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.It brings together all of the workforce systems that are normally scattered across a company, like payroll, expenses, perks, and computers.

For the first time ever, you can manage and automate every part of the employee lifecycle in a single system. 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.

About The Role This Staff/Principal-level Designer will drive AI-powered design system work at Rippling - from AI user experience patterns to internal systems that drive quality and speed.

The Rippling Design

System team is responsible for driving the core UX across over 40 products and raising the bar for quality across the company. This group is at the forefront of creating cutting edge AI tooling to ensure designers and product teams can build advanced prototypes and production-ready code that leverage our design system code and best practices.

Because Design

Systems is at the heart of the Rippling Platform, this is one of the highest-impact positions at Rippling. As a Lead Designer, you'll work with many teams across Rippling to drive key, platform-wide projects. Defining what great AI-first user experiences look like and ensure those experiences are adopted across our products. Adopt a "shipping beats demos beats memos" mindset.

Set a current bar for UX quality: Lead important platform-wide efforts to build easy-to-use, highly repeatable UX patterns. Drive the future Rippling’s design language,



setting standards for our design system and how systems thinking is embedded within Rippling’s design practice.

Provide design feedback at scale: Build and drive systems that ensure high quality user experience across Rippling draft PRDs and data models; and deliver visuals andspecifications for your final design solutions. 8+ years of product design or design systems experience, heavily indexing on dense B2B platforms, horizontal architectures, or complex developer tooling ~ Active use of LLMs (Claude, ChatGPT) and AI-assisted coding/prototyping tools (Cursor, Claude Code) in your daily workflow. A proven ability to negotiate the horizontal complexity of a compound platform and build UI/UX frameworks that scale cleanly across dozens of product surfaces. ~ An outstanding portfolio showcasing a depth of knowledge in user experience, interaction, and visual/user interface design. ~ Comfort acting as an autonomous IC who drives high-quality craft without becoming a process bottleneck or committee coordinator. ~ 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. Rippling highly values having employees working in-office to foster a cooperative 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 market-competitive salary + benefits + equity.

📌 Product Design Lead, Design Systems (Toronto)
🏢 Rippling
📍 Toronto