Preheat the oven to 350°F. In the bowl of a stand mixer, beat the butter and sugar together just until combined, scraping down the sides as necessary. Add the vanilla and beat to combine.
In a medium bowl, sift together the flour and salt, and then add them to the butter mixture with the mixer on slow. Continue mixing on slow just until the dough starts to come together. Dust your work surface with flour and scoop out the dough onto it. Shape it into a thick rectangle and wrap in plastic wrap, then chill it in the fridge for ~30 minutes.
When ready to bake, roll the dough out until it's 1/2" thick. Cut 2 1/4" x 3" rectangles out of the dough, reshaping the excess and rerolling to get more cookies. Place the cookies onto a baking sheet lined with parchment paper, leaving room for them to spread. Sprinkle with a pinch of sugar, and bake for 20-25 minutes, just until the edges begin to brown. Remove from the oven and allow them to cool to room temp.
While they're cooling, melt 6-7 oz of chocolate in a heat-proof bowl. I recommend microwaving for 30 second increments and stirring in between until the chocolate is melted. Once the cookies are cool, carefully dip one side into the chocolate and let the excess drip back into the bowl before inverting the cookie onto a wire rack to allow the chocolate to solidify. Once the chocolate is solidified, you can flip them back over and decorate the cookies.