Originally Answered: Should I find another job?
I feel for you.
My first job out of college was selling display space for a local newspaper, and I didn't like it much. I hated making cold calls.
As you have no doubt discovered, advertising sales is totally unlike retail sales. Sure, it helps to be personable and articulate, but you are selling something intangible. A lot of customers have a problem dealing with that.
If you are willing to stick it out, here are some things you might consider doing.
Find out where your prospects are currently advertising. Study their ads; study your competition. If you feel as though the prospect would be better off with your station or advertising medium, be prepared to discuss why.
See if you can get a hold of a rate card from your competitors. The more you know about their rate strucuture and services, the better. For instance, you may discover that while your competition offers lower rates, it requires that the client pays for production. How does this compare with how your company does business?
If you are able to land an appointment, try to go in with a sample ad. Show your customer how it might look in your publication, or be able to tell them the time slot you recommend it be broadcast. The more "tangible" you can make their ad, the better your chance of selling them.
When I sold ads, I made it a practice to write and design the ad before I met with the client. This accomplished two things: it gave the client an idea of how their ad would look in my publication and it underscored my enthusiasm to work with them.
Finally, keep in mind that your prospects receive dozens of calls from ad reps every week. So you need to be able to tell not only your own story, but you need to be able to explain why you are better than alternative media: are you more cost efficient? Is your media more targeted to THEIR customers? Do you offer free advertising services that they might otherwise have to pay for? Are you able to offer discounted rates on a contract basis? Do you reach a wider audience?
The better you understand your prospective clients AND their customers, the more successful you will become.
It sounds like you are already doing a lot of research, and I've no doubt that you have the tenacity to want to make this opportunity work out. I hope it does - if that is where your heart is at.
At any rate, good luck with your baby.