Staff Software Engineer, Billing

Sentry1 months ago

Location

Toronto, Ontario, Canada

Type

Full Time

Salary

CAD 253,000 – 316,000

Level

Staff

Role

Staff Software Engineer

Posted

Feb 10, 2026

Full TimeStaff

The role

Summary

Sentry is seeking a Staff Software Engineer for their Billing & Revenue engineering team, focusing on designing and implementing complex usage tracking and billing systems that process hundreds of billions of events daily with financial-grade accuracy and scalability.

What you'll do

Usage Tracking Pipeline Architecture: Architect and build next-generation usage tracking pipeline capable of processing hundreds of billions of events daily with low latency and financial-grade accuracy

Pricing System Design: Design flexible pricing primitives supporting diverse billing models from per-event usage to complex enterprise contracts

Technical Leadership: Establish billing-specific engineering standards and lead technical decisions on data consistency challenges

Cross-Functional Collaboration: Partner with product, finance, infrastructure, marketing, and sales teams to build scalable billing systems

What we look for

Technical

Financial Systems ExperienceProven experience building or improving systems handling financial data with high-stakes accuracy requirements

Data ModelingAdvanced skills in distilling complex business problems into elegant, maintainable schemas

Distributed SystemsExpertise in operating high-scale services processing millions of events per second

Education

Computer ScienceBachelor's or equivalent professional experience in software engineering or related technical field

Experience

Senior Engineering LeadershipDemonstrated experience mentoring engineers through complex, high-stakes technical projects

Billing System DesignExtensive background in designing and implementing financial tracking and billing infrastructure

Skills

Required skills

Distributed SystemsDeep understanding of designing scalable, reliable distributed computing architectures

Financial Data ProcessingExpert-level skills in handling complex billing and usage tracking systems

Nice to have

Cloud InfrastructureExperience with modern cloud platforms and scalable infrastructure design

Performance OptimizationAdvanced skills in system performance tuning and efficiency improvements

Compensation & benefits

Salary

CAD 253,000 – 316,000 (annual)

Stock options

Available

Benefits

Hybrid Work Model

Flexible work arrangement with in-office collaboration on Mondays, Tuesdays, and Thursdays

Competitive Compensation

Salary range of $253,000 to $316,000 with potential equity grants

Health Insurance

Comprehensive group health insurance coverage

Growth Opportunities

Work with a well-funded startup solving complex technical challenges

Interview process

1
Initial Screening — Review of resume and initial qualifications
2
Technical Phone Screen — Discussion of technical background and initial problem-solving assessment
3
Technical Interview — In-depth technical evaluation focusing on distributed systems and billing infrastructure design
4
System Design Challenge — Comprehensive assessment of architectural and design skills relevant to billing systems
5
Final Leadership Interview — Meeting with senior technical leadership to assess cultural fit and leadership potential