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Staff Software Engineer, Billing

Sentry

Toronto, Ontario, Canada permanent

Posted: February 10, 2026

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Quick Summary

We're looking for a Staff Software Engineer to join our team in Toronto, Ontario, Canada. The ideal candidate will have experience with performance and error monitoring tools and be able to work in a hybrid work model across our global hubs.

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 team

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.

About the role

As a Staff Software Engineer you will be a key technical leader, setting engineering culture and solving tough problems.

• You will architect and build 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 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 lead technical decisions on data consistency challenges unique to billing—like handling event delays, retroactive pricing changes, and distributed count reconciliation across our infrastructure.

• You will establish billing-specific engineering standards across Sentry—defining patterns for usage tracking, financial data modeling, and audit logging that other teams can adopt

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.

To thrive in this role, you have

• Built or significantly improved systems that handle financial data or high-stakes accuracy requirements—billing systems, payment processing, accounting platforms, or financial data pipelines.

• Experience with data modeling — distilling complex business problems into elegant, maintainable schemas

• Mentored engineers through ambiguous, high-stakes projects where technical decisions have direct revenue implications.

• Operated services at Sentry’s scale (millions of events per second) where reliability includes uptime and also financial correctness.

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.

The base salary range (or hourly wage range, if applicable) that Sentry reasonably expects to pay for this position is $253,000 to $316,000 USD. A successful candidate’s actual base salary (or hourly wage) amount will be determined by a variety of relevant factors including, without limitation, the candidate’s work location, education, work and other relevant experience, skills, and job-related knowledge. A successful candidate will be eligible to participate in Sentry’s employee benefit plans/programs applicable to the candidate’s position (including incentive compensation, equity grants, paid time off, and group health insurance coverage). See Sentry Benefits for more details about the Company’s benefit plans/programs.

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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