Penelope is the acting head of the Pom squad at Middleton High School, as well as an acclaimed thespian for the Middleton Theatre Troupe. As the victor of Middleton's most recent Pep Rally, she currently holds the Middleton Pep Trophy in her possession.
For many years Penelope was known as an "ambitious under-achiever", due to her constant attempts at elevating the social esteem of underrepresented student groups. Despite her potential to serve as a lower-tier Cheerleader at Middleton High School, she instead joined the Pom squad and dedicated herself to the cause of instigating a "Pom revolution", which would turn the disrespected, amateurish group into a championship team.
Penelope's dream came true at the 85th Annual Pep Rally when the Pom squad she led won the Dance Off in a controversial victory. After this victory Penelope's social status was significantly elevated, allowing her to pursue other ventures.
Penelope branched out from the Poms and began dabbling in the theatrical arts. Her performances were well-received by the Middleton Theatre Troupe, and she eventually won herself a leading role in Middleton's production of "The Cheerleader Trials".
Penelope's allegiance to the Pom squad is partially inspired by a long family tradition of Pom-ing. Most notably, Penelope's grandmother was the head of the Middleton Pom Squad during the early 20th century, and was said to have nearly won the Pom's first ever dance off; her efforts were squandered, however, when she was supposedly sabotaged by a laser-pointer.