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