Townsquare’s Princeton Tiger: A Veteran Radio Sales Leader


Until two months ago, this individual served as the VP/GM of Cumulus Media’s now-former Bridgeport, Conn., stations, which are now owned by Connoisseur Media.

With the change in ownership came a shift to the President/CEO role of Coxswain Communications.

It appears a day-to-day role at a group of radio stations within a couple of hours of New York was just too tempting an offer to pass up.

Steve Chessare has joined Fairfield County, Conn.-based Townsquare Media as the Market President and Chief Revenue Officer for its group of stations headquartered in Princeton, N.J.

The three stations are Inspirational WCHR-AM 1040, FOX Sports Radio affiliate WNJE-AM 920 and heritage Top 40 WPST-FM 94.5, a Class B licensed to Trenton that has long served much of the Philadelphia DMA (even from its former home of 97.5 MHz).

Chessare reports to Townsquare SVP Rob Williams. 

“Steve Chessare is among the most talented media executives I have worked with,” said Williams. “He has led some of the biggest brands in our industry and has an extraordinary ability to build winning teams that deliver consistently strong results for our clients.” 

Chessare added, “I’ve watched closely over the past few years how Erik Hellum and Rob Williams have attracted some of the best talent in media, many of whom I have worked with before. I’m looking forward to being a part of one of the most innovative media companies in the nation.” 

Hellum is COO of Local Media for Townsquare COO. He said, “With our ‘Local First’ focus, Townsquare hires great Market Presidents for every single one of our markets, rather than splitting responsibilities across markets. Given that, I am thrilled that an incredible leader like Steve has joined the Townsquare team to run our Princeton market. One of America’s best CHRs, WPST, is in great hands!” 

Chessare has a lengthy radio resume that includes roles as a VP/GM for Greater Media in Detroit, from January 2013 to December 2016; the stations are now owned by Beasley Media Group.

From 2008-2011, he was SVP/Sales for Westwood One.

However, he may be best remembered for his role as GSM of iHeartRadio AC WLTW-FM 106.7 “Lite FM” in New York, from March 1998 to June 2008.

Chessare took that role after serving as VP/GM for CBS Radio Sales. This position saw him guide a staff of 53 people in 11 offices of national account executives, representing 63 radio stations owned by CBS and Jefferson-Pilot.

His entry into radio came in 1987 as an AE for WCBS-FM in New York.