I had the same problem, which I solved by specifying BOTH the classes package AND removing load-on-startup altogether, i.e.:
my-servlet-name
com.sun.jersey.spi.container.servlet.ServletContainer
com.sun.jersey.config.property.packages
my.package.name
I guess because I had more than one servlet under the same package and Jersey coudn't pick the "root" one to be loaded on startup.