itjobs.ca Logo
Sentry logo

Senior Software Engineer (Billing)

Sentryabout 20 hours ago
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

About Sentry

Insurance