Raymond graduated from Hamilton College in 2007 with a degree in Government and minor in Religious Studies. After studying abroad in Germany upon graduation, he joined the faculty at Berkshire School, teaching History, working in the Kenefick Learning Center and coaching football, baseball and basketball. From there, Ray spent the next 7 years coaching football at the college level at Trinity College and Rhodes College. Prior to joining the faculty at Deerfield, Ray worked for NCSA (Next College Student Athlete) consulting and guiding high school football players in their college recruiting process.