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Who we sat down with
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.
Discussed in this episode
Why brand is the sum total of every experience (not just pretty visuals)
What being the second marketing hire at Dropbox through $1B+ in revenue taught her about early-stage strategy
How Dropbox’s Space Race campaign blended marketing into company strategy
The PLG-to-enterprise equation: what Figma did early that Dropbox waited too long on
Why building the enterprise team early is both an operational and an optical investment
How Figma ingests customer feedback at scale using quantitative tools + live user research
The role of AI at Figma: enabling human creativity, not replacing it
What the shift from SEO to GEO means for marketing teams
Why social and third-party validation are back as core growth levers
How consumer marketing experience shaped her approach to measuring brand ROI
The mentors that shaped her career and the question that changed her trajectory
Her one piece of advice for anyone building a brand right now: “make good $h!t”
Episode 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
Key Takeaways
1. Brand is the sum total of every experience (not a logo or a campaign).
It’s what people say about you when you’re not in the room. It’s how your support team talks to customers, how your salespeople engage buyers, and the experience your product delivers. Every person at the company is a node of brand.
2. The PLG-to-enterprise leap requires an intentional, early investment.
Figma built an enterprise team far earlier than most PLG companies do and it paid off. It’s the reason 95% of the Fortune 500 now uses Figma. But optics matter more than you’d think: enterprise customers need to see you’re invested in their success before they’ll bet on you.
3. Customer obsession is the new operating model.
Figma’s founders flew to Nigeria to meet early users. Their product support team feeds insights directly back to product. They have 200+ Friends of Figma chapters running worldwide. And their user research sessions are open for anyone at the company to watch live. That closeness to the customer is embedded in the Figma DNA, and it shows up in the product.
4. Measuring brand impact requires creativity.
Sheila ran match market tests at a previous company by fully treating one city with TV, billboards, and brand spend while keeping comparable cities at steady state. The ROI was clear. For brand skeptics who say you can’t quantify it: design the experiment, isolate the variable, and let the data speak.
5. AI enables human creativity. Human taste will always win.
Figma sees AI as a massive enabler. Tools like Figma Make let you generate 20 prototypes in 20 different directions. But the judgment on which path to take, the craft that brings it to life, that’s still human. Sheila’s push to the marketing community: don’t fall into the AI slop trap. MAKE GOOD $h!t!
Follow Sheila Vashee
LinkedIn: https://www.linkedin.com/in/sheilavashee
Figma’s LinkedIn: https://www.linkedin.com/company/figma
Figma website: https://www.figma.com/
Follow Sophie Buonassisi (Host)
X (Twitter): https://x.com/sophiebuona
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