Preheat the oven to 350°F (175°C) and line two large baking sheets with parchment paper or silicone mats.
In the bowl of a stand mixer fitted with the paddle attachment, cream together the softened butter, granulated sugar, and brown sugar on medium-high speed until light and fluffy, approximately 3 minutes.
Add the eggs one at a time, beating well after each addition, then stir in the vanilla extract.
In a separate medium bowl, sift together the flour, cocoa powder, baking soda, and salt to remove lumps.
Reduce mixer speed to low and gradually add the dry ingredients to the wet mixture, mixing until just combined.
Using a spatula, manually fold in the chocolate chips and chopped dried cherries until evenly distributed throughout the dough.
Using a standard cookie scoop, drop rounded tablespoons of dough onto the prepared baking sheets, spacing them at least 2 inches apart.
Bake for 10 to 12 minutes or until the edges are set but the centers still appear slightly soft.
Remove from the oven and allow the cookies to cool on the baking sheet for 5 minutes to firm up before transferring to a wire cooling rack.