When Scale Doesn’t Make It Easier
Sales is hard, however big your company is.
Yesterday, I went to a talk by the founder of a SaaS company worth over $10 billion. Like Superthread, they’ve built a horizontal SaaS product — one that can serve many different industries and personas. And like anyone building horizontal SaaS knows: that flexibility creates as many challenges as it does opportunities. Selling is hard. Positioning is hard. Focus is hard.
I’ve seen many founders speak — often from companies far larger — but most of the time, their advice feels detached. They share lessons polished by time, packaged into neat frameworks that sound good on stage. It’s rare that you hear something raw.
This talk was different.
Despite everything they’ve achieved — 10x growth, massive revenue, global footprint — the founder was genuinely humble. What struck me most was how familiar his current reality sounded. He’s still doing founder-led sales. He’s still personally picking up the phone, trying to close 100-seat deals. And often, it still goes nowhere. Just a few days before the talk, he’d pitched a prospect who quickly dismissed him: “We don’t need this.”
The key insight for me: the friction doesn’t really go away.
At $10B or at our size, you’re still facing the same uphill battle. The same skepticism from buyers. The same need to explain why this matters. The same rejection.
The founder’s advice was simple: you just have to keep going.
No shortcuts. No magic unlock. Just the grind — at every stage.
For me, hearing that was both grounding and motivating. It’s easy to assume that once you cross some threshold — $10M, $100M, $1B — things start to click into place and sales get easier. But in reality, it’s often just more of the same. Bigger numbers, same friction.
It was one of the most honest and refreshing conversations I’ve had in SaaS. And a useful reminder that the struggle isn’t a sign you’re doing it wrong — it’s just the nature of building something that matters.