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Added 3 months ago
Senior Transmission Line Engineer - Grid
Sargent & Lundy
Toronto, ON · North York, ON
Full-time
Work with vendors and clients to specify transmission line components.
Added 2 months ago
Senior Back End Engineer (Data Platform)
Forma.ai
Toronto, Ontario
As a Senior Engineer, Data Platform, you are expected to operate with strong ownership and sound technical judgment. This includes identifying risks in the work you own, surfacing edge…
Added 2 months ago
Senior Software Engineer (Applications)
Forma.ai
Toronto, Ontario
As a Senior Backend Engineer, you are expected to operate with strong ownership and sound technical judgment. This includes identifying risks in the work you own, surfacing edge cases,…
Added 3 months ago
Senior Product Engineer
Docebo
Remote, Canada
$102,800 to $137,000 CAD / year
Full-time · Remote
As a Senior Product Engineer at Docebo, you operate at the intersection of customer needs and product delivery. You'll own the full lifecycle of the features you build - from identifying…
Added 5 days ago
Senior Forward Deployed Engineer (Hybrid, Canada)
Unit8 SA
Remote, Canada
Full-time · Remote
…Unit8 is expanding into the Canadian market. We are seeking a Senior Forward Deployed Engineer who will work directly with customers, owning delivery strategy and…
Added 3 months ago
Senior DevOps Engineer
Huzzle
Remote, Canada
Full-time · Remote
We are hiring an experienced Senior DevOps Engineer to support fast-growing international companies building scalable cloud-native platforms and enterprise infrastructure.
Added 3 months ago
Future Opportunities: Sr Software Developer - Platform Engineering
Wealthsimple Technologies
Remote, Canada
$151,200 to $189,000 CAD / year
Full-time · Remote
…measured by the leverage we give them. Our work shapes how every engineer at Wealthsimple writes, ships, and runs code. When we do it well, the whole company moves faster and ships with…
Added 3 months ago
Senior Data Developer
Vancouver Coastal Health
Vancouver, British Columbia
$46.39 to $66.68 CAD / hour
Full-time
Come work as a Senior Data Developer with Vancouver Coastal Health (VCH)!
Added 21 days ago
Staff Software Engineer - Capital One Travel Tech - Full-stack
Capital One
Toronto, ON
Full-time
…in-house and building the next generation of our travel ecosystem. With Capital One Business Travel (COBT) scaling rapidly, our integration with Brex is the catalyst propelling us from…
Added 3 months ago
Cloud Networking Senior Engineer
Aptiv
Kanata, Ontario
Full-time
Strong proficiency in Python, C/C++, and/or Go, with experience building backend or infrastructure components
Added 3 months ago
Cloud Platform - Senior Engineer Storage
Aptiv
Kanata, Ontario
Full-time
…milestones including the world’s first successful 5G data session with Verizon and building one of the largest Open RAN networks in the world with…
Added 3 months ago
Senior Software Engineer, Integrations
d1g1t
Toronto, Ontario
Full-time
As a Senior Engineer, you won't just be writing code - you will be a vital technical voice and project leader. You will bridge the gap between business needs and complex data systems,…
Added 1 month ago
AI Prompt Engineer
MCI Careers
Canada
Full-time
The successful candidate will work closely with AI Engineers, Product Teams, Data Scientists, and Senior Prompt Engineers to improve AI interactions and support the development of…
Added 1 month ago
Senior Generative AI Engineer
MCI Careers
Canada
Other
We are seeking a Senior Generative AI Engineer to lead the development of advanced AI-powered products and enterprise solutions. This role requires deep expertise in Large Language Models,…
Added 1 month ago
Senior RAG Engineer
MCI Careers
Canada
Other
We are seeking a Senior RAG Engineer to lead the design and optimization of Retrieval-Augmented Generation platforms that power enterprise AI solutions. This role requires expertise in…
Added 1 month ago
Senior AI / ML Engineer
MCI Careers
Canada
Other
We are seeking a highly experienced Senior AI / Machine Learning Engineer to lead the design, development, and deployment of advanced AI and machine learning solutions that drive innovation…
Added 15 days ago
Senior Data Software Engineer
Scotiabank
Toronto, ON
As a Senior Software Engineer on Scotiabank’s Data & AI Technology team, you will lead the design, development and scaling of our enterprise data catalog and data management solutions…
Added 3 months ago
Principal Software Engineer - Distributed Systems
Microsoft
Vancouver, British Columbia
Full-time
The Fabric Mirroring team is currently seeking a Senior Software Engineer to join their team. This team oversees designing, building, and operating a next generation service that transfers…
Added 3 months ago
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 3 months ago
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 1 month ago
Senior Machine Learning Research Engineer
Royal Bank of Canada
Toronto, ON
Full-time
We’re looking for an enthusiastic Senior Machine Learning Research Engineer who’s excited by the opportunity of being at the forefront of applying machine learning technology to challenging…
Added 3 months ago
Apps Development Sr Manager - Vice President
Citi
Mississauga, Ontario
Full-time
A senior-level position responsible for accomplishing results by designing, implementing, and managing the firm's engineering platforms, with a focus on CI/CD, container orchestration, and…
Added 3 months ago
Apps Development Sr Manager - Vice President
Citi
Remote, Canada
Full-time · Remote
The Applications Development Senior Manager is responsible for accomplishing results through the management of a team or department in an effort to establish and implement new or revised…
Added 24 days ago
Senior Staff Machine Learning Engineer, Menu Personalisation
HelloFresh
Toronto, ON
Fluency across our data and ML stack (Python, Spark) and our backend and platform stack (Go, Kafka, Kubernetes), with hands-on experience across pipelines, model serving, and observability…
Added 3 months ago
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…

Sentry

Technical Support Engineer

Remote, Canada

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

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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 [email protected].

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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