In one of its largest early deals, Trailhead Media acquired InSite MediaCom’s billboard operations in October 2020, adding 1,271 advertising faces across Georgia and South Carolina markets near the Georgia border.
A Decade in the Making
InSite MediaCom’s portfolio was built over more than ten years through acquisitions and organic development, making it one of the largest independent outdoor operators in the Southeast by face count at the time of the sale.
Max Drachman of Kalil & Co., who represented the transaction, said InSite’s scale was part of what made the deal stand out: “It is difficult to replicate that number of faces anywhere in the U.S.”
The acquisition became a cornerstone of Trailhead Media’s Georgia and South Carolina inventory, supporting the network the company continues to build across the region today.
Source: Billboard Insider

