Top Benefits
About the role
Who you are
- Built or significantly improved systems that handle financial data or high-stakes accuracy requirements—billing systems, payment processing, accounting platforms, or financial data pipelines
- Mentored engineers through ambiguous, high-stakes projects
- Operated services where reliability includes uptime and also financial correctness
- You will love this job if you
- Want to solve the "easy to explain, hard to build" problems—like ensuring a customer's bill matches their usage perfectly, even when processing hundreds of billions of events daily across distributed systems
- Thrive on constraints that force elegant design: financial accuracy is non-negotiable, customer trust depends on billing transparency, and the system must scale with Sentry's user and product growth without rearchitecting every year
- Enjoy partnering across the organization—from BizOps and sales to marketing and leadership—where your code directly impacts ARR and your architectural decisions show up in board-level metrics
- Not sure if you meet 100% of the qualifications? We encourage you to apply anyway. We're interested in people are excited about this opportunity and eager to grow
What the job involves
- The Billing & Revenue engineering team sits at the intersection of product, finance, and infrastructure
- They're responsible for ensuring every observable event—errors, logs, traces, session replays—gets accurately measured, priced, and billed
- Their work directly impacts company revenue and customer trust, requiring distributed systems expertise, attention to financial accuracy, and deep understanding of product usage patterns
- The team works cross-functionally with product, engineering, BizOps, marketing, and sales to build systems that enable new products and pricing models
- As a Senior Software Engineer, you will architect and scale the core systems that power Sentry's billing infrastructure, ensuring accuracy and reliability at massive scale
- You will collaborate on building the next generation of Sentry’s usage tracking pipeline, processing hundreds of billions of events daily with low latency and financial-grade accuracy
- You will help design flexible pricing primitives that support everything from per-event usage billing to complex enterprise contracts, enabling product and sales teams to experiment rapidly while maintaining revenue accuracy and reduced time-to-market for new products
- You will contribute to technical decisions on data consistency challenges unique to billing—like handling event delays, retroactive pricing changes, and distributed count reconciliation across our infrastructure
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
Not the right fit? Search for Software Engineer jobs in Toronto
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.
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Top Benefits
About the role
Who you are
- Built or significantly improved systems that handle financial data or high-stakes accuracy requirements—billing systems, payment processing, accounting platforms, or financial data pipelines
- Mentored engineers through ambiguous, high-stakes projects
- Operated services where reliability includes uptime and also financial correctness
- You will love this job if you
- Want to solve the "easy to explain, hard to build" problems—like ensuring a customer's bill matches their usage perfectly, even when processing hundreds of billions of events daily across distributed systems
- Thrive on constraints that force elegant design: financial accuracy is non-negotiable, customer trust depends on billing transparency, and the system must scale with Sentry's user and product growth without rearchitecting every year
- Enjoy partnering across the organization—from BizOps and sales to marketing and leadership—where your code directly impacts ARR and your architectural decisions show up in board-level metrics
- Not sure if you meet 100% of the qualifications? We encourage you to apply anyway. We're interested in people are excited about this opportunity and eager to grow
What the job involves
- The Billing & Revenue engineering team sits at the intersection of product, finance, and infrastructure
- They're responsible for ensuring every observable event—errors, logs, traces, session replays—gets accurately measured, priced, and billed
- Their work directly impacts company revenue and customer trust, requiring distributed systems expertise, attention to financial accuracy, and deep understanding of product usage patterns
- The team works cross-functionally with product, engineering, BizOps, marketing, and sales to build systems that enable new products and pricing models
- As a Senior Software Engineer, you will architect and scale the core systems that power Sentry's billing infrastructure, ensuring accuracy and reliability at massive scale
- You will collaborate on building the next generation of Sentry’s usage tracking pipeline, processing hundreds of billions of events daily with low latency and financial-grade accuracy
- You will help design flexible pricing primitives that support everything from per-event usage billing to complex enterprise contracts, enabling product and sales teams to experiment rapidly while maintaining revenue accuracy and reduced time-to-market for new products
- You will contribute to technical decisions on data consistency challenges unique to billing—like handling event delays, retroactive pricing changes, and distributed count reconciliation across our infrastructure
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
Not the right fit? Search for Software Engineer jobs in Toronto
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.