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Staff Software Engineer, Issues

Sentry sentry.io Open · verified Oct 24, 2026
Hybrid Toronto San Francisco Full-time Senior Engineering Leadership

At a glance

Senior Engineering Leadership role at Sentry. Toronto · full-time · CA$253,000–CA$316,000 base.

SalaryStated by Sentry
CA$253,000 – CA$316,000
Base salary for this role, in CAD per year, as published in the posting.
This role, from SentryOur estimate for the market: CA$136,650–CA$217,100Median CA$177,500
Above the market median of CA$177,500 for senior engineering leadership roles in Toronto.
Worked out from 55 postings that stated pay, median CA$177,500. Last updated Oct 21, 2026.
RoleEngineering Leadership
SenioritySenior
LocationToronto
WorkplaceHybrid
EmploymentFull-time
Base payCA$253,000–CA$316,000
PostedMar 31, 2026 · 6mo ago
Also hiring inSan Francisco
Role brief

techroles summary, based on the employer's posting.

What you'll do

  • Set technical direction for Issue Workflow and plan its multi-quarter roadmap with engineering, product and design partners
  • Choose architectural approaches and technologies, address technical debt, and build a foundation that can scale
  • Improve performance and scalability across issue grouping, search, data pipelines and analysis systems
  • Shape interfaces, error messages and loading behavior, then instrument features to track product quality
  • Coach engineers in systems design, coding practices and product thinking

What you bring

  • At least ten years of full-stack software engineering experience, ideally using Python and TypeScript
  • Strong knowledge of domain modeling, distributed systems, data stores and message queues
  • Clear written and spoken communication skills

Who this fits

This senior technical leadership role suits a product-minded engineer with deep distributed-systems experience and full-stack perspective. You’ll work hybrid in Toronto and mentor other engineers.

From the employer

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

Issue Workflow is Sentry's primary product surface. Our issue platform processes billions events daily and turns them into actionable insights that help millions of developers fix bugs faster.

As a Staff Software Engineer on the Issues team, you'll architect the systems that power this experience. You'll work at the intersection of high-scale distributed systems and product engineering, building real-time data pipelines, search backends, and analysis systems that surface signal from noise. This is product engineering at massive scale—where every architectural decision impacts millions of debugging sessions.

You'll be the technical leader who shapes how Sentry groups issues, how we make search lightning-fast, how we enable sophisticated agentic workflows, and how we ensure that the product is performant even at billions-of-events scale. Your work will define what's possible for the most trafficked part of Sentry's platform.

In this role you will

  • Drive technical strategy and roadmap. Partner with engineering leadership, product, and design to shape the multi-quarter technical vision for Issue Workflow platform. Make strategic calls about architectural direction, technology choices, and technical debt. Ensure the team is building a strong foundation to scale with Sentry's growth.

  • Solve complex performance and scalability challenges.

  • Champion product quality and user experience. Build features that don't just work—they delight. You understand that milliseconds matter in the developer experience. You sweat the details of interfaces, error messages, loading states, and edge cases. You instrument everything so the team can measure and improve.

  • Mentor and elevate others. You've helped engineers grow their skills. You celebrate wins and learn from failures alongside your teammates.

You’ll love this job if you

  • Are a distributed systems engineer who understands the realities of high-scale architectures. You know about eventual consistency, partitioning strategies, caching layers, and query optimization. You've debugged enough systems at scale that you now know to design for failure and build systems that degrade gracefully.

  • Are product-minded and understand that great engineering serves users. You collaborate effectively with Product and Design, offering technical perspectives that shape better products. You can explain technical constraints in user-centric terms. You get excited about making developers' lives better, not just solving technical puzzles.

  • Have strong full-stack instincts. While this role is backend-heavy, you understand the entire system from data ingestion to what renders in the browser. You know enough about frontend performance, API design, and user experience to make good architectural decisions that consider the whole picture.

  • Include and uplift others. You've helped engineers grow their skills in systems design, coding practices, and product thinking. You're generous with knowledge and patient in explaining complex concepts. You celebrate wins and learn from failures alongside your teammates.

Qualifications

  • 10+ years in full-stack software engineering, ideally Python and Typescript

  • Expertise in domain modeling, distributed systems, data stores, message queues

  • Excellent written and verbal communication skills

  • Experience with PostgreSQL, ClickHouse, and Kafka is preferred

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.

Opportunity

Engineering Leadership work from LinkedIn, X, Reddit and Upwork, in one list.

Each morning you get everything that fits, strongest first.

Engineering Leadership

Find me work

By the team behind techroles.

Find me work
Opportunity

Engineering Leadership work from LinkedIn, X, Reddit and Upwork, in one list.

Each morning you get everything that fits, strongest first.

Find me work

By the team behind techroles.