Joined an AI Startup with Ex-ShipStation Team - Need Tips on Finding Early Users

Hey Reddit,

My name’s Welcome (Yes, that’s really my name), and I’ve been in tech for most of my career, mostly at bigger companies with established brands and resources. But recently, I decided to join a small startup called BotDojo.

It’s my first time being part of a small team, and it’s been a pretty eye-opening experience so far. But, like with anything new, I’ve hit a few bumps along the way, and I’m hoping you all might have some advice.

A little backstory: BotDojo was started by some of the engineers who used to work together at ShipStation. After ShipStation sold, they spent some time experimenting with AI but kept running into the same problems—having to patch together tools, getting inconsistent results, handling data ingestion, and struggling to track performance. So, they decided to build a platform to help developers build, test, and deploy AI solutions.

Since I came on board, my focus has been on finding early users, and it’s been a mixed bag of wins and frustrations. We’ve got a solid group of people using the free version (which is great), but only a few have upgraded to the paid plan so far (ranging from startups to large enterprises).

The cool thing is that those who have become paying customers absolutely love the product. It’s just been hard getting more people to that point.

We’ve tried a bunch of things: Attending industry events, doing cold email outreach, running social ads (the usual stuff). And while we’ve seen some interest, we’re running into a few challenges:  

• Learning curve: The software is really powerful, but it takes a week or two for users to really see what it can do. Without a dedicated sales team to walk them through it, it’s been tough getting people to stick around long enough to see the value.
• Standing out is hard: The AI space is super crowded right now. I think a lot of people see “AI tool” and assume it’s just like everything else out there (even though BotDojo has some awesome features that really set it apart). 
• Sign-ups, but limited engagement: We’re on a freemium model to make it easy for people to try it out, but that also means we get a lot of bots and people who sign up but don’t really dive in.

So, I thought I’d reach out here and see if anyone has been through this early stage before. How did you manage to break through and find those first paying users who really saw the value in what you were building? 

Are there any strategies, communities, or tactics that worked particularly well for you? And if you had to do it all over again, what would you focus on?

I figure I’m not the only one trying to navigate these waters, so I’m hoping this can be a helpful thread for others too. Thanks so much for reading, and I’d be super grateful for any advice or insights you can share! 🙏