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Rippling is building an autonomous operating system for work, bringing together HR, IT, and Finance into a single platform. You'll join Rippling AI as a Staff Software Engineer focused on Agent Assist, an AI-powered product that helps support representatives answer customer questions faster, more accurately, and with greater confidence.
This is a high-ownership, technically-led role spanning AI, product, systems, and operations. You'll identify real pain points in Support and Support Operations workflows, translate them into product and platform opportunities, and ship improvements that compound across Rippling AI. This is neither a narrow infrastructure role nor pure product engineering—you'll be deeply hands-on technically while staying close to operators and customer-facing workflows.
You'll build a tight feedback loop with Support and Support Ops teams: understand where representatives struggle, form hypotheses, ship quickly, measure impact, and generalize successful patterns into durable AI platform capabilities. You'll lead through influence, set technical direction for multiple engineers, and drive ambiguous work from operational symptoms to scalable product improvements.
Key responsibilities include owning major technical initiatives for Agent Assist from problem discovery through production rollout; building AI-powered workflows that enhance support rep effectiveness; partnering with Support, Product, AI Infrastructure, and Engineering to identify high-leverage pain points; creating rapid operating loops to observe, hypothesize, ship, measure, and iterate; converting repeated support questions and failure modes into upstream fixes; designing systems that make AI assistance reliable, observable, and controllable in high-stakes workflows; building reusable patterns for context, retrieval, tool use, skills, harnesses, and evaluation that scale beyond Support; leading technical direction for a small group of engineers; staying hands-on in the codebase; and mentoring senior individual contributors.
Rippling has raised $1.4B+ from top-tier investors including Kleiner Perkins, Founders Fund, Sequoia, Greenoaks, and Bedrock, and was named one of America's best startup employers by Forbes.
REQUIREMENTS:
- 8+ years of software engineering experience with a strong track record of Staff-level technical leadership and org-wide impact
- Experience leading complex, multi-engineer or cross-functional initiatives requiring influence rather than direct ownership
- Strong systems thinking: ability to reason from frontline operational symptoms to root-cause product, platform, or workflow changes
- Practical AI/LLM fluency, including strong intuition for context windows, retrieval, tool use, skills, harnesses, evaluations, and tradeoffs in building reliable AI workflows
- Strong product judgment and customer empathy, especially in environments where your work materially improved day-to-day experience of operators, customers, or internal teams
- Comfort operating in ambiguous, fast-moving environments where roadmap evolves with technology, product, and user needs
- Clear, precise communication with technical and non-technical stakeholders
- Ability to lead senior engineers, align cross-functional teams, and make progress without perfect ownership boundaries
