Senior Software Engineer, Billing Platform

Segment (Twilio); Toronto; On-site; CAD 200,000 - 295,000; Full time

Benefits offered by this job

Equity grants

Paid time off

Group health insurance coverage

Job summary

Sentry is seeking a Senior Software Engineer in Toronto, Ontario to architect and scale their billing infrastructure. This role encompasses the design and implementation of a usage tracking pipeline, ensuring financial-grade accuracy while processing large volumes of events. Candidates should have experience in high-stakes systems and a commitment to mentoring peers.

The expected salary range is between $200,000 and $295,000 CAD, with additional benefits including incentive compensation and health insurance.

Qualifications

• Experience in building or improving systems for financial correctness.
• Ability to mentor engineers through complex projects.
• Experience in operating reliable services with uptime requirements.

Responsibilities

• Architect and scale core systems for billing infrastructure.
• Collaborate on building Sentry’s usage tracking pipeline.
• Design flexible pricing models for diverse billing needs.

Skills

Systems with high-stakes accuracy requirements

Mentorship of engineers

Operational services reliability

Job description

About Sentry

Software runs the world and the pace is faster than ever. Sentry helps developers fix errors and performance issues before users notice, so teams can spend less time firefighting and more time building.

Trusted by 200,000+ organizations, Sentry is today’s application monitoring standard and our team is building its AI-native future.

About the team

The Billing team sits at the intersection of product, finance, and infrastructure. They're responsible for ensuring every observable event—errors, logs, traces, tokens—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 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.

You'll 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 with high-stakes accuracy requirements.

• Mentored engineers through ambiguous, high-stakes projects.

• Operated services where reliability includes uptime and also financial correctness.

The base salary range (or hourly wage range, if applicable) that Sentry reasonably expects to pay for this position is $200,000 to $295,000 CAD. 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 [e-mail].

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