In 2013, Mr. Cross began his career in education teaching ESE(Exceptional Student Education) and mathematics at Cocoa High School. In 2019, Mr. Cross was Cocoa High Schools "Teacher of The Year". From 2017 to 2019, Mr. Cross's ESE middle school math classes had one of the highest average increases on the FSA mathematics examination compared to all other FSA exams throughout the county.

In 2019, he had 96% of his students experience gains with an average increase of 21 points for each student. Because of Mr. Cross's success in the ESE classroom, he firmly believes that all students are capable of success, no matter their educational background. Mr. Cross also coached wrestling for nine year(four years at Cocoa Beach High School and five years at Cocoa High School).

In 2019, Mr. Cross stepped away from coaching to pursue a career in educational leadership. He was a part time night teacher at Brevard Adult Education for two years starting in 2019. In June of 2021, Mr. Cross left Cocoa High School after 8 years to became the new administrator at the Central Brevard Adult and Community Education Center in Cocoa.