Staff Software Engineer - Agent Assist

Rippling•San Francisco, CA

About The Position

At Rippling, the Staff Software Engineer will focus on Agent Assist, an AI-powered product area that helps Support representatives answer customer questions faster, more accurately, and with more confidence. This is a high-ownership, lead-shaped role spanning AI, product, systems, and operations. The engineer will work closely with Support and Support Operations to identify pain points, develop product and platform opportunities, and ship improvements that can become durable, reusable AI capabilities across Rippling. The role is hands-on technically while remaining close to operators and customer-facing workflows. The engineer will lead through influence, set technical direction for multiple engineers, and take ambiguous initiatives from operational symptoms through scalable product and platform improvements. Rippling describes the charter as improving Agent Assist for Support representatives, with an open-ended path that the hire will help shape.

Requirements

At least 8 years of software engineering experience.
A strong track record of Staff-level technical leadership and organization-wide impact.
Experience leading complex, multi-engineer or cross-functional initiatives where success required influence rather than direct ownership.
Strong systems thinking and ability to connect frontline operational symptoms to root-cause product, platform, or workflow changes.
Practical AI/LLM fluency, including intuition for context windows, retrieval, tool use, skills, harnesses, evaluations, and tradeoffs in building reliable AI workflows.
Strong product judgment and customer empathy, especially where work has materially improved the day-to-day experience of operators, customers, or internal teams.
Comfort working in ambiguous, fast-moving environments where the 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.

Responsibilities

Own major Agent Assist technical initiatives within Rippling AI, from ambiguous problem discovery through production rollout.
Build AI-powered workflows that help Support representatives answer questions faster, more accurately, and with better context.
Partner with Support, Support Operations, Product, AI Infrastructure, and Engineering to identify high-leverage pain points and turn them into product and platform initiatives.
Observe support workflows, form hypotheses, ship improvements, measure outcomes, and iterate weekly.
Turn repeated support questions, failure modes, and operational workarounds into upstream product and platform fixes.
Design systems that make AI assistance reliable, observable, and controllable in high-stakes customer support workflows.
Build reusable patterns for context, retrieval, tool use, skills, harnesses, and evaluation that can scale beyond Support to broader Rippling AI surfaces.
Lead technical direction for a small group of engineers, including architecture, execution planning, code review, and implementation guidance.
Write production code, debug issues, review critical paths, and make implementation-level tradeoffs.
Mentor senior individual contributors and help teams reason more effectively about AI-native product development.