Sentry

More roles at Sentry

Senior Technical Support Engineer

Hybrid

Part remote, part office, you need to live within commuting distance of a named location.

Hybrid · Toronto, Ontario, Canada

Employer listed it 4 weeks ago · Added 4 weeks ago

Been open since 4 weeks ago, still being checked, but it has been live a while.

Salary

$125k to $150k per year

Location

Hybrid · Toronto, Ontario, Canada

Timezone

US East

Contract

Full-time

Experience

Senior

What the advert says

Quoted word for word from the employer's advert. Where it says nothing, we say so.

Working hours: Not mentioned in the advert
Where you can work from: Location eligibility not confirmed
Contract: 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.
Experience asked for: 5–8+ years of experience in technical support engineering, systems engineering, or software development, with a track record of solving high-complexity SaaS problems.
Pay: The base salary range (or hourly wage range, if applicable) that Sentry reasonably expects to pay for this position is $125,000 to $150,000.

Remote flexibility

Hybrid

This role is only partly remote, the employer expects time in the office around Toronto, Ontario, Canada, Hybrid, so you need to live within commuting distance.

What the employer says

Source listing states candidate location: "Toronto, Ontario, Canada, Hybrid"
Listing mentions "Hybrid"

What Nomaders makes of it

Not suitable if you plan to move between countries

The quotes above are the employer's own words; the reading is ours. Always check the original listing and employment terms before working from another country.

Before you apply

Questions worth asking: Nomaders interpretation

This role involves office time, but the advert does not say how often. Ask how many days a week are expected on site.

Produced automatically from this advert's text; not reviewed by a person. The employer's own page is the final word.

About the role

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

Requirements

·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.

Benefits

No benefits package published with this listing. Ask about it at first interview.

How to apply

1Check the flexibility label above, hybrid, matches where you plan to live and work.
2Tailor your CV to the role at Sentry, mentioning your remote working experience and working hours (US East).
3Apply directly on the employer's careers page using the button below. Nomaders never handles your application.

Found 27d ago. Last checked today. Always confirm the details on the original posting, salary and location can change after publication.

Listing sourced from Company boards.