About the Role

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.

This is not a traditional Developer Experience role. 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 impact of this role is difficult to overstate. 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.

You’ll work on problems that very few companies in the world are facing today:

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- 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?





- How do you create leverage for thousands of engineers through a handful of foundational platform decisions?

If you’re excited by the chance to shape the future of software development at company scale, we’d love to talk.

What You Will Do

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- 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

- Identify and eliminate systemic sources of friction that impact engineering productivity across the company

- 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

What You Will Need

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- 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 contemporary 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

- Solid 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

- Comfort operating in highly ambiguous environments where the right answer has not yet been defined

- 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

Why This Role Is Unique

Most infrastructure roles optimize existing systems.

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 organizati

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