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In a blender, combine coconut yogurt, soy milk, dates, vanilla, and cinnamon. Blend until smooth.
Pour the blended mixture into a bowl or jar. Stir in chia seeds until well combined.
Transfer into jars or containers and refrigerate for at least 3 hours, or overnight, until thick and pudding-like.
In a small saucepan, stir together maple syrup, cashew butter, and soy milk over low heat for 1–2 minutes until smooth and pourable.
Drizzle the warm caramel sauce over your chilled pudding just before serving. Enjoy!