Senior Software Engineer, Billing
WFA Digital Insight
As the demand for digital skills continues to grow, Sentry is seeking a Senior Software Engineer to lead the development of their billing infrastructure. With the global remote workforce expanding rapidly, companies are looking for experts who can handle complex systems and high-stakes accuracy requirements. The market for skilled software engineers grew 27% in 2025, and Sentry is poised to lead the charge. Before applying, candidates should know that this role requires a unique blend of technical expertise and collaboration skills, making it an exciting opportunity for those eager to grow in the industry.
Job Description
About the Role
The Senior Software Engineer, Billing will be responsible for architecting and scaling the core systems that power Sentry's billing infrastructure. This role sits at the intersection of product, finance, and infrastructure, requiring a deep understanding of distributed systems, financial accuracy, and product usage patterns. As part of the Billing & Revenue engineering team, you will collaborate with cross-functional teams to build systems that enable new products and pricing models.Day-to-day, you will work on designing flexible pricing primitives, ensuring accuracy and reliability at massive scale, and contributing to technical decisions on data consistency challenges. Your code will directly impact company revenue and customer trust, making this a high-visibility role with significant growth opportunities.
Sentry's Billing & Revenue team is committed to building systems that support the company's growth and customer needs. As a Senior Software Engineer, you will play a critical role in shaping the company's billing infrastructure and ensuring that it meets the highest standards of accuracy and reliability.
What You Will Do
- Collaborate on building the next generation of Sentry's usage tracking pipeline, processing hundreds of billions of events daily
- Design flexible pricing primitives that support various pricing models, from per-event usage billing to complex enterprise contracts
- Contribute to technical decisions on data consistency challenges unique to billing, such as handling event delays and retroactive pricing changes
- Architect and scale the core systems that power Sentry's billing infrastructure, ensuring accuracy and reliability at massive scale
- Work with cross-functional teams, including product, engineering, BizOps, marketing, and sales, to build systems that enable new products and pricing models
- Ensure that the billing system meets the highest standards of financial accuracy and customer trust
- Develop and maintain technical documentation for the billing system
- Participate in code reviews and ensure that the codebase is maintainable, scalable, and follows best practices
What We Are Looking For
- 5+ years of experience in software engineering, with a focus on building scalable and accurate billing systems
- Experience with distributed systems, financial data processing, and high-stakes accuracy requirements
- Strong understanding of programming languages, such as Java, Python, or C++
- Experience with cloud-based infrastructure, such as AWS or Google Cloud
- Strong collaboration and communication skills, with the ability to work with cross-functional teams
- Experience with agile development methodologies and version control systems, such as Git
- Strong problem-solving skills, with the ability to analyze complex problems and develop creative solutions
Nice to Have
- Experience with machine learning or data science, particularly in the context of billing and revenue management
- Knowledge of financial regulations and compliance, such as SOX or PCI-DSS
- Experience with DevOps practices, such as continuous integration and continuous deployment
Benefits and Perks
- Competitive salary range, with a base salary of $200,000 to $295,000 CAD
- Comprehensive benefits package, including health, dental, and vision insurance
- Generous paid time off policy, with flexible work arrangements
- Opportunity to work with a talented and diverse team of engineers and professionals
- Professional development opportunities, including training and conference sponsorships
- Access to cutting-edge technologies and tools, with a focus on innovation and experimentation
How to Stand Out
- Be prepared to discuss your experience with distributed systems and high-stakes accuracy requirements, and how you have handled complex technical challenges in the past.
- Showcase your ability to collaborate with cross-functional teams, including product, engineering, and finance, and highlight your experience with agile development methodologies.
- Emphasize your understanding of financial regulations and compliance, and your experience with cloud-based infrastructure and DevOps practices.
- Prepare to walk through your approach to designing and implementing scalable billing systems, and be ready to discuss your experience with programming languages and data processing.
- Don't be afraid to ask about the company culture and values, and be prepared to discuss how you can contribute to the team's growth and success.
- Be sure to research the company's products and services, and be prepared to discuss how you can apply your skills and experience to drive business growth and revenue.
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