Staff Software Engineer Jobs in Chicago, IL

About Rippling

Rippling gives businesses one place to run HR, IT, and Finance. It brings together all of the workforce systems that are normally scattered across a company, like payroll, expenses, benefits, and computers. For the first time ever, you can manage and automate every part of the employee lifecycle in a single system.

Take onboarding, for example. With Rippling, you can hire a new employee anywhere in the world and set up their payroll, corporate card, computer, benefits, and even third-party apps like Slack and Microsoft 365—all within 90 seconds.

Based in San Francisco, CA, Rippling has raised $1.4B+ from the world’s top investors—including Kleiner Perkins, Founders Fund, Sequoia, Greenoaks, and Bedrock—and was named one of America's best startup employers by Forbes.

We prioritize candidate safety. Please be aware that all official communication will only be sent from @Rippling.com addresses.

About the payroll calculation team

Payroll is one of the most mission-critical systems a company runs. It has to be correct, compliant, explainable, scalable, and trusted by every employee who depends on it. At Rippling, payroll is also one of our biggest product and engineering frontiers: we’re expanding upmarket to serve much larger companies, scaling internationally across new jurisdictions, and rebuilding core calculation infrastructure for a future where payroll is more automated, transparent, and intelligent.

The Payroll Calculation team owns the systems that determine earnings, deductions, taxes, loans, garnishments, pensions, contributions, and jurisdiction-specific payroll logic. These systems sit at the intersection of distributed systems, product engineering, compliance, data modeling, and customer experience. A great payroll calculation platform does more than produce the right number; it helps admins and internal teams understand why that number is right.

As Rippling serves larger enterprise customers and expands native payroll into more countries, the team is building the technical foundation for payroll at global scale. That means designing calculation frameworks that are configurable, versioned, auditable, debuggable, and explainable, while evolving the architecture to support dramatically more volume and complexity.

We’re looking for a Staff Software Engineer to help lead this work. This is a hands-on technical leadership role for an engineer who wants to build mission-critical systems, set architectural direction, develop exceptional teams, and make payroll accurate, understandable, and dependable at global scale.

What you will do

• Lead architecture and technical strategy for Rippling’s payroll calculation systems.
• Write critical production code and lead from the front on high-impact technical initiatives.
• Design frameworks that make payroll logic configurable, versioned, testable, explainable, scalable, and easy to debug.
• Leverage AI to make payroll logic easier to build, validate, explain, and operate, without compromising accuracy, auditability, or control.
• Build systems that support enterprise-scale payroll for large employers with complex legal-entity structures and approval workflows.
• Help expand Rippling’s native payroll capabilities across new countries and jurisdictions.
• Drive improvements in distributed systems, database performance, caching, reliability, and operability.
• Partner cross-functionally with product, design, payroll operations, HRIS, and other engineering teams to deliver end-to-end customer outcomes.
• Mentor senior and mid-level engineers across payroll calculation areas such as platform, earnings, deductions, taxes, and jurisdiction-specific logic.

What you will need

• Staff-level experience designing and scaling complex production systems where correctness and auditability are critical.
• Strong engineering fundamentals across architecture, data modeling, distributed systems, databases, caching, and reliability.
• A track record of setting technical direction and leading complex initiatives across multiple teams.
• Strong product judgment and the ability to connect platform decisions to customer outcomes.
• Excellent communication skills and comfort driving alignment across engineering, product, and non-technical stakeholders.
• Ability to thrive in a fast-paced environment where priorities and requirements evolve quickly.
• Payroll experience is helpful but not required. We value engineers who have worked on other high-integrity domains where correctness, auditability, and customer trust are essential.

Additional Information

Rippling is an equal opportunity employer. We are committed to building a diverse and inclusive workforce and do not discriminate based on race, religion, color, national origin, ancestry, physical disability, mental disability, medical condition, genetic information, marital status, sex, gender, gender identity, gender expression, age, sexual orientation, veteran or military status, or any other legally protected characteristics, Rippling is committed to providing reasonable accommodations for candidates with disabilities who need assistance during the hiring process. To request a reasonable accommodation, please email accommodations@rippling.com

This role will receive a competitive salary + benefits + equity. The salary for US-based employees will be aligned with one of the ranges below based on location; see which tier applies to your location here.

A variety of factors are considered when determining someone’s compensation–including a candidate’s professional background, experience, and location. Final offer amounts may vary from the amounts listed below.