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Added 4 months ago
S
Technical Support Engineer
Sentry
Remote, Canada
- $100,000 to $125,000 CAD / year
- Full-time
- Remote
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…
Added 4 months ago
KC
Forward Deployed AI Engineer
Keyrus Canada
Toronto, ON · Montreal, QC
- Full-time
We are currently building our talent pipeline for upcoming Forward Deployed AI Engineer opportunities in Canada. While we may not have an immediate opening today, we are actively connecting…
Added 4 months ago
C
Apps Development Sr Manager - Vice President
Citi
Mississauga, Ontario
- Full-time
Collaborate with development teams to create a seamless developer experience and ensure applications are built with scalability, reliability, and security in mind.
Added 4 months ago
C
Apps Development Sr Manager - Vice President
Citi
Remote, Canada
- Full-time
- Remote
The Senior Technology Lead must be experienced hands-on engineer who is passionate about solving business, customer, and technology problems through innovation and perseverance. Responsible…
Added 3 months ago
AI Native Engineer
CookUnity
Toronto, Ontario
You'll embed directly with the cross functional AI team as a dedicated AI engineer. Your job isn't to write code faster with AI. It's to fundamentally redesign how work gets done. You'll…
Added 4 months ago
C
Applications Development Sr Programmer Analyst - Assistant Vice President
Citi
Remote, Canada
- Full-time
- Remote
We are seeking a highly motivated and experienced Principal Engineer to join our Retail and Wealth Risk Engineering team under the Enterprise Risk Technology platform. This is an…
Added 4 months ago
Network Engineer, Foundation and Support (Edge/Backbone Infrastructure Design)
Meta
Quinte West, Ontario
…this role, we are looking for a Network Infrastructure Design Engineer with demonstrated experience in developing and delivering network infrastructure solutions at scale in a data center…
Added 4 months ago
Network Engineer, Foundation and Support (Edge/Backbone Infrastructure Design)
Meta
Quinte West, Ontario
…this role, we are looking for a Network Infrastructure Design Engineer with demonstrated experience in developing and delivering network infrastructure solutions at scale in a data center…
Added 4 months ago
EI
Senior Integrations Developer / AI Data Integration Engineer
Engineered Intelligence Inc.
Mississauga, Ontario
- Full-time
We are looking for an experienced and hands-on Senior Integrations Developer / AI Data Integration Engineer to help lead the evolution of our modern data integration platform. This role…
Added 4 months ago
Network Engineer, Foundation & Support (DC Design)
Meta
Quinte West, Ontario
…this role, we are looking for a Network Infrastructure Design Engineer with demonstrated experience in developing and deploying network connectivity solutions at scale in a data center or…
Added 2 months ago
GM
Senior Software Developer - Test Automation
General Motors
Remote, Canada
- Full-time
- Remote
You will join our engineering organization as a Software Development Engineer in Test (SDET), responsible for building robust, scalable, and automated testing solutions that ensure the…
Added 4 months ago
BC
Senior Business Intelligence Engineer
BFL CANADA
Montreal, Quebec
- Full-time
We are looking for a Senior Business Intelligence Engineer to join our Business Intelligence team in our Montreal office!
Added 4 months ago
TC
Senior Software Engineer
Treewalk Consulting Inc.
Remote, Canada
- Full-time
- Remote
…AI in the accounting and finance space. The Senior Software Engineer will be the hands-on architect and builder of the new systems shaping our business - and the technical counterpart to…
Added 6 months ago
S
Senior/Lead Risk Analyst, Payment fraud
Snaplii
Toronto, Ontario
- Full-time
…who just read reports; we want strategists who can reverse-engineer fraud loops and command AI to automatically sever…
Added 2 months ago
EM
Senior Software Engineer - Backend
Evertz Microsystems Limited
Burlington, ON
- Full-time
We are seeking a highly motivated Senior Software Engineer to join our growing engineering team. This role offers an exciting opportunity to design and build scalable, production grade…
Added 5 months ago
T
Senior Software Engineer, Site Reliability Engineering
Thumbtack
Remote, Canada
- Full-time
- Remote
…work with engineering teams ranging from product development, developer experience, and backend infrastructure to collaboratively build Thumbtack’s ecosystem of platform services that have…
Added 5 months ago
MC
Senior Electrical Engineer
Mission Control Space Services
Ottawa, Ontario
- Full-time
Familiarity with embedded C/C++ or scripting (Python, MATLAB) for testing and automation
Added 5 months ago
MC
Senior GNC Robotics Engineer
Mission Control Space Services
Ottawa, Ontario
- Full-time
Proficiency in simulation and modeling tools (e.g., MATLAB/Simulink, Python-based frameworks).
Added 5 months ago
MC
Senior Mechanical Engineer
Mission Control Space Services
Ottawa, Ontario
- Full-time
Mission Control is seeking a Senior Mechanical Engineer to play a key technical leadership role in expanding our portfolio of autonomous and robotic space systems.
Added 5 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 5 months ago
H
AI Solutions Architect
HireHawk
Remote, Canada
- Full-time
- Remote
Added 2 months ago
Developer, Cloud Engineering
Scotiabank
Toronto, ON
We are looking for an energetic and results-driven Cloud Engineer who is passionate about technology and is excited to play a key role in advancing the bank on its cloud strategy by…
Added 5 months ago
GP
Staff Software Engineer
Generac Power Systems
Remote, Canada
- Full-time
- Remote
Proficiency in multiple programming languages and frameworks including Go, Java, TypeScript, C++, Python, etc.
Added 3 months ago
Senior Data Engineer, AI Systems
Movable Ink
Toronto, Ontario
…some of the world's largest consumer brands. As a Senior Data Engineer, you will own the Spark-based data pipelines and data infrastructure at the heart of this system - building, scaling,…
Added 5 months ago
S
Software Engineer III (FC Ops)
Spreetail
Winnipeg, Manitoba
- Full-time
Spreetail is looking for a Software Engineer III to join our team. Spreetail is a technology-driven e-commerce company that owns and operates the full retail supply chain (from manufacturer…

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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