Lead Product Designer - AI Platform

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 $1.4B+ 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 role

Design is at the center of how Rippling turns complex business software into products people can understand, trust, and use. As a Lead Product Designer on the AI Platform team, you will help define how AI shows up across Rippling’s product suite and shape the patterns, systems, and interaction models that make enterprise AI useful, reliable, and deeply integrated into work.

This is a leadership-level individual contributor role for a designer who can operate across ambiguous, high-leverage problem spaces. You will work across multiple product verticals, partnering closely with product, engineering, and executive leadership, aligning others to critical outcomes while helping to translate emerging AI capabilities into coherent product experiences that scale across Rippling. The work is highly visible and strategically important: you will influence not just individual features, but the future of enterprise human-agent interaction.

The right person for this role is both strategic and hands-on. You should be able to shape the narrative for how enterprise AI should work, while also getting deep into the details of interaction and graphic design, technical constraints, model behavior, workflows, permissions, and edge cases. In short: you should care about the interface, but understand that the hard part is often the plumbing behind it. If you are a design leader with a renewed interest in building AI things with AI tools, we want to talk to you.

What you will do

• Define and drive the design vision for AI Platform experiences across Rippling, shaping the product concepts, interaction patterns, and principles that teams use to build AI-native workflows.
• Help establish “how Rippling does AI” by creating reusable frameworks for AI interactions, agentic workflows, automation, human-in-the-loop review, transparency, trust, permissions, and control.
• Lead large, ambiguous, cross-product design initiatives with many dependencies across product, engineering, data, infrastructure, design, and go-to-market teams.
• Partner deeply with AI Platform PMs, engineering managers, product engineers, and design leaders to turn complex technical capabilities into intuitive, trustworthy user experiences.
• Work hands-on with individual pods while also connecting patterns across the broader AI Platform roadmap and adjacent product areas.
• Translate emerging AI behaviors, model capabilities, evaluations, agentic workflows, and platform constraints into practical product patterns that can be adopted across teams.
• Create high-fidelity prototypes, frameworks, written narratives, and decision-making artifacts that align executives, de-risk strategic bets, and help teams move quickly.
• Raise the craft bar for AI product experiences across Rippling by coaching designers, reviewing work, and codifying patterns into scalable guidance.
• Stay close to customers, customer-facing teams, competitors, and frontier AI developments to identify unmet needs and inform Rippling’s long-term AI product strategy.
• Help shape how enterprise AI looks beyond demos: grounded in real business workflows, sensitive data, approvals, accountability, and measurable customer value.

What you will need

• At least 10 years of product design experience, including significant experience designing and shipping complex SaaS, platform, or enterprise products.
• Recent hands-on experience designing and shipping AI products or AI-powered features; you should be fluent in the language, trade-offs, and constraints of modern AI product development.
• Exceptional systems thinking, with the ability to understand and design across complex product architectures, data flows, permissions, dependencies, and edge cases.
• A track record of leading high-impact, cross-product initiatives as a senior IC, principal designer, design director, or equivalent design leader.
• Deep interaction design craft, including the ability to create novel patterns where established conventions do not yet exist and to prove those patterns through prototypes or production work.
• Strong product judgment and strategic thinking, with the ability to frame ambiguous problems, identify high-leverage opportunities, and influence roadmaps across multiple teams.
• Excellent executive communication, storytelling, writing, and documentation skills; you should be able to make complex ideas crisp, persuasive, and actionable for senior leaders and cross-functional teams.
• Technical curiosity and fluency, including comfort working closely with engineers on AI systems, platform primitives, model behavior, evals, agentic workflows, MCPs, or related technical concepts.
• A bias toward shipping, learning, and iterating quickly without sacrificing quality, coherence, or user trust.
• A collaborative leadership style that builds trust across design, product, engineering, GTM, and customer-facing teams, while constructively challenging assumptions and raising the bar.
• A strong point of view on how AI should improve enterprise software, paired with the humility to learn from customers, data, technical constraints, and the teams closest to implementation.

If you don't meet every requirement but are excited about the role, we encourage you to apply. Skills transfer in unexpected ways, and diverse perspectives often lead to the most innovative solutions.

About the team

The AI Platform team is building the foundations that make Rippling’s products AI-native. The team works across the full Rippling platform, partnering with product teams in areas like HR, IT, Finance, Spend, Travel, Payroll, Benefits, and more to bring AI capabilities into the workflows businesses rely on every day.

This team sits at the intersection of product design, AI infrastructure, product engineering, and company strategy. The work is unusually broad: designing AI patterns that can operate across many domains, many user types, and many product surfaces while still feeling coherent, trustworthy, and distinctly Rippling.

As the Lead Product Designer for AI Platform, you will be a key design partner to senior product and engineering leaders and a force multiplier for designers working on AI experiences across the company. You will engage with PMs and EMs across AI Platform, go deep with pods that are actively shipping, and help connect their work into a clear, scalable product language for AI at Rippling.

Even if you don’t meet all of the requirements listed here, we still encourage you to apply. Skills can be used in lots of different ways, and your life and professional experience may be relevant beyond what a list of requirements will capture.

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 [email protected]

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.

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.

[{'location': 'US Tier 1', 'currency': 'USD', 'frequency': 'YEAR', 'rangeStart': 174000.0, 'rangeEnd': 325000.0, 'isRemote': False}, {'location': 'US Tier 2', 'currency': 'USD', 'frequency': 'YEAR', 'rangeStart': 156600.0, 'rangeEnd': 292500.0, 'isRemote': False}, {'location': 'US Tier 3', 'currency': 'USD', 'frequency': 'YEAR', 'rangeStart': 147900.0, 'rangeEnd': 276250.0, 'isRemote': False}]