Senior Software Engineer, Billing
WFA Digital Insight
As the demand for skilled software engineers continues to rise, with a 25% increase in remote job postings in 2025, Sentry's Senior Software Engineer role stands out. This position requires a unique blend of technical expertise and financial acumen, making it an exciting opportunity for those looking to challenge themselves. With the global remote work trend on the rise, companies like Sentry are at the forefront, offering hybrid work models that foster collaboration and innovation. Before applying, candidates should be aware that this role demands a deep understanding of distributed systems and financial accuracy, as well as the ability to mentor engineers and operate high-stakes services.
Job Description
About the Role
Sentry, a leading provider of performance and error monitoring tools, is seeking an experienced Senior Software Engineer to join their Billing and Revenue engineering team. As a key member of this team, you will be responsible for architecting and scaling the core systems that power Sentry's billing infrastructure, ensuring accuracy and reliability at massive scale. The Billing and Revenue team sits at the intersection of product, finance, and infrastructure, making this role a unique opportunity to work cross-functionally with various teams.The Senior Software Engineer 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. This role requires a deep understanding of distributed systems, financial accuracy, and product usage patterns, as well as the ability to design flexible pricing primitives that support everything from per-event usage billing to complex enterprise contracts.
What You Will Do
- 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
- Design flexible pricing primitives that support everything 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, retroactive pricing changes, and distributed count reconciliation across infrastructure
- Architect and scale the core systems that power Sentry's billing infrastructure, ensuring accuracy and reliability at massive scale
- Partner with cross-functional teams, including product, engineering, BizOps, marketing, and sales, to build systems that enable new products and pricing models
- Mentor engineers through ambiguous, high-stakes projects
- Operate services where reliability includes uptime and financial correctness
- Ensure customer trust through billing transparency and revenue accuracy
- Collaborate with the product team to experiment rapidly while maintaining revenue accuracy and reduced time-to-market for new products
- Contribute to the development of systems that handle financial data or high-stakes accuracy requirements
What We Are Looking For
- Experience building or significantly improving systems that handle financial data or high-stakes accuracy requirements
- Proficiency in distributed systems and financial accuracy
- Ability to design flexible pricing primitives that support various billing models
- Experience operating services where reliability includes uptime and financial correctness
- Strong mentoring and leadership skills, with experience guiding engineers through high-stakes projects
- Ability to work cross-functionally with various teams, including product, engineering, BizOps, marketing, and sales
- Strong understanding of product usage patterns and ability to contribute to technical decisions on data consistency challenges
- Experience with cloud-based infrastructure and containerization
- Strong problem-solving skills and ability to work in a fast-paced environment
Nice to Have
- Experience with cloud-based billing systems and payment processing
- Knowledge of financial data pipelines and accounting platforms
- Familiarity with agile development methodologies and version control systems
- Experience with security and compliance in a cloud-based environment
Benefits and Perks
- Competitive salary range of 90,000 to $280,000 USD
- Opportunity to participate in Sentry's employee benefit plans and programs
- Hybrid work model with in-office anchor days to encourage collaboration and innovation
- Flexible PTO and vacation days
- Comprehensive health insurance and wellness programs
- Remote work stipend and equipment allowance
- Professional development opportunities and conference sponsorships
- Access to cutting-edge technologies and tools
How to Stand Out
- Be prepared to discuss your experience with distributed systems and financial accuracy, and how you've applied these skills in previous roles.
- Showcase your ability to design flexible pricing primitives and contribute to technical decisions on data consistency challenges.
- Highlight your experience with cloud-based infrastructure and containerization, and your ability to operate services where reliability includes uptime and financial correctness.
- Emphasize your strong problem-solving skills and ability to work in a fast-paced environment, and provide examples of how you've guided engineers through high-stakes projects.
- Be ready to discuss your understanding of product usage patterns and how you can contribute to the development of systems that enable new products and pricing models.
- Don't be afraid to ask about the company culture and values, and how they impact the way the team works and collaborates.
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