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Added 29 mins ago
Android Infrastructure Software Developer
Google
Waterloo, ON
Development experience working with Kotlin or Java.
Added 29 mins ago
Technical Solutions Development Manager, Compute, Google Cloud
Google
Waterloo, ON
…we have the expertise, tools, and processes to resolve deep technical issues customers encounter. You will handle customer escalations by combining business acumen with technical skills,…
Added 3 hours ago
Industrial Software Validation|
Husky Technologies
Bolton, ON
Full-time
…passion of our people around the world and their desire to lead change. At the same time, we are not afraid to expect a lot and strive for leadership in all of our key markets. We are a…
Added 4 hours ago
Senior Fullstack (Node/Typescript/Angular)
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Lead application and framework upgrades, including dependency analysis, compatibility assessments, remediation, and identification of potential breaking changes.
Added 5 hours ago
Lead Developer – Innovateur AI & GitHub Copilot
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Full-time
Drive the future of software development using GitHub Copilot, ChatGPT and AI-powered tools. As Lead Developer, you will boost productivity, mentor technical teams, and shape…
Added 5 hours ago
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Added 6 hours ago
Java Fullstack Architect
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Mississauga, ON
Full-time
We are seeking a highly skilled Java Architect with 15+ years of experience designing and delivering enterprise-scale applications. The ideal candidate will possess strong expertise in Java…
Added 7 hours ago
SOC Development Engineer
Solidigm
Vancouver, BC
Full-time
…in Asia, Europe, and the Americas. Solidigm will continue to lead the world in innovating new Memory technologies with aspirations to be the #1 NAND memory company in the world. At…
Added 7 hours ago
Senior Technical Support Engineer
Sentry
Remote, Canada
$125,000 to $150,000 USD / year
Full-time · Remote
…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…
Added 8 hours ago
SOC Development Engineer
Solidigm
Vancouver, BC
$134,000 to $201,000 CAD / year
Full-time
…in Asia, Europe, and the Americas. Solidigm will continue to lead the world in innovating new Memory technologies with aspirations to be the #1 NAND memory company in the world. At…
Added 8 hours ago
Applications Development Technology Senior Lead
Citi
Mississauga, ON
Full-time
The Applications Development Technology Senior Lead is a senior level position responsible for establishing and implementing new or revised application systems and programs in coordination…
Added 9 hours ago
Industrial Software Validation|
Husky Technologies
Bolton, ON
Full-time
…passion of our people around the world and their desire to lead change. At the same time, we are not afraid to expect a lot and strive for leadership in all of our key markets. We are a…
Added 9 hours ago
Full Stack Developer Lead (AWS Lambda)
Dawn InfoTek
Toronto, ON
Full-time
Strong technical leadership experience as a Technical Lead, including:
Added 9 hours ago
Sr. Data Analyst -1806 (Asset Management)
Amyantek
Toronto, ON
Contract
4. Strong programming skills in Python, Java, Scala, and SQL.
Added 9 hours ago
Senior SailPoint IIQ Engineer
Cognizant
Brampton, ON
Full-time
We are seeking a Lead SailPoint IdentityIQ Engineer with strong expertise in Identity Governance and Administration (IGA), SailPoint IdentityIQ implementation, and IAM operations. This role…
Added 9 hours ago
Senior Java Microservices Engineer
Publicis Sapient
Calgary, AB
Full-time
We are looking for highly skilled Senior Java Microservices Engineer to join a strategic client engagement in Calgary. We are looking for a hands-on senior engineer who combines strong…
Added 10 hours ago
Senior Data Engineer (Snowflake & Asset Management)
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Toronto, ON
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…data, cloud, and software engineering needs. Collaborate with technical leads to align engineering decisions with the organization's strategic vision. Build scalable data pipelines, data…
Added 10 hours ago
Senior QA Engineer III – Automation | Banking | API | Kafka | ETL (35729)
Myticas Consulting
Ottawa, ON
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…issues, contributing to overall QA strategy, and providing technical guidance to other QA…
Added 11 hours ago
Senior Software Developer, BE
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As a Staff Software Developer on the Monetization team, you'll lead technical initiatives and take significant ownership over service architecture, product API development, and data…
Added 11 hours ago
Senior Software Engineer
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Toronto, ON
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As a Senior Software Engineer, you will play a critical role in defining the architecture and technical vision for Supernova’s cloud-based Security-Based Lending (SBL) SaaS platform. You…
Added 11 hours ago
Senior Backend Principal Developer - Vice President
Citi
Mississauga, ON
Full-time
Demonstrated experience in a Principal or Lead Developer role, with a strong track record of technical leadership and hands-on contribution.
Added 11 hours ago
Java Developer
LTM
ON · Ontario, Canada
$85,000 to $120,000 USD / year
Full-time
Lead the development lifecycle of Javabased applications within the Java Frameworks domain Mentor junior developers and provide technical guidance on Java best practices and framework usage…
Added 11 hours ago
Staff Software Engineer, OIN
Okta
Toronto, ON
$160,000 to $220,000 CAD / year
Full-time
Lead discovery and technical scoping for new requirements, turning ambiguous product asks into a concrete architecture, phased delivery plans, and credible estimates, in close partnership…
Added 11 hours ago
Java Architect
Futran Solutions
Mississauga, ON
Full-time
We are seeking a highly skilled Java Architect with 15+ years of experience designing and delivering enterprise-scale applications. The ideal candidate will possess strong expertise in Java…
Added 12 hours ago
Staff Software Engineer, OIN
Okta
Toronto, ON
Lead discovery and technical scoping for new requirements, turning ambiguous product asks into a concrete architecture, phased delivery plans, and credible estimates, in close partnership…

Sentry

Senior Technical Support Engineer

Remote, Canada

Pay: $125,000 to $150,000 USD / year
Job type: Full-time
Workplace: Remote
Experience: 5–8+ 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: Sep 30, 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

5–8+ 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 $125,000 to $150,000. 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

You will act as a technical lead for agentic operations, performing deep-dive debugging and root-cause analysis on complex issues. Additionally, you will engineer autonomous support paths and build context into systems to resolve high-impact architectural puzzles.

Requirements

Candidates must have 5-8+ years of experience in technical support, systems engineering, or software development with mastery of Python, JavaScript, Java, or Ruby. Strong knowledge of distributed systems, APIs, and AI/LLM orchestration is required to succeed in this role.

Skills

Technical support engineering
Systems engineering
Software development
Python
JavaScript
Java
Ruby
Distributed systems
Microservices
APIs
LLM orchestration
RAG
Debugging
Root-cause analysis
Distributed tracing
Agentic operations

Benefits

Incentive compensation
Equity grants
Paid time off
Group health insurance coverage

Visa sponsorship

Not detected in the job text

Keywords

Technical Support
Systems Engineering
Software Development
SaaS
Python
JavaScript
Java
Ruby
Distributed Systems
Microservices
APIs
LLM
RAG
Debugging
Observability
SDK
Agentic Ops
MCP
GitHub
Discord
CI/CD
Automation
Architecture
Root-cause analysis
Developer Advocate

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