Having a puppy is often just like having a baby: Potty training and lack of sleep go hand in hand. Rather than having Cricket set your routine, take charge and create a routine for him.
If Cricket is just taking a nap in his crate during the day, there's no need to wake him up as long as you take him to his potty area as soon as he wakes up. He'll likely want to urinate about half a minute after waking up, and to poop shortly after that. Before going to sleep at night, take Cricket to go potty one last time and avoid giving him water about two and a half hours before bedtime, because this might worsen his urge to go.
Cricket's age greatly determines whether you'll be waking him up in the middle of the night to go potty. Use your puppy's age in months to determine how many hours he can hold his bladder. If your puppy is younger than 3 or 4 months of age, set your alarm at nighttime so you can wake him up halfway through the night and take him to go potty, because at this age he might not be able to make it through the night. Older puppies are more likely to sleep about seven hour without having to eliminate.
When you wake Cricket up to go potty, make it all about business. Avoid turning on bright lights and making a lot of noise, because he might think it's time to wake up and play. Just take him to his designated potty area and calmly tell him "go potty." Always use the same command so he associates it with doing his business. When he goes potty, praise him quietly, and then place him back in his crate and go back to sleep.
Making your puppy sleep in a crate can help the housebreaking process, because dogs instinctively won't soil areas where they sleep. If Cricket does soil his crate in the middle of the night, set your alarm to wake up an hour earlier so you can make him go potty in the right area before he has an accident. Clean the crate with a commercial pet stain cleanser to eliminate the scent, because it might make Cricket want to soil in the same area again.