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

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