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Technical Support Engineer

SentryToronto, Ontario, CanadaSupport
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Salary
$100K - $125K CAD
Job type
Full-time
Work mode
Remote
Posted
10 Jun 2026
Status
Open · checked 7d ago

About this role

Role Overview

The Technical Support Engineer role at Sentry in Toronto offers a full-time, remote-friendly opportunity for a veteran engineer to shape the future of support infrastructure. This position suits a skilled debugger who wants to combine human expertise with autonomous agentic systems to assist elite software developers.

Key Responsibilities

Perform root-cause analysis on intricate issues and distributed tracing gaps across polyglot environments.
Act as a strategic consultant for senior engineers at major enterprise organizations to resolve high-stakes architectural challenges.
Inspect the source code of Sentry's SDKs to assist developers in instrumenting complex frameworks and custom setups.
Use support volume data as a signal to prioritize high-impact platform fixes with product teams.
Engineer deterministic support paths and build context into systems for autonomous issue resolution.
Develop agentic tooling using Model Context Protocol and internal APIs to create specialized skills for support agents.

Requirements

Minimum of 4 years of professional experience in technical support engineering, software development, or systems engineering, dealing with high-complexity SaaS problems.
Strong coding foundations with mastery in Python, JavaScript, Java, or Ruby, enabling the reading of SDK source code and production-level bug identification.
Deep familiarity with distributed systems, microservices, APIs, and end-to-end data flow.
Practical knowledge of LLM orchestration, including RAG, context windows, and system prompts, alongside a clear understanding of human-in-the-loop boundaries.
Excellent communication skills capable of explaining advanced architectural ideas to humans and writing precise instructions for AI systems.

Nice to Have

Active presence on GitHub or experience as an open-source contributor maintaining public libraries.
Background as a former full-time software developer with firsthand knowledge of customer challenges.

Skills and Tools

Python
React
JavaScript
Java
LLM
RAG
Distributed Systems and Microservices
APIs and SDK Source Code

Salary and Benefits

Base salary range of $100,000 to $125,000 CAD per year, with actual compensation determined by location, education, experience, and skills.
Eligibility to participate in company benefit plans including incentive compensation, equity grants, paid time off, and group health insurance.

About the Company

Sentry builds the application monitoring standard trusted by over 200,000 organizations to help developers find and fix errors and performance issues before users notice. The company operates with an open-source philosophy, aiming to make software and the tech industry accessible to everyone everywhere.

How to Apply

Visit the official company careers page to submit an application for this position.

Skills and tech stack

PythonReactJavaScriptJavaLLMRAG

Questions candidates ask

What is the salary range for this role?

The base salary range is $100,000 to $125,000 CAD per year, with final compensation dependent on factors like location, education, experience, and skills.

Where is the job located?

The position is based in Toronto, Ontario, Canada, with remote work options available.

How many years of experience are required?

Candidates must have at least 4 years of experience in technical support engineering, software development, or systems engineering.

What technical skills are needed?

Required skills include programming in Python, JavaScript, Java, or Ruby, familiarity with React, understanding of distributed systems, and practical experience with LLMs and RAG.

What benefits are included?

Successful candidates are eligible for incentive compensation, equity grants, paid time off, and group health insurance coverage.

Ready to apply?

The application is on the official Sentry careers page.

Apply on company site