Conrad began his career as count of Assisi, which was given him after its 1174 conquest by Christian of Mainz. Frederick Barbarossa, the emperor, invested Conrad as count and granted him the Rocca as his seat of power. During his countship, Saint Francis was born at Assisi.
In 1183, Frederick appointed him duke of Spoleto. In 1190, he was chased from Spoleto by the ascendant Guelph powers, but he regained his duchy in 1195. He briefly sheltered the young Frederick II at the Rocca and acted as the vicar of the Kingdom of Sicily, but in 1198 he was ordered to render Spoleto to the pope and during his absence, Assisi rebelled and declared a commune.