Transitioning from PLG to enterprise

NEW: @Sheila Vashee (CMO of @Figma) joins GTMnow to share how she thinks about brand building across every stage. From selling brownies at age eight, to second marketing hire at Dropbox scaling to $1B+ in annualized revenue, to now leading marketing at one of the most beloved software brands in the world, Sheila has seen it all.

In this conversation, you’ll learn what brand actually means (hint: it's not your logo), how PLG companies make the leap to enterprise, why being obsessively close to your customers is a compounding advantage, and how AI is reshaping the marketing playbook without replacing the human craft that sets great brands apart.

Guest links:- Guest - LinkedIn: https://www.linkedin.com/in/sheilavashee/

- Guest company - LinkedIn: https://www.linkedin.com/company/figma/

- Guest company website: https://www.figma.com/

Host links:

- Sophie Buonassisi - LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/

- Sophie Buonassisi - X (Twitter): https://x.com/sophiebuona

- Newsletter: https://thegtmnewsletter.substack.com

Sponsors:

- HockeyStack - the AI platform that unifies GTM data to help teams convert, expand, and scale. Learn more at https://www.hockeystack.com/

- Granola - the AI notepad that turns meetings into action by capturing context, decisions, and next steps automatically. Head to https://www.granola.ai/gtmfund  and get three months free with the code GTMFUND.

Transcript available under the episode here: https://gtmnow.com/tag/podcast/

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Highlights:

00:00 – The brownie stand: why brand building started at age eight

03:55 – How Sheila defines brand: it's what people say when you're not in the room

05:08 – Joining Dropbox as the second marketing hire

06:07 – Space Race: the campaign that defined Dropbox's early strategy

06:56 – What consumer marketing taught her about driving revenue

08:29 – Measuring brand ROI through match market testing

09:15 – How Figma thinks about brand building at a macro level

11:21 – The PLG-to-enterprise equation: what Figma did early that Dropbox waited too long on

15:02 – Why building the enterprise team is both operational and optical

17:12 – How Figma ingests customer feedback at scale

18:26 – AI at Figma: enabling human creativity, not replacing it

21:13 – What the venture side taught her about staying sharp as an operator

22:33 – Why the shift from SEO to GEO is inevitable and what to do about it

23:24 – Why Reddit is back and social is a core growth lever

24:51 – The mentors that changed her trajectory

28:59 – One piece of advice: make good $h!t

For inquiries about sponsoring the podcast, email gtmnow@gtmfund.com

GTMnow is a media brand brought to you by VC firm, GTMfund: https://gtmfund.com/