I am a connected connector, a problem solver, creative director, and software developer who likes creating effective marketing strategies that help businesses grow.
Obviously checking their example work is important, but in addition I like to ask them how they built the app they're showing as an example. If they can answer confidently and clearly then they probably did build it.
Great developers are concise and logical. Bad developers are disorganized and illogical.
You can't really tell a good developer from Kait talking to them though. I would recommend breaking the project down into 5-10 "sprints" where they have something to show you at each step. Ask them to set the time frame for each sprint and if they meet each sprint deadline on time and have the majority of the work to show at each milestone point then you're good to go.
Test whatever you can each step of the way so that you can get what you need functionally.
When I'm asked to sit on a board I ask myself:
1. Will this entertain me and will I have fun?
2. Can I contribute something of value?
3. Will these people listen to my advice if they aren't paying for it?
4. Will I learn something or become connected with other board members who matter to me?
All of these factors play a big part for me. They're all valuable components. So if too many don't add up in my favor I pass on the board.
Before investing a single dollar in advertising - invest wisely in outstanding copywriting. Then you should test your advertising on Facebook. That's one of the simplest and most cost effective places to test how to get the best return on your marketing investment.
Then grow from there: http://tekk3.com/are-you-buying-a-marketing-machine-gun-or-a-bomb/
That's something that sounds like a good fit for a custom solution. It wouldn't have to be terribly expensive, probably between $5000-10,000.
I don't know of any software that's already out there that does that. It could be a great business opportunity though if he has the connections to the training centers, because he could be a connection point for people looking for training. Either consumers or business would pay for the service.