Chill the mixing bowl, beaters, and heavy cream in the refrigerator for about 10 minutes while you prepare the dry ingredients.
Sift the confectioners' sugar and cocoa powder into a small bowl. Whisk in the espresso powder and fine sea salt until evenly combined.
Spoon 2 tablespoons of the cold cream into a cup and stir with 1 tablespoon of the cocoa-sugar mixture to make a smooth paste; this helps the cocoa dissolve. Scrape the paste into the chilled mixing bowl, then pour in the remaining cream.
Begin whipping on low speed, then increase to medium. Add the remaining cocoa-sugar mixture in 2–3 additions, letting it fully incorporate before the next. Whip until the cream thickens and soft trails form.
Add the vanilla bean paste and continue whipping on medium-high just until medium-firm peaks hold and look glossy, 30–60 seconds more. Avoid overwhipping; if it goes too far, drizzle in a teaspoon of cream and fold gently to loosen.
Refrigerate the finished chocolate whipped cream for 10 minutes to set before dolloping or piping. Serve the same day for best texture.