Product Design Lead, AI

About Rippling

Rippling 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 $1.85B+ 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 role

As the Product Design Lead focused on AI, you’ll shape how customers find answers, investigate data, and take action across Rippling. From universal search to AI‑assisted workflows, your work will define how operators, admins, and employees navigate complexity and get to confident outcomes—fast.

Rippling is the software many businesses use to stand up and run their entire operation. With increasing complexity, deterministic nature, and wide variance of edge cases—the foundation of standing up a business will evolve to simpler patterns leveraging AI to help with policy building, data investigation, and the ins and outs of running a business day‑to‑day. We’re looking for a designer with extraordinary craft, deep familiarity and curiosity in the ever‑changing landscape of enterprise AI, and an uncanny ability to envision—and inspire others about—the future.

You’ll lead the design of a unified Search & AI platform that powers discovery and assistance across Rippling. Whether customers are self‑serve SMBs or managed enterprise accounts, searching for a single answer or orchestrating an end‑to‑end workflow, your work will make it simple. You’ll 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. You’ll partner deeply with product teams to blend deterministic systems with probabilistic models, designing graceful fallbacks and human‑in‑the‑loop moments where it matters.

What you will do

• 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.
• 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.
• 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.

What you will need

• 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.
• 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.
• Excellent communication and storytelling skills—you write clearly, align cross‑functional partners, and can articulate trade‑offs and rationale to executives and engineers alike.

If you don't necessarily meet all of these requirements, we still encourage you to apply. Skills transfer in unexpected ways, and diverse perspectives often lead to the most innovative solutions.

Additional Information

Rippling 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 accomodations@rippling.com

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. 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

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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.

The pay range for this role is:

165,000 - 288,750 USD per year (US San Francisco Bay Area)

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Product Design

San Francisco, CA

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