Graphic design/caricature of a dog character for our brand

We want to move our brand from the current conservative approach to something a little more playful. We want to based it around a dog, one that I have here in the office who is a Bernese Mountain Dog called Milo. We will use the graphics within our app. We want him represented as a young dog, not a puppy but handsome, energetic and fun. To start off a number of poses required. Sitting down, peering over a wall, walking and frontal on back legs.

We are not looking for a one-off, we are hoping that the designer that takes this on will want to continue working with us to develop the dog's character into other areas.

I have numerous photographs of dog to model from but an example is attached.