In a medium saucepan over medium heat, heat the heavy whipping cream until it bubbles around the edges. Pout the hot cream over the chocolate and let sit for 2 minutes.
Using a clean, dry silicone spatula, stir to combine until all of the mixture is smooth and glossy. Let the ganache cool about 15 minutes.
Prepare strawberries:
Cut the tops off the dry strawberries and gently cut out the center of the berry using a sharp knife or small melon baller, being very careful not to pierce the side or bottom of the berry. Set aside until ready to fill with cooled ganache.
Once the ganache is cooled, transfer to a quart sized zip top bag. Cut off a small portion of one corner. Fill each berry with ganache so just a bit is peeking from top. Place on wax paper lined baking sheet and chill for at least 15 minutes.
Prepare dipping chocolate:
In a medium saucepan over medium heat add remaining 1/2 cup chocolate chips and shortening. Once chips begin to melt, stir until smooth.
Remove from heat and transfer chocolate to a small ramekin or other bowl for dipping. Dip cool strawberries and return to wax paper lined baking sheet. Quickly sprinkle with jimmies or sprinkles. Return to refrigerator to set. Once set they are ready to serve.