Place the strawberries in a medium bowl with ¼ cup of the granulated sugar and set aside.
Make the cookies: In a small bowl, combine the all-purpose and almond flours. Set aside. Add the butter, brown sugar and remaining ¼ cup of granulated sugar to the bowl of a stand mixer. Mix on medium speed until light and fluffy, about 4 minutes. Add the flour mixture, ½ cup at a time, mixing thoroughly after each addition. Add the salt and vanilla, and mix for 30 seconds to combine.
Turn the dough out onto a cool surface and divide it in quarters. Roll each section into a log measuring about 1 inch thick and 6 inches long. Wrap the logs in plastic wrap and refrigerate until firm, about 1 hour.
Preheat the oven to 350°. Slice the logs into rounds approximately ⅓ inch thick and place them on an ungreased large baking sheet, about 2 inches apart. Bake for 10 to 12 minutes, until the edges appear golden. Place the baking sheets on cooling racks and let cool for 10 minutes.
While the cookies bake, make the whipped cream: Combine the condensed milk and heavy cream. Using a stand mixer fitted with the whisk attachment (or by hand), whip until stiff peaks form.
To finish, crush the cookies and layer the crumbs, strawberries and whipped cream in one large bowl or in individual glasses until full and serve.