You say he's had some experience, which doesn't seem to convey something that can be applied to a job. Ruby programmers are high in demand, and some companies even offer bootcamps. I recommend he check those out.
Not sure if it's me, but the different width sizes makes it messy and cumbersome to read. I think it would be a lot more organizes if there was some more order to this. Also, not quite sure what the orange bordered stories means.