Copy of Senior Software Engineer, Billing Platform

Sentry2 days ago

Location

Toronto, Ontario, Canada

Type

Full Time

Salary

CAD 200,000 – 295,000

Level

Senior

Role

Senior Software Engineer

Posted

Jul 1, 2026

Full TimeSenior

The role

Summary

Senior Software Engineer role at Sentry focused on architecting and scaling the billing platform infrastructure. You'll design systems processing hundreds of billions of events daily with financial-grade accuracy, build flexible pricing primitives supporting complex enterprise contracts, and solve distributed systems challenges unique to billing operations. This position requires deep expertise in high-accuracy systems, mentoring capabilities, and cross-functional collaboration with product, finance, and infrastructure teams.

What you'll do

Architect and Scale Billing Infrastructure: Design, build, and maintain core systems that power Sentry's billing platform, ensuring accuracy and reliability while processing hundreds of billions of events daily with low-latency performance and financial-grade correctness at massive scale.

Build Next-Generation Usage Tracking Pipeline: Collaborate on developing the next generation of Sentry's usage tracking infrastructure that handles hundreds of billions of events daily, implementing systems that maintain both low latency and financial-grade accuracy for billing operations.

Design Flexible Pricing Primitives: Engineer extensible pricing systems that support diverse billing models from per-event usage billing to complex enterprise contracts, enabling rapid product and sales experimentation while maintaining revenue accuracy and reduced time-to-market for new offerings.

Solve Distributed Systems Data Consistency Challenges: Contribute technical expertise to address billing-specific data consistency problems including event delay handling, retroactive pricing changes, and distributed count reconciliation across infrastructure to ensure billing accuracy and customer trust.

Cross-Functional Technical Leadership: Collaborate with product, engineering, BizOps, marketing, sales, and leadership teams to translate business requirements into technical architecture decisions that directly impact annual recurring revenue (ARR) and influence board-level company metrics.

Mentor Engineers on Complex Projects: Guide and mentor engineering team members through ambiguous, high-stakes projects involving financial accuracy requirements, building team capability in billing systems and distributed systems architecture.

Ensure Financial Correctness and Operational Reliability: Operate and maintain services where reliability encompasses both uptime and financial correctness, ensuring customer bills match usage perfectly even when processing massive event volumes across distributed infrastructure.

What we look for

Technical

Distributed Systems ArchitectureDemonstrated expertise designing and building distributed systems at scale, particularly experience with handling consistency challenges, event processing pipelines, and reconciliation across infrastructure.

High-Accuracy Financial SystemsExperience building or significantly improving systems with high-stakes accuracy requirements where financial correctness is non-negotiable and directly impacts customer trust and company revenue.

Large-Scale Data ProcessingProven ability to architect systems processing massive event volumes with low-latency performance, including usage metering, event tracking, or similar high-throughput data pipeline experience.

Cloud Infrastructure and ScalabilityExperience operating and scaling services in cloud environments, managing infrastructure that grows with user base and product expansion without requiring annual rearchitecting.

Database Design and OptimizationStrong foundation in database selection, schema design, and query optimization for systems requiring both consistency guarantees and high throughput at scale.

Education

Bachelor's Degree in Computer Science or Related FieldFormal education in Computer Science, Software Engineering, or closely related discipline, or equivalent professional experience demonstrating mastery of computer science fundamentals.

Experience

Senior Software Engineering ExperienceMinimum 5+ years of software engineering experience with at least 2-3 years in senior-level roles involving architectural decisions and technical leadership on complex systems.

Billing or Metering SystemsExperience building or significantly improving billing, usage metering, or related revenue-impacting systems where accuracy and reliability are critical and errors have direct financial consequences.

Team Mentorship and Technical LeadershipDemonstrated track record mentoring engineers through ambiguous, high-stakes projects and making technical decisions that impact organizational metrics and cross-functional initiatives.

Production Systems OperationsExperience operating production services where reliability encompasses both system uptime and business-critical accuracy (financial, compliance, or audit correctness).

Skills

Required skills

Distributed Systems DesignAdvanced capability in designing distributed systems, handling eventual consistency, managing state across multiple services, and solving coordination problems at scale.

Backend Systems ArchitectureExpert-level ability to architect backend systems that scale from millions to billions of requests, making technology choices that balance correctness, performance, and operational burden.

Data Pipeline ArchitectureDeep expertise designing and maintaining high-throughput, low-latency data pipelines that process massive event volumes while maintaining accuracy and supporting complex transformations.

Financial Systems KnowledgeUnderstanding of billing, revenue recognition, pricing models, and the unique operational challenges of systems where financial accuracy is non-negotiable and errors have direct business impact.

Software Design and System ThinkingAbility to design elegant solutions under constraints, think through edge cases in complex systems, and make architectural decisions that balance multiple competing priorities.

Technical Leadership and CommunicationStrong ability to lead technical discussions, mentor other engineers, make architectural decisions collaboratively, and communicate complex technical concepts to non-technical stakeholders.

Nice to have

Open Source ContributionActive participation in open-source projects, particularly those related to observability, monitoring, or infrastructure, demonstrating commitment to building accessible developer tooling.

SaaS and Multi-tenant SystemsExperience building multi-tenant SaaS platforms with complex pricing models, handling customer-specific configurations, and managing billing at scale across diverse customer profiles.

Observability Platform ExperienceBackground working on observability, monitoring, or APM platforms where understanding telemetry data, traces, logs, and events is crucial to system design and business model.

Enterprise Contract Negotiation AwarenessUnderstanding of how complex enterprise contracts, seat-based pricing, volume discounts, and custom billing arrangements influence technical system design and flexibility requirements.

Event Sourcing or CQRS PatternsExperience with event sourcing architecture or Command Query Responsibility Segregation patterns for maintaining complex state and supporting audit trails in mission-critical systems.

Compensation & benefits

Salary

CAD 200,000 – 295,000 (annual)

Stock options

Available

Benefits

Equity Grants

Participate in Sentry's equity grant program, allowing you to share in company growth and success as an employee shareholder.

Paid Time Off

Competitive paid time off policy supporting work-life balance and enabling time for rest and professional development.

Comprehensive Group Health Insurance

Group health insurance coverage including medical, dental, and vision benefits for you and your family.

Incentive Compensation

Performance-based bonus and incentive compensation programs tied to individual and company goals.

Inclusive and Accessible Workplace

Sentry commits to building a diverse, inclusive culture where every teammate can thrive, with accessibility at the forefront of company values and practices.

Reasonable Accommodations

Sentry provides reasonable accommodations for employees and candidates with disabilities, with dedicated support at [email protected].

Interview process

1
Application Review — Initial screening of your background, experience, and resume against the Senior Software Engineer requirements, focusing on distributed systems expertise and billing or high-accuracy systems experience.
2
Recruiter Screening Call — Preliminary conversation with Sentry's recruitment team to discuss your career background, interest in the billing platform role, and high-level technical background before proceeding to engineering interviews.
3
Technical Problem-Solving Interview — Engineering interview focused on distributed systems design, data pipeline architecture, or billing system challenges where you discuss your approach to building accurate, scalable systems.
4
System Design Interview — Deep-dive technical conversation on designing complex systems at scale, including discussing trade-offs in consistency models, architecture decisions for handling billions of events, and ensuring financial accuracy.
5
Team and Cross-Functional Collaboration Discussion — Conversation with members of the billing team or cross-functional partners to evaluate communication style, ability to work across organizational boundaries, and approach to mentoring and technical leadership.
6
Leadership and Mentorship Evaluation — Discussion focusing on your experience mentoring engineers, making decisions through ambiguity, and driving technical initiatives across teams with impact on organizational metrics.
7
Final Round with Leadership — Meeting with engineering leadership or senior team members to discuss your vision for the billing platform, long-term technical strategy, and cultural fit with Sentry's mission around developer tools accessibility.