DocSend

So heres a fun story. When we started using DocSend back in 2023, we got their startup plan. $15 a month per user. Three of us on the team needed it. $45 total. Totally reasonable. Fast forward 14 months. The startup discount expires. No warning email, no heads up, nothing. I just see a charge on our card for $150. I had to dig through the billing page to figure out what happened. Turns out the "standard" price was $50/user/month. Times three users. $150. And look, i understand companies need to make money. But a 10x price jump with zero notice? Thats rough. Especially when you've built your entire document workflow around the tool. Per-user pricing is a trap for growing teams The thing about per-user pricing that nobody tells you upfront: it gets worse exactly when your team is growing, which is exactly when money is tightest. We had three people initially. Then we hired two more salespeople. Suddenly were looking at $250/month just for document sharing. For context, our entire Slack