The Customer Onboarding Mistakes That Kill Your Growth
Today’s advice post is by Dan Lesley, Founder of Homestar. Dan has over 20 years building, growing, and selling SaaS tech startups.
Back when I started Homestar, I was that typical founder wearing too many hats and barely keeping up. Onboarding customers properly? Yeah, that kept me up at night. Nothing kills momentum faster than users giving up because they can’t figure out your product. I’ve got the battle scars to prove it.
We really messed up at first. Rushed the launch, skimped on proper onboarding because we were impatient. Thought we could just hand everyone the same generic tutorial and call it a day. Real estate agents would laugh at that now - each one had such different tech comfort levels and needs. Some could barely attach files to emails, others were running complex marketing automation.
Then there was our brilliant idea to dump every single feature on new users immediately. Because more is better, right? Wrong. Poor users looked like deer in headlights, completely overwhelmed by options they didn’t need yet. Made about as much sense as teaching someone parallel parking before they know how to start the car.
- Personalize the onboarding experience for different user levels
- Roll out features gradually, focusing on immediate value
- Listen to feedback and iterate
We were terrible listeners in the beginning. Users would give us gold - telling us what wasn’t working - but we were too busy “building features” to really hear them. People signed up excited to use the product, then felt abandoned when we ghosted them after getting their credit card info.
Regular check-ins changed everything. Simple stuff like messaging users “Noticed you closed those deals using our automation feature - killing it.” Actually showing we paid attention made a huge difference. Turns out people appreciate when you notice their success.
Support was a joke early on. Just me and my cofounder trying to handle everything ourselves. Users would wait days for basic help. Pretty awful feeling when you’re stuck on something simple but can’t reach anyone. Adding live chat and boosting our support team changed the game completely.
The automation obsession hit us too. Started programming everything to run automatically until the whole experience felt robotic. Learned that lesson at my previous startup - you can’t automate away the human connection. Sometimes a quick “ Dan from Homestar here - how’s it going?” works better than any automated sequence.
We also totally whiffed on showing actual results. Expected users to just trust that our software was helping without proving it. Once we started showing real numbers - time saved, deals closed, productivity gains - everything clicked. People could finally see what they were getting for their money.
Building Homestar has been messy. Onboarding especially. But each failed attempt taught me something valuable. Maybe sharing these mistakes helps someone else avoid them. Still learning every day.