Staff Software Engineer (Issue Workflow)

Sentry; Toronto; On-site; CAD 120,000 - 150,000; Full time

Job summary

A leading software monitoring company in Toronto is seeking a Staff Software Engineer for their Issue Workflow team. The ideal candidate has over 10 years of full-stack software engineering experience, primarily in Python and Typescript. You will drive the technical strategy while mentoring other engineers, championing product quality, and solving complex scalability challenges. This role requires expertise in distributed systems and excellent communication skills, within a hybrid work model.

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.

Responsibilities

• Drive technical strategy and roadmap.
• Solve complex performance and scalability challenges.
• Champion product quality and user experience.
• Mentor and elevate other engineers.

Skills

Full-stack software engineering

Distributed systems

Product-minded engineering

Excellent communication skills

Python

Typescript

Tools

PostgreSQL

ClickHouse

Kafka

Job description

About Sentry

Bad software is everywhere, and we’re tired of it. Sentry is on a mission to help developers write better software faster so we can get back to enjoying technology.

With more than $217 million in funding and 100,000+ organizations that believe we’re on to something, we're building performance and error monitoring tools that help companies like Disney, Microsoft, and Atlassian spend less time fixing bugs and more time building products.

Sentry embraces a hybrid work model across our global hubs, with Mondays, Tuesdays, and Thursdays set as in-office anchor days to encourage meaningful collaboration. If you like to selfishly build things that make your digital life better, come help us build the next generation of software monitoring tools.

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 Issue Workflow 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 vision. 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 [e-mail].

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