On September 1, 2011, in his debut as a high school freshman, Sills earned ESPN HS East Region Player of the Week for games of August 25–27 for 17 for 21, 221 yards and four touchdowns in a 54–18 defeat of 2010 Ohio High School Athletic Association Division V state champion Ursuline.[20] For his freshman 2011 season, he totalled 2,340 yards and 28 touchdowns in what was his second year as a varsity quarterback. He was named a MaxPreps.com U.S. Air Force Second Team Freshman All-American.[21][22] Following a freshman season, where father and coach David Sills IV contributed to financing an entirely out-of-state schedule including air travel games to California,[23] Red Lion Christian Academy took actions to downsize its athletic program.[24]
On July 1, 2012, he led his team to the National 7-on-7 Championships.[25] As a sophomore, Sills became the quarterback for Eastern Christian Academy (ECA) of Elkton, Maryland. The move was controversial because the school is a newly formed online educational institution. All boys that are enrolled are on the 46-man football team established by David Sills IV to showcase their talents to college scouts.[26][27] Eastern Christian Academy was only able to play in 3 games in 2012 due to the school's failure to gain accreditation from the state.[28][29]