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Added 26 mins ago
Cemetery and Funeral Planning Partner
THE BEECHWOOD CEMETERY
Ottawa, ON
$100,000 to $150,000 CAD / year
Full-time
As the National Cemetery of Canada, our every-day is dedicated to delivering high-quality service to honor our ancestors and set a precedent for future generations; we are Beechwood…
Added 26 mins ago
Incident Manager
Bell
Mississauga, ON
…Problems ‘related to customers’. Our business model is highly customer-centric, with shared accountability between Service teams for managing customer issues. This seamless approach to…
Added 26 mins ago
Senior Technical Support & Success Manager
Trolley
Toronto, ON · Montreal, QC · Halifax, NS
Working closely with Product, Engineering, Sales, and Customer Success teams, you'll resolve complex technical issues, identify opportunities to improve customer outcomes, and advocate for…
Added 41 mins ago
Studio Coach - Smiths Falls, ON
Weight Watchers
Burnaby, BC
Added 41 mins ago
Studio Coach - Carleton Place, ON
Weight Watchers
Burnaby, BC
Added 55 mins ago
Sales Representative - Calgary, AB
Kognitive Sales Solutions
Calgary, AB
Full-time
Provide expectational customer service ensuring customers have a great experience
Added 1 hour ago
Commercial Placement and Marketing Coordinator
Sauce Recruitment Corp.
Winnipeg, MB
Full-time
We respect discretion and advocate for smart career choices.
Added 1 hour ago
Community General Manager II
CIBC
Richmond Hill, ON
Full-time
…people at all levels to re-think the way they do business. Advocate for CIBC within the community to recruit employees who share and demonstrate our…
Added 1 hour ago
Community General Manager, Personal & Business Banking - Charlottetown, PEI
CIBC
Charlottetown, PE
Full-time
…people at all levels to re-think the way they do business. Advocate for CIBC within the community to recruit employees who share and demonstrate our…
Added 1 hour ago
Community General Manager, Imperial Service
CIBC
Brampton, ON
Full-time
As a member of the Imperial Service Team, you’ll lead a team of client facing employees within the banking centre, as well as other banking centres within your community to deliver on…
Added 1 hour ago
Banking Centre Leader II
CIBC
Cambridge, ON
Full-time
…meet client financial needs while providing a high standard of service. Go above and beyond to advocate CIBC within the community to develop new and existing client relationships. Encourage…
Added 1 hour ago
Banking Centre Leader II
CIBC
Peterborough, ON · Toronto, ON
Full-time
…meet client financial needs while providing a high standard of service. Go above and beyond to advocate CIBC within the community to develop new and existing client relationships. Encourage…
Added 1 hour ago
Banking Centre Leader II
CIBC
Caledon East, ON
Full-time
…meet client financial needs while providing a high standard of service. Go above and beyond to advocate CIBC within the community to develop new and existing client relationships. Encourage…
Added 1 hour ago
Banking Centre Leader III
CIBC
Toronto, ON
Full-time
…meet client financial needs while providing a high standard of service. Go above and beyond to advocate CIBC within the community to develop new and existing client relationships. Encourage…
Added 1 hour ago
Community General Manager II
CIBC
Bolton, ON
Full-time
Banking Operations, Business Development, Client Service, Community Connections, Customer Experi
Added 1 hour ago
Banking Centre Leader - Dartmouth, NS
CIBC
Dartmouth, NS · PORTLAND & EISENER BANKING
Full-time
…meet client financial needs while providing a high standard of service. Go above and beyond to advocate CIBC within the community to develop new and existing client relationships. Encourage…
Added 1 hour ago
Banking Centre Leader III
CIBC
Toronto, ON
Full-time
…meet client financial needs while providing a high standard of service. Go above and beyond to advocate CIBC within the community to develop new and existing client relationships. Encourage…
Added 1 hour ago
Community General Manager I
CIBC
Burlington, ON
Full-time
…people at all levels to re-think the way they do business. Advocate for CIBC within the community to recruit employees who share and demonstrate our…
Added 1 hour ago
Financial Planner II (CIRO-ID)
CIBC
Brampton, ON
Full-time
As a member of the Imperial Service Team, you’ll manage and grow a dedicated client portfolio through key relationship management, creating comprehensive financial plans and providing…
Added 1 hour ago
Banking Centre Leader I
CIBC
ON · Haliburton
Full-time
…meet client financial needs while providing a high standard of service. Go above and beyond to advocate CIBC within the community to develop new and existing client relationships. Encourage…
Added 1 hour ago
Banking Centre Leader II
CIBC
Thunder Bay, ON
Full-time
…meet client financial needs while providing a high standard of service. Go above and beyond to advocate CIBC within the community to develop new and existing client relationships. Encourage…
Added 1 hour ago
Banking Centre Leader I
CIBC
Leamington, ON
Full-time
…meet client financial needs while providing a high standard of service. Go above and beyond to advocate CIBC within the community to develop new and existing client relationships. Encourage…
Added 1 hour ago
Banking Centre Leader III
CIBC
Toronto, ON
Full-time
…meet client financial needs while providing a high standard of service. Go above and beyond to advocate CIBC within the community to develop new and existing client relationships. Encourage…
Added 1 hour ago
Community General Manager, Imperial Service
CIBC
Maple, ON
Full-time
As a member of the Imperial Service Team, you’ll lead a team of client facing employees within the banking centre, as well as other banking centres within your community to deliver on…
Added 1 hour ago
Banking Centre Leader III
CIBC
Hamilton, ON
Full-time
…meet client financial needs while providing a high standard of service. Go above and beyond to advocate CIBC within the community to develop new and existing client relationships. Encourage…

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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