Rob grew up in South Hero until the age of 12, when the Coles moved to South Burlington before attending SBHS. Rob joined his first Far Post travel team in 1999 when he was 8 years old. He played for Far Post for 10 years, from 1999 to 2009, with State Cup victories in 2001 and 2009. He was one of two Far Post players, along with Adam Batista, to be selected to the ODP Region 1 Pool in 2007 as U16's. In fall 2008, in his Senior High School Season, Rob earned All-American and Gatorade Player of the Year honors for the state of Vermont, and was the MVP of Vermont's Twin State victory over New Hampshire in the summer of 2009.
Rob started coaching at Far Post camps when he was 17 and became an assistant coach for his first travel team as a senior in high school. Rob returned to coach travel teams for Far Post in 2013 after 4 years of varsity soccer at Middlebury College. Since graduating, he coached the UVM Men's Club team for one season, then the South Burlington High School Varsity Girls' program for two seasons. Rob became the Head Coach of the Champlain Valley Union Varsity Boys' program in early 2017.