Preheat oven to 350°F.
Line three baking sheets with parchment paper.
In a large bowl, beat butter and cream cheese together until smooth, about 2 to 3 minutes.
Add sugar, egg, and vanilla. Beat until fluffy, about 2 to 3 minutes.
In a separate bowl, stir together flour, salt, and baking soda. Add dry ingredients to wet ingredients and beat just until well mixed, about 30 seconds.
Using a cookie scoop or measuring spoon, scoop out cookies in 1½ tablespoon size. As each cookie is scooped, use your hands to roll it into a ball then flatten it into a patty about the size of the palm of your hand (be careful not to flatten these too thin). When flattened, these should be about 2 inches in size.
Place unbaked cookies 2 inches apart on parchment covered baking sheets.
Put into the oven and bake for 9 to 12 minutes until cookies no longer look wet on top. You don’t want to overbake these. The cookies will be just slightly brown around the edges.
Remove cookies from the oven and let cool while you make the caramel.
To make the caramel, place all 40 unwrapped caramels and 2 tablespoons of heavy cream in a medium glass bowl. Place in microwave for 30 seconds then remove from microwave and stir. Then put back into the microwave for an additional 30 seconds and stir until caramels are completely melted.
Spoon about a ½ tablespoon size of caramel on the top of each cookie. Drop the caramel on the top middle of each cookie then use a spoon to slightly push the caramel towards the edges to create a larger circle of caramel (not too close to the edges though as you don’t want the caramel to drip off the sides of the cookies).
Place the tray of caramel topped cookies into the fridge to chill while you make the chocolate ganache topping.
In a medium glass bowl, heat the heavy cream in the microwave for 30 to 45 seconds just until boiling. Remove from the microwave and immediately pour the milk chocolate chips into the heavy cream. Let sit for 5 minutes before stirring.
Stir chocolate chips with heavy cream to completely melt the chocolate. Use a spoon to carefully drop about ½ tablespoon amount of melted chocolate onto the top middle of each cookie. Again, use the spoon to push the chocolate more towards the edges but not too close or it will drip over the edges.
Chill cookies in the fridge until the chocolate is completely set. Cookies can then be stored as a flat layer in a sealed food storage container or bag at room temperature or in the fridge.