Grease an 8x4 inch loaf pan with butter or coconut oil, then line it with parchment paper.
Make the cookie layer by stirring together the almond flour, butter, maple syrup, and salt in a medium bowl until well combined, then press the mixture evenly into the bottom of the prepared pan.
Back in the same bowl, make the filling by stirring together the almond butter, maple syrup, vanilla, and salt until smooth. (If the mixture is stiff, you can microwave it using 15 second increments, stirring in between, until it softens and becomes spreadable.) Spread the caramel mixture on top of the cookie layer.
Use your hands to flatten the dates into thin, oblong discs that are just about the width of the pan. Arrange the dates evenly on top of the almond butter filling, and press them into the filling.
Melt the chocolate in the microwave, stirring every 15 seconds, OR in a heat-safe bowl set on top of a pan of simmering water.
Pour the chocolate over the filling, and use a spatula to gently spread the chocolate so that the entire surface is evenly covered. Sprinkle with flaky salt. Refrigerate the pan for 20 minutes, until the chocolate starts to firm up.
Loosely cover the pan with plastic and freeze it for at least 4 hours and up to overnight.