Jack Bole, from Naples, Florida, attended Naples High School. During his time in high school, Jack was named Naples Daily News Boys Soccer Player of the Year, 3x All-Area, 3x All-Conference, Naples High School Student-Athlete Award, Naples Academic Honors, and All-State District Most Valuable Player. He also played with the Azurri Storm at the club level, winning a CASL title and the Disney Showcase in 2017, and captained his team to a Disney qualifier championship in 2018.
Jack attended UNC Greensboro, playing in 6 games. In 2022, he transferred to Florida Gulf Coast University, playing 8 games while scoring a goal. In 2024, Jack transferred to Lake Erie College, playing 9 games, starting 7, while providing 3 assists. Jack previously played for Inter City FC of the UPSL.