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Added 1 month ago
Staff FullStack Engineer, Okta Secures AI
Okta
Toronto, ON
$160,000 to $220,000 CAD / year
Full-time
You will lead the technical implementation of our four-pillar maturity model - Discover, Onboard, Protect, and Govern - to provide enterprise-grade visibility and governance for both human…
Added 1 month ago
Head of Toronto AI Center
Samsung Research America
Toronto, ON
…translate research and innovation into tangible outcomes. We lead in machine intelligence by building AI that is user-centric and physically grounded - AI that understands not just what…
Added 1 month ago
Java Developer, TD Securities
TD
Toronto, ON
Full-time
Lead technical discussions and high-performance professionals at various capacity (junior to senior developer)
Added 1 month ago
Director - Solution Delivery, Wealth Management
Scotiabank
Toronto, ON
Lead the design, architecture, and delivery of high-quality, enterprise-scale solutions that address complex business challenges.
Added 1 month ago
Software Engineer, Full-Stack Applications, Associate Director
Fitch Group
Toronto, ON
…highly experienced software engineer with deep expertise in Java and React, strong software engineering fundamentals, and a passion for building scalable, reliable, and user-focused…
Added 1 month ago
Staff FullStack Engineer, Okta Secures AI
Okta
Waterloo, ON
$160,000 to $220,000 CAD / year
Full-time
You will lead the technical implementation of our four-pillar maturity model - Discover, Onboard, Protect, and Govern - to provide enterprise-grade visibility and governance for both human…
Added 1 month ago
Lead Software Engineer, Full-Stack Applications - Innovation Teams
Fitch Group
Toronto, ON
Lead Software Engineer, Full-Stack Applications – Innovation Teams
Added 1 month ago
Lead Data and AI Engineer
Sanofi
Toronto, ON
Full-time
Lead, mentor, and develop a team of data engineers while fostering strong engineering practices, accountability, collaboration, and continuous improvement
Added 1 month ago
Senior Data Engineer
Kainos
Halifax, NS
Full-time
…code, test and defect resolution. Working with Architects and Lead Engineers to ensure the software supports non-functional needs. Collaborating with colleagues to resolve implementation…
Added 4 months ago
Project Manager | HRBrain
HRbrain Inc.
Mississauga, ON
Contract
…frameworks, and systems structure. The successful candidate will lead technical deliveries for large-scale Telecom projects, utilizing both traditional Waterfall and modern Agile…
Added 1 month ago
Lead Software Engineer (SDET)
Mastercard
Toronto, ON
Full-time
Lead Software Engineer (SDET)Who is Mastercard?
Added 28 days ago
SR&ED Technical Advisor, Director
Pwc Canada
Toronto, ON
Full-time
Lead the completion of SR&ED claims (Canada) and R&D tax credit claims (US).
Added 1 month ago
Dev Lead
J&M Group
Toronto, ON
Contract
We are hiring a Dev Lead with strong expertise in application development and maintenance, with hands-on experience in Java/J2EE, Spring Boot, REST APIs, Microservices, AWS, and NodeJS. The…
Added 1 month ago
Full Stack Developer Lead (Java, Python, AWS, NodeJS)
Pacer Group
Toronto, ON
$45 to $50 CAD / hour
Contract
Job Title: Full Stack Developer Lead (Java, Python, AWS, NodeJS)
Added 2 months ago
Software Engineer I
Beanfield
Toronto, ON
$90,000 to $110,000 CAD / year
Full-time
Java Programmer or Developer certifications from Oracle
Added 2 months ago
AI Architect
Synopsys Inc
Mississauga, ON
Full-time
…Intelligence, from self-driving cars to learning machines. We lead in chip design, verification, and IP integration, empowering the creation of high-performance silicon chips and…
Added 1 month ago
Lead Core Backend Developer
Citi
Mississauga, ON
Full-time
We are looking for a talented and passionate individual to join our Java Server development team and continue to evolve our next-generation rates reference data application.
Added 1 month ago
Senior Java Developer
Citi
Mississauga, ON
Full-time
We are seeking a highly experienced and motivated Lead Java Developer with 6+ years of industry experience to spearhead the development of robust, scalable, and innovative enterprise…
Added 1 month ago
Senior Lead Java Fullstack Software Engineer
Citi
Mississauga, ON
Full-time
The Applications Development Technology Senior Lead Analyst is a senior level position responsible for establishing and implementing new or revised application systems and programs in…
Added 19 days ago
Data Solutions Architect
Spaulding Ridge
Toronto, ON
Ability to lead end-to-end solution architecture across source systems, integration layers, Snowflake, transformation logic, semantic/reporting layers, APIs, and user-facing applications.
Added 1 month ago
SR&ED Technical Advisor, Director
PwC
Toronto, ON
Full-time
Lead the completion of SR&ED claims (Canada) and R&D tax credit claims (US).
Added 1 month ago
Utility Application Technical Architect
Capgemini
Vancouver, BC
Lead root cause analysis activities and implement sustainable solutions to improve application stability and reliability.
Added 1 month ago
Java Technical Lead
J&M Group
Toronto, ON
Full-time
We are seeking a highly experienced Java Technical Lead with 12+ years of hands-on experience in enterprise application development and production support. The ideal candidate will possess…
Added 1 month ago
Cybersecurity Lead
e-STORAGE
Kitchener, ON
Full-time
We are seeking a highly skilled and motivated Cyber Security Lead to join our team and contribute to the development of on-premises Energy Management System (EMS) for utility grade systems.…
Added 2 months ago
Senior Data Engineer
Kainos
Halifax, NS
Full-time
…code, test and defect resolution. Working with Architects and Lead Engineers to ensure the software supports non-functional needs. Collaborating with colleagues to resolve implementation…

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 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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