After graduation from Wofford, Stroup accepted a position with BB&T as a relationship banker in Spartanburg. During that time, she volunteered with the Spartanburg Historical Association on the Price House Committee. She was also a member of the Spartanburg Symphony Chorus.

In 2004, Stroup moved to Annapolis, Md., and began working with Computer Science Corp. In addition to serving as a training specialist, Stroup is a certified local systems administrator for the Next Generation Desktop and has completed the requirements to become a certified classroom trainer. She joined the Vocus team in 2007 as a software trainer.

In Annapolis, Stroup is a member of Annapolis Striders running club and sings with the Annapolis Chorale and Annapolis Chorale Chamber Chorus, which performs eight classical and pops concerts each year. In 2006, the Chamber Chorus traveled to six major US cities with the Sofia Symphony Orchestra and Chorus from Bulgaria to perform Carmina Burana with Ballet Arabesk.