Montgomery is the author of two textbooks: Smartphone Video Storytelling and Mobile Journalism. His documentary films have won top prizes at film festivals in Hollywood, Moscow and Berlin. Based in Berlin, Montgomery leads mobile journalism and mobile filmmaking training courses for clients worldwide: Both online and in person. Montgomery teaches mobile journalism and design thinking courses at journalism schools like the Scripps School at Ohio University, Stockholm University, American University Cairo, and the EFJ school of journalism in France. He is the chair for the Mobile Journalism Awards and is a former editor of the Chicago Tribune and Chicago Sun-Times. He founded the Smart Film School in 2015 as an online academy offering certificate courses and campus licenses for schools. His training courses are used by reporters at CNN, WAN-IFRA, Mediacorp, BBC, Journalism Co UK, The New York Times, BILD, Russ Media, 24Sata, VRT public television, TV8, RTL, TVN, the United Nations, and Reuters.