Place the sliced pears in a bowl with 1 tablespoon of brown sugar, 1 tablespoon of cornstarch, and 1 teaspoon of chai masala spice blend. Toss gently to combine. Set aside.
Make the caramel:
Preheat the oven to 350ºF. Lightly grease a 9-inch cake pan. Set aside.
Pour the heavy cream into a heat-proof measuring glass. Microwave on high for 45 seconds until hot and bubbly. Add the masala chai blend and steep for 5 minutes. Set aside.
Melt 4 tablespoons of butter in a small pot over medium heat. Once melted, add ½ cup light brown sugar. Stir to combine. Cook over medium heat for 2 to 3 minutes, stirring occasionally, until the sugar dissolves and the mixture darkens slightly in color. Remove from the heat. Pour the heavy cream through a sieve into the caramel mixture. Whisk until completely smooth.
Pour the mixture into the prepared cake pan and smooth it into an even layer. Transfer to the refrigerator for 15 minutes.
Make the batter:
Sift ¾ cup cake flour, 1 teaspoon chai masala, 1 teaspoon baking powder, and ¼ teaspoon kosher salt into a small bowl. Set aside.
Add 4 tablespoons of butter and ½ cup light brown sugar to a large bowl. Use an electric hand mixer to cream the butter and sugar until light and fluffy. Add 1 egg and mix until smooth.
Add half the sifted dry ingredients and beat with the mixer until just combined. Add half the milk and beat until incorporated. Add the remaining dry ingredients and the remaining milk, along with 1 teaspoon vanilla extract. Beat until just combined. Don’t over-mix!
Assemble the cake:
Remove the cake pan from the refrigerator. Pour the pears over the caramel. Pour the batter over the pears and carefully smooth it into an even layer.
Bake the upside-down cake:
Transfer the cake to the oven for 35 to 40 minutes or until a toothpick inserted into the center of the cake comes out clean.
Let the cake stand for about 30 to 45 minutes at room temperature.
Invert the cake:
Place a large plate over the cake pan and carefully flip the cake onto the plate. Use a small butter knife to tap over the pan to encourage the release of the cake.
To serve:
Slice the cake into pieces and serve with whipped cream and a sprinkle of cinnamon on top, if desired.