Rippling needs to evolve its software foundation to leverage AI for simpler business operations, policy building, and data investigation, addressing increasing complexity and edge cases in managing businesses.
Requirements
- Familiarity with the state of the art in AI development (LLMs, embeddings/vector search, RAG, tool/agent orchestration, evaluation/observability, safety/privacy), plus the curiosity to keep learning as the field evolves.
- Demonstrated high‑level competence in AI‑enabled workflows—designing the interplay of deterministic systems and probabilistic models, modeling failure states and recovery, and creating transparent, user‑controllable experiences.
- Proven ability to think in systems and simplify complexity, ideally with experience designing in challenging or compliance‑heavy environments.
- A strong eye for visual and interaction craft; conversation design and UX writing skills are a plus.
- Design the end‑to‑end Search & AI experience at Rippling—from universal search to embedded assistants—crafting systems that are fast, reliable, explainable, and radically simple.
- Build reusable capabilities and systems—ranking and filtering, prompt governance, evaluation frameworks, and UI components—that scale across Rippling’s product suite.
- Partner deeply with Product, Engineering, Applied ML, and GTM to scope, prototype, and ship new functionality; run iterative experiments, define success metrics, and incorporate offline/online evals into the design process.
Responsibilities
- Design the end‑to‑end Search & AI experience at Rippling—from universal search to embedded assistants—crafting systems that are fast, reliable, explainable, and radically simple.
- Anticipate future needs and edge cases, designing for global scale, strict permissioning, and compliance—while defining clear guardrails, fallbacks, and human‑in‑the‑loop patterns.
- Build reusable capabilities and systems—ranking and filtering, prompt governance, evaluation frameworks, and UI components—that scale across Rippling’s product suite.
- Partner deeply with Product, Engineering, Applied ML, and GTM to scope, prototype, and ship new functionality; run iterative experiments, define success metrics, and incorporate offline/online evals into the design process.
- Deliver high‑fidelity designs and interaction prototypes (including conversation flows) that make complex concepts crystal‑clear to stakeholders and, most importantly, to end users.
- Lead the design of a unified Search & AI platform that powers discovery and assistance across Rippling.
- Craft platform primitives—prompt and safety controls, evaluation loops, and reusable UI—that product teams can plug into seamlessly, while building customer‑facing experiences that are polished, explainable, and auditable.
Other
- A portfolio of complex, high‑impact products delivered from initial concept through iteration and launch; we care more about craft and outcomes than years in seat. Confident candidates with strong portfolios are encouraged to apply—even without a traditional years‑of‑experience profile.
- Get close to customers to understand real workflows, identify where search and AI can remove friction or create leverage, and turn those insights into strategic design priorities that drive measurable impact.
- Excellent communication and storytelling skills—you write clearly, align cross‑functional partners, and can articulate trade‑offs and rationale to executives and engineers alike.
- Rippling 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.
