What Slack taught me about building pricing that actually scales (and why most founders get it wrong)
I’ve been obsessing over SaaS pricing for the past five years, and I keep coming back to one story that changed how I think about the whole game.
Back in 2013, when Slack was just getting started, they had this massive problem. How do you price something when your customers are so wildly different? I mean, think about it — a tiny startup might send maybe 100 messages a day, while some Fortune 500 company is pushing 100,000 messages across thousands of employees.
Most companies would panic and just pick some random middle ground. But Slack? They got creative.
They built their pricing around multiple things at once:
Pay per user who’s actually active
Different feature sets for different needs
Storage that grows with each plan
More integrations as you pay more
The result? They somehow managed to make money from broke startups AND massive enterprises paying hundreds of thousands yearly. When they went public, they were worth $26 billion.
That’s when it clicked for me — your pricing isn’t just about making money today. It’s about building a machine that grows with your customers.
Look, I get it. When you’re starting out, pricing feels impossible. You’ve got this product that took months to build, and you have no idea what people will actually pay for it.
So what do most founders do? They pick one price. Usually way too low because they’re terrified of scaring people away.
I’ve watched so many smart founders make this mistake, and it always leads to the same three problems:
You’re basically giving away money Here’s what I see all the time: A small marketing agency pays $50/month for an email tool that manages 500 subscribers. Meanwhile, some enterprise with 500,000 subscribers pays the same $50. That’s insane when you think about it.
Nobody takes you seriously This one really hurts. I’ve seen founders lose deals worth six figures because their pricing was too cheap. Enterprise buyers literally thought the product wasn’t good enough because it cost too little. It’s backwards, but it’s real.
You hit a wall With flat pricing, the only way to grow is finding new customers. You’re ignoring all the existing customers who’d happily pay more for extra value. It’s like leaving money on the table every single month.
The companies that really nail this treat pricing like Mercedes treats cars. They don’t just sell one sedan at one price. They’ve got the C-Class for young professionals, the S-Class for executives, and the AMG line for people who want the absolute best.
Your software should work the same way. You need different options for different customers, and paths for them to spend more as they grow.