Meet The Coaches
Stephenson Ryan
Head Coach, DS Raiders Football
The 2024 season will be Coach Ryan’s 8th as Head Coach with the Raiders. His first year was the record setting 9-2 season in 2004. Following that season, Coach Ryan resigned to spend time with his growing family. In 2017, Coach Ryan returned to the Raiders and has been developing the program ever since. Coach Ryan has been coaching football for 28 years in several programs including Dover Sherborn, Medfield, and St. Sebastians. Coach Ryan graduated from Natick High School and then Phillips Andover Academy in 1988. He played 4 years of baseball at Babson College and graduated in 1992. Coach Ryan has his team work hard in the weight-room, the classroom, and on the field.
Bobby Conrad
Defensive Coordinator, DS Raiders Football
This is Bobby’s fifth year with the Raiders. Bobby is the team’s defensive coordinator. He brings an attitude of toughness and aggressiveness. Bobby is a successful entrepreneur and owner of the Conrad’s Restaurants. Bobby graduated from Malden High School, where he played Football and Baseball. Bobby graduated from Nichols College in 1990 where he played football. Bobby has coached for over 25 years.
Eric Lochiatto
Head Offensive Line Coach, DS Raiders Football
This is Eric’s third year with the Raiders. Eric coaches the head offensive line coach and assists with defensive tackles. He is a teacher at Dover Sherborn High School. Eric graduated from Newton North High School, where he played Football, Wrestling, and Baseball. Eric has the versatility to coach any position, but Coach Ryan believes the offensive line coach is the most vital to a team’s success. Eric graduated from Curry College in 2007 where he played baseball. Eric has coached for 12 years at Dover Sherborn, Watertown and Newton North.
Rob Mosher
Head Wide Receiver & Defensive Backs Coach, DS Raiders Football
This is Rob’s fourth year with the Raiders. Rob is the head wide receiver and defensive backs coach. He is a 2015 graduate of Dover Sherborn High School where he was a football and track star. Rob graduated from Stonehill College in 2019 where he played track and field. Rob is also the team’s head junior varsity coach. Rob has also spearheaded and become the head coach of the middle school team for Dover Sherborn.
Alex Olmsted
Linebacker & Wide Receiver Coach, DS Raiders Football
This is Alex’s second year with the Raiders. Alex coaches the linebackers and wide receivers. He is a teacher at Dover Sherborn High School. A 2018 graduate of Millis High School, where he played Football, Basketball, and Baseball, Coach Ryan is thrilled to steal Alex from the Mohawks. Alex graduated from Assumption University in 2022 where he played club basketball.
Jerome Penn
Running & Defensive Backs Coach, DS Raiders Football
This is Jerome’s second year with the Raiders. Jerome coaches the running backs and defensive backs for the Raiders. Jerome is a versatile and bright young coach who can coach any position. A 2014 graduate of English High School, where he played Football, Basketball, and was also a boxer. Jerome graduated from UMass Boston in 2019 where he played football and basketball.
Mike Tosone
Head Defensive Line Coach, DS Raiders Football
This is Mike’s fifth year with the Raiders. Mike is the head defensive line coach and assists with offensive linemen. He is a teacher at Braintree High School, the school from which he graduated in 1981. Mike was a football and track star in high school. Mike graduated from Stonehill College in 1985 where he was an All-American nose-guard. Mike has coached football for over 35 years. His wealth of knowledge about the game is only surpassed by his energy and positivity.