Divide challah dough into 2 equal parts for 2 separate loaves. Divide each part into 3 equal pieces and roll them into long ropes using evoo to prevent sticking.
On a lightly floured surface, flatten each rope with a rolling pin. Spread pesto in an even layer over the dough leaving space near the edges. Roll up the dough onto itself until it is back in a rope.
Braid each set of 3 stuffed ropes together. Transfer to prepared baking sheet. Cover and allow to rise for 1 hour.
Preheat oven to 350°F brush challah with egg wash and bake 35-40 minutes or until the surface is golden brown.