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Added 3 months ago
EN
Distinguished SW Systems Engineer (10343)
Extreme Networks
Toronto, ON
- Full-time
Added 29 days ago
Senior Data Software Engineer
Scotiabank
Toronto, ON
Strong programming skills (Python and/or Java)
Added 3 months ago
CI
Software Developer in Test (Contract) -
CoreFactor Inc.
North York, Ontario
- Contract
CoreFactor is searching for a Software Developer in Test (SDET) on a contract basis for a client in the GTA.
Added 3 months ago
IL
Advanced Engineer, Product Engagement
Invesco Ltd.
Charlottetown, Prince Edward Island
- Full-time
Expertise in MuleSoft 4, API led connectivity, Microservices, Java
Added 4 months ago
M
Principal Software Engineer - Distributed Systems
Microsoft
Vancouver, British Columbia
- Full-time
…coding in languages including, but not limited to, C, C++, C#, Java, JavaScript, or…
Added 3 months ago
S
Technical Support Engineer
Sentry
Remote, Canada
- $100,000 to $125,000 CAD / year
- Full-time
- Remote
…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,…
Added 3 months ago
B
Senior Java Data Engineering Developer
Bounteous
Montreal, Quebec
- Full-time
Develop and maintain Java-based backend and data processing components
Added 3 months ago
C
Apps Development Sr Manager - Vice President
Citi
Remote, Canada
- Full-time
- Remote
Strong exposure to Java, Spring Framework, Spring Boot, Kafka, MQ, Micro-Service , Oracle, Mongo, Openshift, REST, Maven, Git, JUnit, TDD, Agile, Strong knowledge on CI CD pipeline and…
Added 3 months ago
IL
Advanced Quality Engineer
Invesco Ltd.
Charlottetown, Prince Edward Island
- Full-time
Demonstrated experience with test automation frameworks and scripting languages (Python, JavaScript, Java, etc.).
Added 1 month ago
Senior Manager, Data Engineering
Scotiabank
Toronto, ON
Added 3 months ago
R&
Senior IT Recruitment Consultant - VMS
Robertson & Company
Toronto, Ontario
- Full-time
Apply knowledge of programming languages (Java, Python, .NET, SQL, etc.) to effectively assess candidates
Added 3 months ago
Applied Scientist, Alexa Smart Home
Amazon
Vancouver, British Columbia
- Experience programming in Java, C++, Python or related language
Added 1 month ago
GM
Senior Software Developer - Test Automation
General Motors
Remote, Canada
- Full-time
- Remote
Strong programming skills in Python, other languages such as Java, C#, or JavaScript are a bonus.
Added 1 month ago
Associate Platform Engineer
Scotiabank
Toronto, ON
…operations that leverage such technologies as React, Node JS,Java 8, RESTful services,…
Added 3 months ago
C
Apps Dev Tech Lead Analyst - Vice President
Citi
Remote, Canada
- Full-time
- Remote
Design, develop, and maintain high-quality Java applications using Spring Boot, microservices architecture, and Angular/React FE.
Added 3 months ago
AT
Principal Software Developer
Aspen Technology
Montreal, Quebec
- Full-time
AspenTech is looking for a talented and experienced Developer with Quality background to join our Enterprise Operations Platform (EOP) organization. In this role, you will be responsible…
Added 2 months ago
CO
Staff Software Engineer - Capital One Travel - Android
Capital One
Toronto, Ontario
- Full-time
At least 6 years of hands-on development of Native Android applications using Java/Kotlin
Added 4 months ago
TA
Senior Software Engineer
Treasure AI
Vancouver, BC
- $132,500 to $171,000 CAD / year
- Full-time
Strong backend proficiency (experience with Ruby, Go, Java, or Kotlin is preferred), including a solid understanding of database design and API scalability.
Added 1 month ago
EM
Senior Software Engineer - Backend
Evertz Microsystems Limited
Burlington, ON
- Full-time
5+ years of software engineering experience in a strongly typed language; Java preferred (Python, Rust, Go, C++, or C# also considered)
Added 24 days ago
RR
Principal Android Engineer
Rakuten Rewards
Toronto, ON · CN-Yonge Sheppard Center
- Full-time
…including generative AI and intelligent automation, to enhance developer productivity, optimize application capabilities, and drive innovation in mobile platform…
Added 4 months ago
EI
Full-Stack Software Developer
Engineered Intelligence Inc.
Mississauga, Ontario
- Full-time
The Position: Do our values align with you? Are you an experienced Full-Stack Software Developer looking to join a dedicated team working together to build rewarding careers and an…
Added 4 months ago
B
Full Stack Developer, Tax Transformation Office
BDO
Toronto, Ontario
- Full-time
We are seeking an exceptionally skilled Full Stack Developer to join the Tax R&D Lab within the Tax Transformation Office and help build the next generation of intelligent platforms,…
Added 4 months ago
B
Applied AI Engineer
Bounteous
Montreal, Quebec
- Full-time
5+ years of strong front-to-back engineering experience, focusing on AI ML platforms and workflows (Python or Java).
Added 1 month ago
Developer, Cloud Engineering
Scotiabank
Toronto, ON
Breadth of technology and language experience, excellent coding practices (Microservices, Event Streaming, Databases, Cryptography, Kubernetes, Java Spring Boot, Python, Helm, HCL)
Added 4 months ago
S
Information Security Operations Analyst (Toronto, Canada)
Starling
Remote, Canada
- Full-time
- Remote
Any experience of programming in Python, Go and/or Java.

Sentry

Technical Support Engineer

Remote, Canada

Remote

$100,000 to $125,000 CAD / year · Full-time

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Job details

Pay: $100,000 to $125,000 CAD / year
Job type: Full-time
Workplace: Remote
Experience: 4+ years of experience in technical support engineering, systems engineering, or software development, with a track record of solving high-complexity SaaS problems.
Posting language: English
Posted: Jun 10, 2026

Original job description

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

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. 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.

Bonus qualifications

Open Source Contributor: An active presence on GitHub or experience maintaining open-source libraries.
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.

The base salary range (or hourly wage range, if applicable) that Sentry reasonably expects to pay for this position is $100,000 to $125,000 CAD. A successful candidate’s actual base salary (or hourly wage) amount will be determined by a variety of relevant factors including, without limitation, the candidate’s work location, education, work and other relevant experience, skills, and job-related knowledge. A successful candidate will be eligible to participate in Sentry’s employee benefit plans/programs applicable to the candidate’s position (including incentive compensation, equity grants, paid time off, and group health insurance coverage). See Sentry Benefits for more details about the Company’s benefit plans/programs.

Equal Opportunity at Sentry

Sentry is committed to providing equal employment opportunities to its employees and candidates for employment regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity, veteran status, or other legally-protected characteristic. This commitment includes the provision of reasonable accommodations to employees and candidates for employment with physical or mental disabilities who require such accommodations in order to (a) perform the essential functions of their jobs, or (b) seek employment with Sentry. We strive to build a diverse team, with an inclusive culture where every teammate can thrive. Sentry is an open-source company because we believe that everyone, everywhere, should have the ability and tools to make great software. Software should be accessible. That starts with making our industry accessible.

If you need assistance or an accommodation due to a disability, you may contact us at accommodations@sentry.io.

Want to learn more about how Sentry handles applicant data? Get the details in our Applicant Privacy Policy.

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More about this job

Responsibilities

The role involves performing deep-dive debugging and root-cause analysis for elite developers while acting as a strategic consultant for enterprise customers. Additionally, the engineer will build autonomous agentic systems and deterministic support paths to scale technical resolution.

Requirements

Requires 4+ years of experience in technical support or software development with mastery of languages like Python, JavaScript, Java, or Ruby. Candidates must have a deep understanding of distributed systems and practical familiarity with LLM orchestration and AI automation.

Skills

Python
JavaScript
Java
Ruby
Distributed Systems
Microservices
API Troubleshooting
LLM Orchestration
RAG
Root Cause Analysis
SDK Implementation
CI/CD Pipelines
React
Model Context Protocol
Technical Support Engineering
Knowledge Engineering

Benefits

Incentive Compensation
Equity Grants
Paid Time Off
Group Health Insurance Coverage

Visa sponsorship

Not detected in the job text

Keywords

Sentry
Observability
Distributed Tracing
Polyglot Environments
Agentic Ops
Human-in-the-Loop
MCP
Model Context Protocol
SaaS
Open Source
GitHub
Discord
RAG
System Prompts
Context Windows
Full-Stack Troubleshooting
Developer Advocacy
Technical Lead
Autonomous Resolution Engine
API
Microservices
Python
JavaScript
Java
Ruby
React
CI/CD
SDK
Root Cause Analysis
Knowledge Engineering

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