Skip to content
CV Rocket
Get started
How it worksThe enginePricingBlogContactSign in

Open nowPosted 3 days agoWe saw it 101 min after it went up

Senior Technical Support Engineer

Sentry43 open roles

Pay
$125,000 – $150,000 a year
Where
Toronto, Ontario, Canada
Work mode
Hybrid
Get the CV for this job

From $25 per CV, paid once. No subscription.

Your applicationOpen nowSenior Technical Support EngineerSentry · Toronto, Ontario, Canada

  1. YouYes, apply to this one.

  2. CV RocketCV written for this posting.

  3. 25 readersRecruiter, hiring manager, skeptic. Round after round.

  4. CV RocketApplied on Sentry's own form.

The reply lands in your private mailbox

3×more interviews than doing it yourself with ChatGPT.

The clock on this job

Early applications get read.

7.9% of postings close within 7 days. Measured by our own scanner across the market. Sentry postings stay open a median of 41 days.

Share of postings closed within
  1. 1.6%1 day
  2. 3.6%3 days
  3. 7.9%7 days
  4. 14.9%14 days
  5. 34.0%30 days
This job: posted 3 days ago

Sentry median: 41 days open

The posting

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 https://sentry.io/careers/ 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 https://sentry.io/careers/applicantprivacy/.

From $25, paid onceGet the CV for this job

What happens when you press

One press. We do the rest.

  1. A CV for this posting

    Written against Sentry's own wording, from every piece of relevant proof in your profile.

  2. 25 readers review it

    Recruiter, hiring manager, skeptic and more read every draft, round after round. You get the best round.

    The review screen in CV Rocket: how each CV was read, round by round.

  3. We apply on Sentry's form

    Our application engine gets through the hardest forms there are. Where a question needs you, AI suggests the best answer. Don't want us applying from our IP addresses? Use our Chrome extension: we apply straight from your own browser.

    An application in CV Rocket: every answer filled in on the employer's form.

  4. Every reply, sorted

    Sentry's answer lands in your private mailbox, and we classify it on arrival: interview, question, rejection.

    The CV Rocket inbox: each employer reply classified as an interview, an action or a rejection.

  5. Reply with AI

    AI helps you write the email, checks it and sends it. We show you whether the recruiter read it.

  6. The interview in your calendar

    Full integration with your calendar. The invitation goes straight in.

    An interview invitation in the CV Rocket inbox, added to the candidate's calendar.
Get the CV for this job

From $25 per CV, paid once. No subscription.

Why it works

3×

more interviews than doing it yourself with ChatGPT.

ChatGPT writes a CV and never learns what happened to it. We see every reply. For each CV we know:

  • How it was written, and how the review scored it
  • When we applied, and how long after the posting went up
  • Which posting, which company, which city
  • Who got the interview, and who heard nothing

That is how we know which CVs get called.

Get the CV for this job

From $25 per CV, paid once. No subscription.

The numbers game

More applications. More interviews.

Every application goes out with its own CV, written for that posting and paid once. Send enough of them and the law of large numbers finds you the job.

Get the CV for this job
By hand5–10
With CV Rocket100
applications a day

Nearby

Live postings like this one

Same employer first, then the same role elsewhere.

Before you press

Straight answers

Get the CV for this job

From $25 per CV, paid once. No subscription.

What if my background isn't good enough?

We make the most of the background you have. The CV uses every piece of relevant proof your profile holds, and one of the 25 readers reads your whole profile and flags what the CV left out.

Do you really apply for me?

Yes, on the employer's own form, the hardest ones included. Where a question needs you, you answer it right there and AI suggests the best answer. Don't want us applying from our IP addresses? Use our Chrome extension: we apply straight from your own browser.

Is it a subscription?

No. You pay once per CV, from $25. Every application goes out with its own CV, written for that posting.

One job. One CV.
Paid once.

Pick the posting you want. We write for it, apply for you and catch the reply.

Get the CV for this job

From $25 per CV, paid once. No subscription.