Chebot began his professional career as a producer for WBZ-TV Boston's Evening Magazine. In 1988, Chebot founded Parallax Productions, Inc., a video, multimedia and film production company that works with a diverse client base including television networks, media companies, public relations and advertising agencies, corporations, and foundations. Parallax Productions is headquartered in Boston, Massachusetts, with crews all over the U.S. and many countries around the world. Parallax produces broadcast programming, documentaries, commercials, PSAs, and web content.
In the late 90s, he was the creator, executive producer and director of the nationally syndicated television series, The Wild Wild Web. The series ran for three seasons and was considered the television guide to the Internet. Distributed by CBS/King World, The Wild Wild Web series aired in 148 U.S. markets.
In 2006, Chebot produced, wrote, and directed Song for New Orleans. Broadcast nationally and distributed internationally by Hearst Television, the feature-length film chronicles the rebirth of the New Orleans music scene immediately after the devastation of Hurricane Katrina, and won two bronze Telly Awards.
From 2011–2015, Chebot directed and executive produced Outermost Radio, a feature-length documentary film about a community on the tip of Cape Cod and their non-profit community radio station WOMR. Outermost Radio was selected by the Provincetown International Film Festival where Chebot won The John Schlesinger Award and was also selected by the Kansas International Film Festival, the St. Louis International Film Festival, and the Hamptons Take 2 Documentary Film Festival in 2015. In 2016, Outermost Radio continued its festival tour at Idyllwild International Festival of Cinema in Idyllwild, California, where Chebot was awarded Best Director, and at the International Filmmaker Festival of World Cinema in London, and at the International Filmmaker Festival in Nice, France. In April 2016, Outermost Radio won the prestigious Remi Award at the WorldFest Houston International Film Festival.
In July 2016, Chebot was the Executive Producer and Director for OZY Fusion Fest's hour-long broadcast special. The festival took place in Central Park, New York City, and featured music from will.i.am and Wyclef Jean, comedy from Abbi Jacobson and Ilana Glazer, and conversations with Malcolm Gladwell, Cory Booker, and Karl Rove. The festival was a partnership between OZY Media and Fusion, airing on Fusion Networks in August.