Java, or Ruby.
Ability to read SDK source code and identify bugs in production-level repositories.
Deep understanding of distributed systems, microservices, APIs, and the path from frontend to database.
Practical familiarity with LLM orchestration, including RAG, context windows, and system prompts.
Ability to assess where AI succeeds and where human intervention is required.
Exceptional communication skills, including explaining complex architectural concepts and writing precise system instructions for AI.
Ability to troubleshoot across React frontends, Python backends, and CI/CD pipelines.
An active GitHub presence or experience maintaining open-source libraries is a bonus.
Full-time software development experience is a bonus.

Benefits

Eligible candidates may participate in applicable employee benefit plans and programs, including incentive compensation, equity grants, paid time off, and group health insurance coverage.
Sentry is committed to equal employment opportunity and provides reasonable accommodations for candidates and employees with disabilities.