Learnings from #Saasiest, day one, part 2 Companies bought a SaaS for every problem. Don't make the same mistake with AI. This hit hard. We're repeating the SaaS bloat problem with AI tools. Different wrapper, same chaos. Your teams are drowning in tools they don't need, can't integrate, and won't use six months from now. The growth chaos nobody talks about At 30 people, you have no silos. Everyone talks to everyone. At 100 people, you get org chaos. Departments form. Communication breaks down. Left hand doesn't know what the right hand is doing. This is where most B2B companies start bleeding revenue. Not because the product fails. Because the org structure can't support the growth. Leadership swaps kill momentum Here's the pattern: Company hits a rough patch. Board blames leadership. New leaders come in. They blame the previous leaders for everything. Then they leave. "We hired amazing leaders... just at the wrong time." This cycle destroys trust. Your team stops believing anyone knows what they're doing. If you're swapping leaders every 18 months, the problem isn't the leaders. It's that you don't know what you need from them. PLG vs sales led: pick a side You can't serve two masters. Enterprise first means sales led. Long cycles. Custom deals. White glove service. Product led means self-serve. Fast onboarding. Low touch. Users become evangelists. Companies try to do both and end up mediocre at everything. The product team builds for self-serve users. The sales team promises custom features to close enterprise deals. Now you're supporting two different products with one team. Pick one. Get good at it. Then maybe you can add the other motion later. Most companies should start product led and move upmarket. But if you're selling to enterprise from day one, own that. Build for their buying process, not for the motion you wish you had. What's killing your GTM motion Three things break go-to-market at scale: First, you have no clear ICP. You're chasing every deal that comes in because you need the revenue. Your sales team doesn't know who to target. Your marketing doesn't know who to speak to. Second, your pricing doesn't match your product. You built for SMB but you're trying to sell to enterprise. Or you built for enterprise but your pricing scares away the companies who actually want to buy. Third, your teams aren't aligned on the same goal. Product wants usage. Sales wants revenue. Marketing wants leads. Nobody's talking to each other. Fix the org structure first You can't scale revenue if your org is broken. At 30 people, put everyone in the same room once a week. At 100 people, create clear swim lanes but force cross-functional meetings. At 500 people, you need executive alignment or the whole thing falls apart. Most founders skip straight to hiring and wonder why nothing works. The people aren't the problem. The structure is.