1. I'm guessing you're gripping the pick with just the tips of your index finger and thumb. Try to use a bit more surface area of your finger and thumb and hopefully it should stick better, or use your thumb, index and middle finger. Alternatively, go to a music shop and look for a better pick. You can get one made from a more high-friction material so it's easier to grip, or an equilateral one ie. all sides are the same length and all corners are the same angle, so all can be used to strum.
2. Don't use the back of your thumb to strum upwards, use the tip of your index finger. Also, when strumming upwards (with your finger or a pick) you don't need to properly strum it, just lightly brushing the strings on the way up is enough, and you don't even need to hit all of them, depending on which chord you're playing.
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