Staff AI Engineer — Agent Assist & Support

Rippling; New York (NY); On-site; USD 189,000 - 315,000; Full time

Job summary

Rippling is seeking a Staff Software Engineer to lead Agent Assist within Rippling AI. You will work across AI, product, systems, and operations to identify pain points, formulate hypotheses, and ship improvements that scale across the AI platform.

You’ll balance hands-on coding with leadership responsibilities, mentoring engineers and partnering with Support and Ops to deliver reliable, context-rich AI workflows.

Qualifications

• 8+ years software engineering with staff-level leadership experience.
• Ability to drive multi-engineer initiatives through influence.
• Strong systems thinking from operations to product and platform changes.
• Practical AI/LLM fluency and context/tool usage know-how.

Responsibilities

• Own major technical initiatives for Agent Assist within Rippling AI from discovery to production rollout.
• Build AI-powered workflows to help support reps answer questions faster and with better context.
• Collaborate with Support, Support Operations, Product, AI Infrastructure, and Engineering to identify pain points and convert to product bets.
• Lead a small team of engineers, set technical direction, review code, and mentor others.
• Stay hands-on in code, debug critical paths, and balance tradeoffs between speed and quality.

Skills

Staff leadership

Systems thinking

AI/LLM fluency

Cross-functional collaboration

Technical communication

Ambiguity handling

Job description

Rippling is seeking a Staff Software Engineer to lead Agent Assist within Rippling AI. You will work across AI, product, systems, and operations to identify pain points, formulate hypotheses, and ship improvements that scale across the AI platform.

You’ll balance hands-on coding with leadership responsibilities, mentoring engineers and partnering with Support and Ops to deliver reliable, context-rich AI workflows.