Who’s Succeeding Jimmy deCastro In Chicago?

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Entercom, via an internal memo distributed Wednesday by COO Weezie Kramer, has confirmed that it has selected a new Regional President for its Milwaukee and Madison, Wisc., stations who will also serve as the full-time Market Manager for its Chicago stations.


It’s the woman who’s been running Gamut, an arm of Cox Media Group, since 2016.

Succeeding Jimmy deCastro in the dual Wisconsin/Illinois leadership role is Rachel Williamson. 

With experience in local and national radio and in digital, Williamson built “an innovative first to market OTT company with premium advertising offerings for local broadcast and launched proprietary technology and data attribution partnerships to better operationalize business efficiencies,” Kramer said. “I am thrilled to welcome Rachel to the company, and I think her energy and multiplatform experience will help take us to the next level.”

Williamson is expected to join Entercom “in 2020.”

As RBR+TVBR reported Nov. 15, come mid-December, De Castro will focus entirely on TCF and After The Whistle. That’s the sports marketing and talent representation firm linked to The Content Factory.

Williamson joined Cox Media Group as Director of Digital Revenue Development in February 2015. Before that, she was at Cumulus Media, where she held the title of Midwest Director of National Sales.

She’s also been a Senior Account Executive for the Midwest at Nielsen, and in her first stint with Cox held sales roles in New York and in Louisville.

Williamson began her career as an account manager, in 2004, for Forever Broadcasting in Bowling Green, Ky.

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