In today's conversation, Brett sits down with CMO of Figma, Sheila Joglekar Vashee. Previously the second marketing hire at Dropbox, where she helped scale the company past $1 billion in revenue, she now leads marketing at Figma fresh off its IPO. In an industry that has spent a decade trying to turn marketing into something closer to hedge fund trading, Sheila argues the art was always the point — we just stopped talking about it. She unpacks how to run marketing as a portfolio of moonshots, why giving teams different goals breeds dysfunction, how to scale taste across an organization, and why old playbooks are obsolete, even as the fundamentals hold.

In today's episode, we discuss:

How to run marketing like a portfolio of moonshots
The value of disruptive energy for senior marketers
Why "Ubiquity is the opposite of cool"
How to actually scale taste across an organization
What great marketing looks like in the AI era

Referenced:

Apple: https://www.apple.com/
Dennis Woodside: https://www.linkedin.com/in/dennis-woodside-341302/
Dropbox: https://www.dropbox.com/
Dylan Field: https://www.linkedin.com/in/dylanfield/
Figma: https://www.figma.com
Francoise Brougher: https://www.linkedin.com/in/francoise-brougher-341a72/
Gap: https://www.gap.com/
Google Chrome: https://www.google.com/chrome/
Harley-Davidson: https://www.harley-davidson.com/
HubSpot: https://www.hubspot.com/
Notion: https://www.notion.com/
Opendoor: https://www.opendoor.com/
Pinterest: https://www.pinterest.com/
Square: https://squareup.com/
The Web Is What You Make of It (Dear Sophie): https://www.youtube.com/watch?v=pzOBOuyr-EU
Urban Outfitters: https://www.urbanoutfitters.com/
Yamini Rangan: https://www.linkedin.com/in/yaminirangan/

Where to find Sheila:

LinkedIn: https://www.linkedin.com/in/sheilavashee/
X: https://x.com/sheilavashee

Where to find Brett:

LinkedIn: https://www.linkedin.com/in/brett-berson-9986644/
X: https://x.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 Introduction

00:07 What excellent marketing actually is in 2026

01:36 Why giving teams different goals creates dysfunction

02:36 The most important decision Sheila made as CMO last year

04:26 The real difference between an SVP and a CMO

06:05 Marketing is one engine - not separate pieces

07:15 The tension between brand and growth

09:25 The decisions a CMO should never be making

09:55 Running marketing like a portfolio of moonshots

12:46 "Ubiquity is the opposite of cool"

15:11 Why a few companies get a flywheel of momentum

16:44 The Silicon Valley clock and irrational perception cycles

19:25 How to actually scale taste across an org

21:09 What changes for a CMO in a post-LLM world

23:15 Why the artistic side of marketing never really left

26:05 Whether taste can ever be encoded in software

27:15 Telling an optimistic, yet realistic story about AI

30:50 You need to make people care

32:11 What surprised Sheila about being a public-company CMO

33:46 Why Figma won enterprise where Dropbox couldn't

35:25 Sheila’s favorite campaign ever

37:10 Why announcement videos full of humans, lack humanity

38:55 Playbooks are obselete, but the fundamentals are not

40:25 Why marketing in 2026 demands disruptive energy

41:54 How Sheila architects her week

48:55 Where corporate politics actually come from

53:55 "Sheila, are you going to change the world in this job?"

58:09 What's unique about the CMO and CEO relationship