After starting serious private study with Corey, Jesse began playing with the Portland Youth Jazz Orchestra under the direction of the legendary Ben and Michelle Medler. He still plays in the top advanced jazz combo nearly 10 years later.

In Jesse's high school years, he began playing his first jazz gigs around the Portland Metro Area. He began playing other shows with his progressive rock trio Action Roadster, his duet project JDUO, and local New Orleans style brass band Couch Brass. He also worked with Chris Brown and his All-Star Metropolitan Youth Symphony Jazz Band, and the Portland Jazz Composer's Ensemble, Towards the end of high school, Jesse became the regular drummer for The Chris Baum Project and The Dan Kaufman Band. Out of high school, he joined The Infatuation and cureelenly has several projects in the works.

Outside of Jesse's gigs, he enjoys composing for his solo project Sleep OK, and is attending Clackamas Community College to become a recording and sound engineer. He also holds an internship at The Hallowed Halls, where he's worked with famous producers such as Billy Anderson.