Gerald started his career as a television reporter across New Jersey, New York, and Pennsylvania. He spent most of his time as a political reporter, covering the New Jersey State House, New York City Hall, presidential candidates, and political conventions. He worked on-air for four TV stations and has also appeared on CNN and the Weather Channel. Gerald eventually became a producer for several stations and moved into news management as an Executive Producer for a 24-hour cable news network.

Later, Gerald worked in for a global technology company where he managed corporate communications and marketing campaigns. In 2017, Gerald launched D’Ambra Media where he has since worked with global brands, placed national media, and counseled executives on crisis communications and media relations.

Gerald is also the founder of On Air Media, a company focused on building streaming TV apps such as NJ on Air and ChristmasFlix. On Air Media also produces original programming and works with TV networks and production companies to develop new shows.