Cut butter into chunks. Using the whip attachment, whip butter several minutes, scraping down occasionally, until butter has increased in volume and lightened in color.
Add half of the powdered sugar and mix on low-speed until incorporated, again stopping to scrape down. Add the vanilla extract and mix to combine.
Add the rest of the powdered sugar and beat on low-speed until sugar is incorporated, again stopping to scrape down as needed. Increase speed to medium-high and beat for 2 to 3 minutes.
Turn back to low and add the heavy cream by the tablespoon, starting with a tablespoon or two, then adding more if needed. Turn mixer up to medium-high and whip until light.