In Depth

How to build a beloved tech brand | Sheila Joglekar Vashee (CMO, Figma)


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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

            ...more
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