Senior Software Engineer (Billing)
Toronto, Ontario, Canada {{REMOTE}}
Senior Level
Full-Time
Top Benefits
Competitive Compensation & Equity
401(k) Retirement Plan
Medical, Dental, Vision Insurance
About the role
- 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- Operated services where reliability includes uptime and also financial correctness
- Mentored engineers through ambiguous, high-stakes projects
- Built or significantly improved systems that handle financial data or high-stakes accuracy requirements—billing systems, payment processing, accounting platforms, or financial data pipelines
- You will love this job if you
- 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
- 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
- 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
- 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