Staff Software Engineer, Issue Workflow

Staff Software Engineer · Staff · Full Time

Toronto, Ontario, CanadaUSD 253k – 316k5mo ago
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Role

What you'll do.

Sentry is seeking a Staff Software Engineer for their Issue Workflow team, focusing on building high-scale distributed systems that process billions of events daily. The ideal candidate will be a technical leader who can architect sophisticated data pipelines, search backends, and analysis systems that transform complex software monitoring challenges into actionable developer insights.

Responsibilities

  • Technical Strategy: Partner with engineering leadership, product, and design to shape the multi-quarter technical vision for Issue Workflow platform. Make strategic architectural decisions and manage technical debt.
  • Performance Optimization: Solve complex performance and scalability challenges in high-scale distributed systems, ensuring the platform can handle billions of events daily.
  • Product Quality: Champion product quality by building features that not only function effectively but also provide an exceptional user experience, focusing on details like interfaces, error messages, and loading states.
  • Team Development: Mentor and elevate team members by sharing knowledge, helping engineers grow their skills in systems design, coding practices, and product thinking.

Qualifications

What we look for.

Technical

  • Programming Languages

    Proficiency in Python and TypeScript with 10+ years of full-stack software engineering experience

  • Distributed Systems

    Expert understanding of distributed system architectures, including eventual consistency, partitioning strategies, caching layers, and query optimization

  • Database Technologies

    Experience with PostgreSQL, ClickHouse, and Kafka for building high-performance data solutions

Education

  • Computer Science

    Bachelor's or Master's degree in Computer Science, Software Engineering, or related technical field preferred

Experience

  • Systems Architecture

    Proven track record of designing and implementing scalable, high-performance distributed systems

  • Technical Leadership

    Demonstrated experience in technical leadership, guiding architectural decisions and mentoring engineering teams

Skills

Required

  • Distributed Systems

    Deep understanding of high-scale system architectures and performance optimization

  • Full-Stack Engineering

    Comprehensive knowledge of backend and frontend technologies with a holistic system design approach

Preferred

  • Open Source Contribution

    Nice to have

    Experience contributing to or maintaining open-source projects

  • Performance Monitoring

    Nice to have

    Familiarity with application performance monitoring and error tracking tools

Tech stack

Languages

PythonTypeScript

Databases

PostgreSQLClickHouse

Tools

Kafka

Compensation

Pay and benefits.

Base·USD 253,000 – 316,000

Equity·Stock options

Benefits

  • Hybrid Work Model

    Flexible work arrangement with in-office collaboration on Mondays, Tuesdays, and Thursdays

  • Global Team

    Opportunity to work with a diverse, international engineering team

  • Professional Growth

    Continuous learning and development opportunities in cutting-edge software monitoring technologies

  • Equity

    Stock options and potential equity compensation

Process

Interview steps.

  1. 01

    Initial Screening

    HR review of application and resume

  2. 02

    Technical Phone Screen

    Initial discussion with engineering team to assess technical skills and experience

  3. 03

    Technical Interview

    In-depth technical interview focusing on distributed systems, system design, and architectural problem-solving

  4. 04

    System Design Challenge

    Comprehensive system design interview to evaluate candidate's approach to scalable architecture

  5. 05

    Cultural Fit Interview

    Discussion to assess alignment with Sentry's collaborative culture and team values

  6. 06

    Final Executive Interview

    Meeting with senior leadership to discuss strategic vision and candidate's potential impact

Full posting

Original listing.

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. 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 [email protected].

Want to learn more about how Sentry handles applicant data? Get the details in our Applicant Privacy Policy.

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