Resourcing trade-offs and hard hiring choices

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