Preheat oven to 350° and grease a large baking dish with cooking spray. In a large skillet over medium high heat, heat olive oil. Add sausage, breaking up the meat with a wooden spoon, and cook until meat is golden and cooked through, about 5 minutes. Remove from heat and drain cooked sausage on paper towels then transfer to a large bowl.
Add cream cheese, cheddar, and 1 tablespoon chives. Season with freshly ground black pepper then mix until well combined.
On a cutting board, flatten a biscuit round into a thin flat circle (about ¼” thick). Spoon about a tablespoon of the sausage and cheese mixture into the center then wrap the dough around the mixture. Pinch to seal. Place seam side-down in prepared baking dish. Repeat with remaining biscuit rounds.
Brush the tops of the biscuits with melted butter then sprinkle with garlic powder and remaining chives. Grind more pepper on top.
Bake until biscuits are golden, 10 to 15 minutes. Serve warm.