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
Brasil