Staff Software Engineer (Issue Workflow)
Top Benefits
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
- 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
Benefits
- Competitive Compensation + Equity
- 401k Plan
- Medical, Dental, Vision Insurance
- Commuter Stipend
- Professional Development Stipend
- Health & Wellness Benefits
- Charitable Matching Program
- Flexible PTO
- Paid Parental Leave- 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
- 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
- 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
- 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
Not the right fit? Search for Software Engineer jobs in Toronto, Ontario, Canada {{REMOTE}}
About Sentry
Your business. Your employees. Your peace of mind. At Sentry, we understand what matters most to you. Because we've spent the last 120 years building trust with our customers—one conversation at a time. We got our start in 1904, when members of the Wisconsin Retail Hardware Association formed their own insurance company. Our dedication to personalized service—and to honoring our Midwestern roots—has helped make Sentry part of one of the largest and most financially secure mutual insurance groups in the United States. Our customers work in a wide range of industries, including transportation, manufacturing, metalworking, construction, auto dealerships, and more. Many of them have been with us for decades. From 401(k) plans and general liability, to commercial property and workers’ compensation, we offer solutions that can help protect your business and your employees. We are headquartered in Stevens Point, Wisconsin, and have offices located across the United States. With more than $25 billion in assets, an $8 billion* policyholder surplus, and an A+ (superior) rating from AM Best,** the industry’s leading rating authority, we can help provide you peace of mind. To learn more about us, the industries we serve, and the products we offer, visit sentry.com. The content provided here is for informational purposes only: https://www.sentry.com/footer/legal-disclaimer. *Assets and policyholder surplus are as of December 31, 2023, and represent the aggregate total for all members of the Sentry Insurance Group and are not reflective of any individual underwriting company. https://www.sentry.com/-/media/sentry-insurance/home/about-us/annual-report-2023/2023-sentry-year-in-review.ashx **Sentry has an AM Best Financial Strength Rating (FSR) of A+ (superior), current as of June 2024. For details about AM Best’s rating scale, see ambest.com/ratings/guide.pdf.
Similar Jobs
Staff Software Engineer (Issue Workflow)
Top Benefits
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
- 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
Benefits
- Competitive Compensation + Equity
- 401k Plan
- Medical, Dental, Vision Insurance
- Commuter Stipend
- Professional Development Stipend
- Health & Wellness Benefits
- Charitable Matching Program
- Flexible PTO
- Paid Parental Leave- 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
- 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
- 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
- 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
Not the right fit? Search for Software Engineer jobs in Toronto, Ontario, Canada {{REMOTE}}
About Sentry
Your business. Your employees. Your peace of mind. At Sentry, we understand what matters most to you. Because we've spent the last 120 years building trust with our customers—one conversation at a time. We got our start in 1904, when members of the Wisconsin Retail Hardware Association formed their own insurance company. Our dedication to personalized service—and to honoring our Midwestern roots—has helped make Sentry part of one of the largest and most financially secure mutual insurance groups in the United States. Our customers work in a wide range of industries, including transportation, manufacturing, metalworking, construction, auto dealerships, and more. Many of them have been with us for decades. From 401(k) plans and general liability, to commercial property and workers’ compensation, we offer solutions that can help protect your business and your employees. We are headquartered in Stevens Point, Wisconsin, and have offices located across the United States. With more than $25 billion in assets, an $8 billion* policyholder surplus, and an A+ (superior) rating from AM Best,** the industry’s leading rating authority, we can help provide you peace of mind. To learn more about us, the industries we serve, and the products we offer, visit sentry.com. The content provided here is for informational purposes only: https://www.sentry.com/footer/legal-disclaimer. *Assets and policyholder surplus are as of December 31, 2023, and represent the aggregate total for all members of the Sentry Insurance Group and are not reflective of any individual underwriting company. https://www.sentry.com/-/media/sentry-insurance/home/about-us/annual-report-2023/2023-sentry-year-in-review.ashx **Sentry has an AM Best Financial Strength Rating (FSR) of A+ (superior), current as of June 2024. For details about AM Best’s rating scale, see ambest.com/ratings/guide.pdf.