Ads management intergration

I am using the geodirectory. What we would like to implement is the ability for the business directory owner to also include an ad that will automatically get inserted in an ad management product we want to implement into the wordpress site. We did not decide on which ad management product to use yet. We want to charge one fee for the listing and if the business owner chooses or checks off a box to also have an ad running throughout the site the have to pay for a higher listing. That ad image would be uploaded to the listing and also we want it to be available in the ad management product. Is this something that you have an ad on for or a way to implement?