Holy crap this is a huge topic!
I'm working on a book on Founder Sales right now, but this is just a massive, massive, massive topic.
From a hiring perspective, you should make you're hiring intelligent, figure shit out (street smart), grinders. Do not just hire "sales bros".
Then you should entirely systematize a solid onboarding that covers 100% business acumen topics (e.g., for Bright Blue, hotel concierge business, how shopping maps currently work, etc.), so your team can speak, script the hell out of it, and then cover in your onboarding all of your CRM, email, calendar, lead gen process.
We dedicated an entire first work with a full blown curriculum all lined out, along with what we called "pair programming" where new hires sit alongside existing staff to watch what's going on, and intense mock calls and script training. The later practice builds on the prior education materials.
It really is contingent on how systematized your sales process is more broadly.
I wish I had a hyperlink to just share with you, but I don't yet.
There are some posts on my blog about these early stage sales topics here: http://kazanjy.svbtle.com/
Wish I had more for you. Your startups sounds cool. Two sided market where you lock up the demand side via concierge-guided install, and then sell placement to local businesses. Much more compelling than Yelp's offerings ; )