Staff Software Engineer - Agent Assist

About RipplingRippling gives businesses one place to run HR, IT, and Finance. It brings together all of the workforce systems that are normally scattered across a company, like payroll, expenses, benefits, and computers. For the first time ever, you can manage and automate every part of the employee lifecycle in a single system.Take onboarding, for example. With Rippling, you can hire a new employee anywhere in the world and set up their payroll, corporate card, computer, benefits, and even third-party apps like Slack and Microsoft 365—all within 90 seconds.Based in San Francisco, CA, Rippling has raised $1.4B+ from the world’s top investors—including Kleiner Perkins, Founders Fund, Sequoia, Greenoaks, and Bedrock—and was named one of America's best startup employers by Forbes.We prioritize candidate safety. Please be aware that all official communication will only be sent from @Rippling.com addresses.About the roleAt Rippling, we’re building an autonomous operating system for work—and Support is one of the clearest places where AI can make work dramatically better.You’ll be joining Rippling AI as a Staff Software Engineer focused on Agent Assist, the AI-powered product area that helps support reps answer customer questions faster, more accurately, and with more confidence. This is a high-ownership, lead-shaped role for someone who can operate across AI, product, systems, and operations: identifying real Support and Support Operations pain points, turning them into product and platform opportunities, and shipping improvements that compound across Rippling AI.This is not a narrow infrastructure role, and it is not a pure product engineering role. The right person will be deeply hands-on technically while also staying close to operators and customer-facing workflows. You’ll build a tight loop with Support and Support Ops: understand where reps struggle, form hypotheses, ship quickly, measure impact, and generalize the most successful patterns back into durable AI platform capabilities.You’ll be expected to lead through influence, set technical direction for multiple engineers, and drive ambiguous work from messy operational symptoms to scalable product and platform improvements. The charter is concrete—make Agent Assist meaningfully better for Support reps—but the path is intentionally open-ended, and you’ll help shape it.What you will doOwn major technical initiatives for Agent Assist within Rippling AI, from ambiguous problem discovery through production rollout.Build AI-powered workflows that help Support reps answer questions faster, more accurately, and with better context.Partner deeply with Support, Support Operations, Product, AI Infrastructure, and Engineering to identify high-leverage pain points and turn them into product and platform bets.Create a rapid operating loop: observe support workflows, form hypotheses, ship improvements, measure outcomes, and iterate weekly.Convert 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 into broader Rippling AI surfaces.Lead technical direction for a small group of engineers, including architecture, execution planning, code review, and implementation guidance.Stay hands-on in the codebase: write production code, debug issues, review critical paths, and make implementation-level tradeoffs.Raise the engineering bar by mentoring senior ICs and helping teams reason more effectively about AI-native product development.What you will need8+ 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 where success required influence rather than direct ownership.Strong systems thinking: you can 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 the tradeoffs involved in building reliable AI workflows.Strong product judgment and customer empathy, especially in environments where your work materially improved the day-to-day experience of operators, customers, or internal teams.Comfort operating in ambiguous, fast-moving environments where the roadmap evolves as the technology, product, and user needs evolve.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.Additional InformationRippling is an equal opportunity employer. We are committed to building a diverse and inclusive workforce and do not discriminate based on race, religion, color, national origin, ancestry, physical disability, mental disability, medical condition, genetic information, marital status, sex, gender, gender identity, gender expression, age, sexual orientation, veteran or military status, or any other legally protected characteristics, Rippling is committed to providing reasonable accommodations for candidates with disabilities who need assistance during the hiring process. To request a reasonable accommodation, please email View email address on click.appcast.io highly values having employees working in-office to foster a collaborative work environment and company culture. For office-based employees (employees who live within a defined radius of a Rippling office), Rippling considers working in the office, at least three days a week under current policy, to be an essential function of the employee's role.This role will receive a competitive salary + benefits + equity. The salary for US-based employees will be aligned with one of the ranges below based on location; see which tier applies to your location here.A variety of factors are considered when determining someone’s compensation–including a candidate’s professional background, experience, and location. Final offer amounts may vary from the amounts listed below.