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Senior Technical Support Engineer

SentryToronto, Ontario, CanadaSupport
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Salary
$125K - $150K USD
Job type
Full-time
Work mode
Remote
Posted
30 Sept 2026
Status
Open · checked 7d ago

About this role

Sentry is seeking a Senior Technical Support Engineer to join the team in Toronto, Ontario, Canada, with a remote work arrangement. This full-time role suits a veteran engineer who wants to blend advanced software troubleshooting with autonomous agentic systems.

Role Overview

At Sentry, support is treated as an engineering discipline where the customer base consists of elite software developers. This position goes beyond traditional help desk tasks by combining deep human expertise with automated agentic workflows. The professional in this role will act as an orchestrator, handling complex architectural challenges while engineering autonomous resolution paths to scale support operations efficiently.

Key Responsibilities

Conduct deep-dive debugging and root-cause analysis on distributed tracing gaps across polyglot environments.
Act as a strategic consultant for senior engineers at major enterprise accounts, resolving high-stakes observability challenges.
Review the source code of Sentry SDKs to assist developers in instrumenting complex frameworks and custom environments.
Serve as a critical feedback bridge between users and product teams to prioritize high-impact platform fixes using support data.
Engineer deterministic support paths and build context for autonomous support agents using internal APIs and Model Context Protocol.
Engage users across GitHub, Discord, and internal channels while managing human-in-the-loop escalation paths.

Requirements

Possess 5 to 8+ years of professional background in technical support engineering, systems engineering, or software development.
Demonstrate strong coding foundations with mastery in Python, JavaScript, Java, or Ruby, alongside the ability to read SDK source code.
Bring a deep understanding of microservices, distributed systems, APIs, and end-to-end data flows.
Display practical familiarity with AI and automation literacy, including LLM orchestration, RAG, context windows, and system prompts.
Exhibit exceptional communication skills to explain intricate architectural concepts to humans and write precise instructions for AI systems.

Nice to Have

Active open-source contributor with a presence on GitHub or experience maintaining open-source libraries.
Prior professional background working full-time as a software developer.

Skills and Tools

Python
React
JavaScript
Java
LLM
RAG
Model Context Protocol (MCP)
Distributed systems and microservices

Salary and Benefits

The base salary range for this position is $125,000 to $150,000 USD per year. Actual compensation is determined by factors such as work location, education, relevant experience, skills, and job-related knowledge. Eligible candidates may also participate in company benefit programs including incentive compensation, equity grants, paid time off, and group health insurance coverage.

About the Company

Sentry builds application monitoring solutions trusted by over 200,000 organizations to help developers fix errors and performance issues proactively. The company operates with a commitment to equal employment opportunities, fostering an inclusive culture, and maintaining an open-source philosophy that aims to make software accessible to everyone, everywhere.

How to Apply

Candidates interested in this opportunity should visit the official Sentry careers page to submit an application.

Skills and tech stack

PythonReactJavaScriptJavaLLMRAG

Questions candidates ask

What is the location and work setup for this role?

The position is based in Toronto, Ontario, Canada, and features a remote work option.

What is the salary range for the Senior Technical Support Engineer?

The base salary range spans from $125,000 to $150,000 USD per year, depending on factors such as location, education, and relevant experience.

How many years of experience are required?

The role requires 5 to 8+ years of experience in technical support engineering, software development, or systems engineering.

What programming languages are required for this position?

Candidates need strong coding foundations and mastery in languages such as Python, JavaScript, Java, or Ruby.

How do I apply for this job?

Interested applicants should apply directly through the official Sentry careers website.

Ready to apply?

The application is on the official Sentry careers page.

Apply on company site