Senior Staff Engineer — AI-Driven Dev Platform

Rippling; Toronto; On-site; CAD 150,000 - 230,000; Full time

Job summary

Rippling is seeking a Senior Staff Engineer to define the architectural direction for the Developer Experience platform used by over 1,000 engineers. You will help shape how AI agents participate in the software lifecycle, influencing local dev environments, CI/CD, and code repositories.

You will lead multi-team initiatives, collaborate with Infra, Platform, AI, and Product leaders, and mentor senior engineers while maintaining architectural coherence at scale.

Qualifications

• 10+ years of software engineering experience at Staff or Senior Staff level.
• Deep expertise building and scaling distributed systems in high-growth tech environments.
• Strong backend fundamentals and modern systems programming.
• Experience shaping architecture and technical strategy across large teams.
• Track record leading multi-year, cross-organizational technical initiatives.
• Strong product intuition for developer experiences.
• Experience building platforms, infrastructure, developer tooling, CI/CD systems.
• Comfort in ambiguous environments with evolving requirements.
• Exceptional communication and influence with senior stakeholders.
• Curiosity about how AI will transform software development.

Responsibilities

• Define and execute the long-term technical vision for Rippling’s Developer Experience platform.
• Architect the AI-native engineering workflows for a large, distributed organization.
• Own and evolve critical development infrastructure: local and cloud environments, CI/CD, repository architecture, test infra, build systems, and agent execution environments.
• Design systems enabling engineers and AI agents to develop software safely and efficiently at scale.
• Lead high-leverage architectural decisions impacting hundreds of engineers and multiple product teams.
• Mentor senior engineers and raise the technical bar across the organization.

Skills

Distributed systems

Backend engineering

Architecture leadership

Cross-organizational initiatives

Developer experience

AI/ML awareness

CI/CD tooling

Communication skills

Tools

CI/CD systems

Job description

Rippling is seeking a Senior Staff Engineer to define the architectural direction for the Developer Experience platform used by over 1,000 engineers. You will help shape how AI agents participate in the software lifecycle, influencing local dev environments, CI/CD, and code repositories.

You will lead multi-team initiatives, collaborate with Infra, Platform, AI, and Product leaders, and mentor senior engineers while maintaining architectural coherence at scale.