Software engineering is undergoing its biggest transformation in decades. AI agents are no longer simply assisting developers—they are becoming active participants in how software is designed, written, tested, reviewed, and deployed. The tools, workflows, and platforms that powered the last generation of software development will not be the same ones that power the next.

We’re looking for a Senior Staff Engineer to help define what that future looks like at Rippling. You will own the architectural direction for how over 1,000 engineers—and increasingly thousands of AI agents—interact with one of the largest and fastest-growing codebases in the industry. You will shape the systems that determine how software gets built across the company, from local development environments and CI/CD pipelines to agent sandboxes, testing infrastructure, repository architecture, and AI-native development workflows.

The decisions you make will influence engineering productivity across 100+ teams and directly affect Rippling’s ability to innovate and ship products faster than any competitor in the market. What does a world-class development environment look like when AI agents generate a significant percentage of production code? How should repositories, build systems, and testing frameworks evolve when humans are no longer the primary interface to a codebase?

How do you maintain velocity across hundreds of teams while preserving architectural coherence? If you’re excited by the chance to shape the future of software development at company scale, we’d love to talk. Define and execute the long-term technical vision for Rippling’s Developer Experience platform Architect the next generation of AI-native engineering workflows across a 1,000+ engineer organization Own and evolve critical development infrastructure, including local and cloud environments, CI/CD systems,



repository architecture, test infrastructure, build systems, and agent execution environments Design systems that allow both engineers and AI agents to safely, reliably, and efficiently develop software at scale Make high-leverage architectural decisions that influence hundreds of engineers and dozens of product organizations Lead large-scale technical transformations that span 100+ teams and millions of lines of code Establish technical standards and patterns that balance developer autonomy with platform consistency Partner closely with Infrastructure, Platform, AI, and Product Engineering leaders to solve company-wide challenges Dive deep into complex systems and codebases when necessary, driving clarity in ambiguous technical situations Mentor senior engineers and raise the technical bar across the organization 10+ years of software engineering experience, including significant experience operating at the Staff or Senior Staff level ~ Deep expertise building and scaling distributed systems in high-growth technology companies ~ Strong backend engineering fundamentals and fluency in modern systems programming and application development ~ Experience shaping architecture and technical strategy across large engineering organizations ~ A track record of leading multi-year,



cross-organizational technical initiatives from inception through execution ~ Strong product intuition and a passion for understanding developer needs and building exceptional developer experiences ~ Experience building platforms, infrastructure, developer tooling, CI/CD systems, or large-scale engineering productivity solutions ~ Exceptional communication and influence skills, with the ability to align senior technical and executive stakeholders ~ Curiosity and excitement about how AI will transform software development over the next decade This role gives you the opportunity to help invent entirely new ways of building software.

You’ll work at the center of Rippling’s engineering organization, shaping the developer experience for more than 1,000 engineers while defining how AI agents integrate into every stage of the software development lifecycle. The systems you build won’t just improve productivity—they’ll fundamentally change how software gets created at Rippling for years to come. 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.

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.

📌 Senior Staff Software Engineer, Infrastructure (Toronto)
🏢 Rippling
📍 Toronto