Preheat oven to 350°F. Grease and flour two 9-inch round cake pans.
In a large bowl, whisk together flour, sugar, cocoa, baking powder, baking soda, and salt.
Add eggs, milk, oil, and vanilla. Beat on medium speed for 2 minutes. Stir in boiling water (batter will be thin). Pour into prepared pans.
Bake for 30-35 minutes or until a toothpick inserted in the center comes out clean. Cool for 10 minutes in the pans, then remove from pans to wire racks to cool completely.
For the strawberry buttercream, beat butter until creamy. Gradually add powdered sugar, pureed strawberries, vanilla, and heavy cream. Beat until smooth and spreadable.
For the ganache, heat the heavy cream in a small saucepan until it begins to simmer. Remove from heat and pour over chocolate chips. Let sit for 5 minutes, then stir until smooth.
To assemble, place one cake layer on a serving plate. Spread with half of the strawberry buttercream. Top with the second cake layer. Spread remaining buttercream over the top and sides of the cake.
Pour ganache over the cake, allowing it to drip down the sides. Garnish with fresh strawberries. Let set before serving.