He began his career as a graphics journalist at the Fort Lauderdale Sun-Sentinel in 1990 after graduating from Eastern Illinois University with a degree in journalism.

In 2018, Routledge Press (New York and London) published Montgomery's second book "Smartphone Video Storytelling" as a hybrid textbook that includes a rich library of e-learning materials.

[6] In 2011, he developed the mobile journalism training, technology and workflows used by hundreds of Radio Free Europe (RFE/RL) reporters and correspondents in 23 countries.

[8] He is a distinguished visiting professor at the EFJ School of New Journalism in Paris and at American University, Cairo where he leads Mobile Reporting and Story Lab workshops to promote entrepreneurial and video storytelling.

[9] He designed the IREX Multimedia Education Center, a USAID-funded broadcast training facility in Tbilisi, Georgia built entirely around mobile journalism.

[10] Montgomery is the founder of the Smart Film School an online academy that produced diploma courses and certified training in mobile journalism and documentary filmmaking.