Gregory has a Diploma in Counselling and 10 years of experience in Disability Support. After this, he worked in various call centres and sales roles until he discovered Disability Employment. He spent 8 years in this field, beginning as a Case Officer and Post Placement Support Officer, before advancing to the role of Employment Services Coordinator and ultimately serving as a Quality Assurance Coordinator. In his position as a Quality Assurance Coordinator for Disability Employment, Gregory became a subject matter expert in the field. This expertise transitioned to his work with Inclusive Employment Australia, where he was required to further develop his knowledge on the changes within the industry.