Staff Software Engineer - Payroll AI

Rippling; Toronto; On-site; CAD 262,000 - 437,000; Full time

Job summary

Rippling is seeking Staff Engineers to redefine global payroll infrastructure and scale our onboarding platform. You will help countries expand rapidly by building AI-native onboarding experiences that leverage LLMs to guide users through diverse tax and payroll configurations with precision.

Our mission is to design an architectural blueprint enabling Rippling’s expansion into new markets, creating reusable platform workflows that simplify country setup while ensuring compliance and data

Qualifications

• Experience designing platform infrastructure for global payroll expansion.
• Experience integrating AI/LLMs into workflows with reliable, deterministic results.
• Strong backend systems design and performance optimization skills.

Responsibilities

• Architect for Global Expansion: build platform infrastructure for deploying payroll into new international markets.
• AI-Driven Workflows: combine LLMs with deterministic code for compliant onboarding experiences.
• Deconstruct Complexity: translate regulatory payroll flows into clean backend systems and smooth UX.
• Scale the Platform: own core components of a massive transactional system for high availability and data integrity.

Skills

Global expansion infrastructure

AI-driven workflows

Backend systems design

Data integrity

Education

BS/MS in Computer Science or related field

Job description

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.

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 Role

Rippling processes over $40 Billion in payroll annually across 83 countries and the Payroll Onboarding team sits at the absolute centre of this global engine. Every time a new business joins Rippling, our systems are what get them up, running, and compliant.

We are hiring Staff Engineers to redefine how global payroll infrastructure scales. Our mission is to move away from heavy, manual implementation and build a radically automated, self-serve onboarding engine. Right now, that means we are building AI-native onboarding experiences leveraging LLMs to conversationally guide users through dense, regional tax and payroll configurations, while pairing them with deterministic backend systems to guarantee flawless data precision.

Crucially, we aren't just building for today's footprint. We are building the architectural blueprint that accelerates Rippling’s expansion into new countries. You will design systems that allow our country expansion teams to spin up payroll in a new market in a fraction of the time, abstracting away local compliance complexities into clean, reusable platform workflows.

What You Will Do

• Architect for Global Expansion: Design and build platform infrastructure that empowers country expansion teams to deploy Rippling Payroll into new international markets with minimal friction.
• AI-Driven Workflows: Merge LLMs with rigid, deterministic code. You will build conversational setup experiences that feel human but execute with 100% mathematical and compliance accuracy.
• Deconstruct Complexity: Translate massive, messy regulatory frameworks and payroll setup flows across dozens of jurisdictions into clean, elegant backend systems and seamless product UX.
• Scale the Platform: Own core pieces of a massive transactional system, optimizing for scale, high availability, and bulletproof data integrity.

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 [e-mail]

Rippling highly values having employees working in-office to foster a collaborative work environment and company culture. For office-based employees (employees who live within a defined radius of a Rippling office), Rippling considers working in the office, at least three days a week under current policy, to be an essential function of the employee's role.

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.

The pay range for this role is:

189,000 - 315,000 USD per year(US San Francisco Bay Area)