The Enterprise Bet That Paid Off
Sheila Vashee knows what happens when PLG companies wait too long to build enterprise. At Dropbox, she watched the company scale past $1 billion in revenue as the second marketing hire. At Figma, she helped capture 95% of the Fortune 500 by doing the opposite: building an enterprise team early.
The difference? Optics and infrastructure. "Enterprise customers need to see you are invested in their success before they will bet on you," Vashee said in a recent interview. Figma built the team before they strictly needed it. That early investment signalled credibility and created the operational capacity to land and expand in large accounts.
Dropbox waited. Figma did not. The results speak for themselves.
Brand Is Every Touchpoint, Not Just Marketing
Vashee defines brand as "what people say about you when you are not in the room." That includes how support teams talk to customers, how AEs engage buyers, and what the product actually delivers. "Every person at the company is a node of brand," she said.
For sales leaders, this matters: your team is not just executing strategy, they are building or eroding brand equity with every interaction. Comp plans, quota relief, ramp periods, and how you handle deal slippage all feed into what buyers and sellers say about you when you are not in the room.
AI in Marketing: Enabler, Not Replacement
Vashee sees AI reshaping marketing strategy, particularly the shift from SEO to GEO (generative engine optimisation). Search behaviour is changing. Social platforms and third-party validation (Reddit, industry communities) are back as core growth levers because buyers trust peer recommendations over vendor content.
For B2B sales teams, this means enablement content needs to be shareable, credible, and useful outside your own channels. AI can generate drafts and analyse patterns at scale, but the human craft, understanding what resonates and why, still sets great brands apart.
The Takeaway for Sales Leaders
If you are running a PLG motion and thinking about enterprise, build the team now. If you are building a personal brand as a sales leader, remember: brand is the sum of every experience, not just what you post on LinkedIn. And if you are wondering how AI fits into your go-to-market strategy, start with where it can augment judgment, not replace it.
Vashee's one piece of advice: "Make good shit." Ship work that earns trust. The rest follows.