Jenna Orlando is from New Jersey where she attended Bloomfield High School and played softball and volleyball.
She then went on to play Division I collegiate softball for Lafayette College from 2013-2017. Jenna was a four-year starter for the Leopards - primarily playing shortstop and outfield, also seeing time at second base. She served as Captain in her senior year and was named to the Patriot League Academic Honor Roll from 2014-2017. Jenna received the Lafayette Softball's Coach's Award in 2015 and Leadership Award in 2017.
After graduating with a Bachelor of Arts degree in Psychology, she joined The Headfirst Companies as a Leadership Fellow, spending a summer working at the New York Yankees Summer Baseball Camps, before quickly being promoted to the role of Associate of Baseball and Softball Operations. Within this role, she works within both their Professional Sports Camp and Honor Roll Camp divisions.