Figma is not the source of truth | Ryan Lucas (VP of Design, Rippling)

In the second Executive Function episode, Brett sits down with Ryan Lucas, VP of Design at Rippling. Before Rippling, Ryan led design at Retool and co-founded multiple startups, bringing a rare founder's perspective to design leadership. A trained industrial designer, Ryan traces the roots of modern software design back 2,000 years to make the case that products must be useful, usable, and desirable - and above all, used. In today's episode, we discuss: Why design leaders who stop designing stop leading The four pillars every design manager must master How to delegate when you're a perfectionist Why leaders need strong opinions How to scale good judgment What Rippling's operating system teaches about speed and commitments References: Airbnb: https://www.airbnb.com/ Amazon: https://www.amazon.com/ Apple: https://www.apple.com/ Asana: https://www.asana.com/ Brian Chesky: https://www.linkedin.com/in/brianchesky/ CrossFit: https://www.crossfit.com/ Figma: https://www.figma.com/ Honeywell: https://www.honeywell.com/ Liz Sanders: https://www.linkedin.com/in/sandersliz/ Nest: https://store.google.com/category/google_nest Notion: https://www.notion.so/ Parker Conrad: https://www.linkedin.com/in/parkerconrad/ Patrick Collison: https://www.linkedin.com/in/patrickcollison/ Retool: https://retool.com/ Rippling: https://www.rippling.com/ Stripe: https://www.stripe.com/ Where to find Ryan: LinkedIn: https://www.linkedin.com/in/ryanwlucas/ Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps: 00:00 Intro 00:08 What design actually does at a software company 01:40 The roots of design: from industrial design to software 03:29 Useful, usable, desirable — and used 04:49 How design relates to engineering, product, and marketing 08:15 Measuring success as a design leader 12:40 The gap between director and VP-level design leadership 14:23 Why great design leaders jump up and down in altitude 19:26 The four pillars every design manager must master 21:34 Over-indexing on quality and the perfectionist trap 25:11 When lowering the quality bar actually cost the business 27:53 How to build judgment through pattern matching 31:25 How Ryan's design team differs from the rest 34:31 Why Figma is not the source of truth 36:32 How Ryan spends his week: recruiting, crits, and staff meetings 38:39 The "Do/Try/Consider" framework 42:12 The most important decisions of the past year 44:05 Should one-on-ones exist? 46:45 How to scale judgment 50:49 What to look for when hiring your first design leader 54:54 Advice for young designers who want to lead 58:24 Demanding yet supportive: A balanced management style 01:02:43 What Rippling's operating system teaches about execution