As the creator of HearWhere, I've got a bit of experience in this live music space, and I actually started building a service to connect bands with venues which I ended up scrapping.
To start off, it would be really great to show a demo to artists of what the venues would be getting from you. You've kinda explained how to use your service and what it does, but I don't know that I understand what a venue is going to get.
As a band (which I'm not) I suspect I'd like to see that.
I'm sure you know there has been a few attempts at this space, the most recent one I'm familiar with is http://www.toursavant.com/.
In my research when I was looking into this space, I found that venues were wanted to work with local booking agents. The reason (they told me) is that they aren't in the business of promoting or choosing artist, it just isn't what their good at. That is what the local booking agent does. Of course, this depends on the venue a bit.
The big challenge that I think you are going to have is building the database of venues or booking agents.
Right now as I see it, bands can add themselves to your site, but there are very few venues that they can request to be promoted too.
I think that is the next challenge for you.
As far as the current site you've got, it's easy to navigate, and add venues, so you've so far managed that process well.
Your logo is quite pixelated, so I'd get that cleaned up a bit. I don't think you have to worry too much about the design at this stage. As long as it looks cool and professional(ish), i think you're good.
Best of luck