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Added 2 months ago
Senior Backend Engineer - Lodging and Cars
Hopper
Remote, Canada
$220,000 to $300,000 CAD / year
Full-time · Remote
As a senior-level individual contributor, you will navigate a complex microservices environment to deliver reliable booking fulfillment, integrate new lodging and cars partners into our…
Added 2 months ago
Développeur(-euse) principal d’application mobile − Android / Senior Mobile Developer – Android
Expedia
Montreal, Quebec · Canada - Quebec - Montreal
Full-time
Maîtrise approfondie du développement Android (Kotlin/Java, Android SDK, frameworks UI), y compris la conception d’API, la modélisation de données et la conception de systèmes pour les…
Added 2 months ago
Développeur(-euse) de logiciels sénior(e) (contenu) / Senior Software Development Engineer
Expedia
Montreal, Quebec · Canada - Quebec - Montreal
Full-time
Développeur(-euse) de logiciels sénior(e) (contenu)
Added 25 days ago
Senior Software Enginner- Global Payments Engineering
Scotiabank
Toronto, ON · Scarborough, ON
Technical understanding – as a standard Software Engineer there will be expectations that you are able to lead technical discussions, challenge design and strategy
Added 20 days ago
VP Java Low Latency Senior Developer
Citi
Remote, Canada
Full-time · Remote
Citi Equities Technology organization is looking for an experienced and senior Java Low Latency Senior Developer to join the NAM Equities Electronic Trading team to help take our platforms…
Added 17 days ago
Software Engineer - Retailer Experience & Growth - Fullstack, Backend or Frontend
Faire
Toronto, ON · Kitchener, ON
As a Senior Engineer on our Growth team, you'll build products and experiments that directly influence how retailers discover, adopt, and engage with Faire. Your work will sit at the…
Added 13 days ago
Staff Software Engineer - UI Platform
Okta
Toronto, ON
…We are looking for an experienced full stack Staff Software Engineer (with a focus on UI) who is passionate about building large-scale, mission-critical infrastructure in a fast-paced agile…
Added 3 months ago
Tech Lead, Software Development
Univeris
Toronto, Ontario
Full-time
At Univeris, a Software Development Technical Team Lead is a hands-on senior software engineer and people manager, accountable for the technical design, development, quality of…
Added 3 months ago
Senior Platform Engineer
Scalar
Remote, Canada
$150,000 to $250,000 CAD / year
Full-time · Remote
SDK generation - turning a customer's OpenAPI document into type-safe client libraries across TypeScript, Python, Go, PHP, Java, and Ruby, with code samples and automated GitHub sync
Added 1 month ago
Senior Staff Software Engineer - Mobile(Android)
Capital One
Toronto, Ontario
Full-time
161 Bay Street (93021), Canada, Toronto,Toronto, Ontario,Senior Staff Software Engineer - Mobile(Android)
Added 9 days ago
Senior Automation Engineer
Tubi - Canada
Toronto, ON
We are looking for a talented Automation Engineer to join our Automation Engineering team in Toronto. In this role, you will be responsible for designing and implementing automated tests…
Added 2 months ago
Senior Technical Support Analyst
Verily
Remote, Canada
Full-time · Remote
…across a number of program offerings. As a Sr Software Support Engineer, you will work closely with internal stakeholders to identify, reproduce, troubleshoot and resolve deep technical…
Added 3 months ago
Senior Product Engineer I - PHP
Docebo
Remote, Canada
$102,800 to $137,000 CAD / year
Full-time · Remote
As a Senior Product Engineer I at Docebo, you aren't just writing code; you are the architect of a world-class SaaS platform that empowers millions to learn and grow. You’ll join a…
Added 1 month ago
Senior Software Developer
Autodesk
Toronto, ON · AMER - Canada - Ontario - Toronto - University Ave
Full-time
Excellent programing skills with Java, React Typescript.
Added 3 months ago
Senior Software Engineer - Professional Services
Trackunit
London, Ontario
Full-time
As a Software Engineer in Trackunit’s Professional Services team, you’ll join a growing group of engineers building tailored solutions on top of IrisX – our operating data platform -…
Added 3 months ago
Lead Full Stack Developer
Publicis Groupe Holdings B.V
Toronto, Ontario
Full-time
…database migration, debugging a prod incident, mentoring a senior engineer, or sitting in a client architecture conversation. You thrive at the intersection of architecture, engineering,…
Added 3 months ago
Senior Consultant IIQ
Cyderes
Canada
Full-time
We are seeking an experienced Senior SailPoint IdentityIQ (IIQ) Engineer to join our Identity and Access Management (IAM) team. This individual will be responsible for designing,…
Added 1 month ago
Staff Software Engineer - Capital One Travel Tech - Full-stack
Capital One
Toronto, Ontario
Full-time
…serving small businesses to powering enterprise giants. As a Senior Engineer, you will be at the epicenter of this game-changing integration, architecting seamless connections across Brex,…
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 21 days ago
Staff Software Engineer - Capital One Travel Tech - Full-stack
Capital One
Toronto, ON
Full-time
…serving small businesses to powering enterprise giants. As a Senior Engineer, you will be at the epicenter of this game-changing integration, architecting seamless connections across Brex,…
Added 25 days ago
Software Engineer
Kaseya Careers
Toronto, ON
We’re hiring a Senior Software Engineer to provide technical leadership across enterprise SaaS platforms and strategic engineering initiatives. This role focuses on Java-based platform…
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…

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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