FEATURED MOVER | Ashley Raymond, What’s Up? Media

Ashley Raymond, the chief operating officer of Annapolis-based publishing company What’s Up? Media, was named one of the 2019 Top Women in Media by Folio, a national magazine and digital publishing association in New York. The Crownsville resident was recognized in the Up and Comers category, a designation given to women who are making a mark at early stages of their career.

Raymond started at What’s Up? Media as an office administration intern during her senior year at South River High School 17 years ago. After graduating in 2003, she took a full-time position as a production assistant. A few years later, she became the circulation, events, and production manager. In 2012, the company promoted Raymond to operations publisher. This role demanded her insight regarding overall company operations and the development of marketing concepts to enhance the company’s branding, outreach, and portfolio of advertising opportunities. She was then named COO in 2016.

Outside of work, Raymond is a fierce community advocate and volunteer. As vice president of the Herald Harbor Citizens Association, she has organized several fundraisers to support the construction of a new park and pavilion. She is also the founder of Friends of Herald Harbor, a community organization that educates and empowers youth. In addition, she coaches Arden Recreation T-ball, volunteers South Shore Elementary and will become a Master Watershed Steward and leader of Girl Scout Troop 10246 later this year.

As a result of her commitment to her company, co-workers, and community, Raymond received What’s Up? Media’s annual MVP Award in 2009 and 2017.

Ashley Raymond, chief operating officer of What’s Up? Media

Ashley Raymond, chief operating officer of What’s Up? Media


Resides in:

Herald Harbor which is in Crownsville, Anne Arundel County


Anne Arundel Community College

What pushed you toward your interest in sales and marketing? 

I took a Marketing Track in High School, after winning an award for our school DECA team – my teacher recommended me for the position when What’s Up? called the following week looking for a new office assistant.

If you had not chosen media as a profession, what profession would you choose and why?

That’s a tough one. I probably would have chosen something related to the Bay – maybe within a non-profit, Maryland DNR or even a waterman’s workboat.

Favorite vacation:

I have been all about experiences, this winter I went skiing for the first time in Deep Creek.  I will never do that again. Another recent vacation was with my 8-year-old daughter, the past two years she would complain about getting on a plane because she was scared.  Instead of letting her continue this fear, I took her across country to San Diego to visit a friend of mine. If I were to ever move to another area, San Diego would be for me.

When I want to relax, I …:

Fish or read a book alone at sunset in Valentine Creek on the Severn River.

Favorite music:

When I don’t have “kids bop” playing for my daughter on XM – my favorite station is 90s on 9.

Favorite quotation:

“Success isn’t just about what you accomplish in your life, it’s about what you inspire others to do”





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