Blend dates, cashew milk, cashews, cocoa powder, vanilla, salt, and cinnamon in a blender on high speed until very smooth, about 1 minute. Transfer date milk to a quart-size jar or resealable container. Stir in chia seeds. Cover and chill at least 6 hours.
Do Ahead: Chia pudding can be made 5 days ahead. Keep chilled.
Maple Yogurt and Assembly
Stir yogurt and ¼ cup maple syrup in a medium bowl. Transfer to a quart-size jar or resealable container (or reserve yogurt container and use that!).
To serve, alternate layering a few spoonfuls of chia pudding and maple yogurt in a small ramekin or 8-oz. glass. Drizzle with maple syrup and sprinkle with sea salt. Dust with cinnamon.