"he should probably focus his efforts earlier in the pipeline"
That's the best and only truly relevant point to the outcome he's hoping for right there. Go after schools, go after school boards that don't make technical proficiency a priority, go after parents who don't know the value of science and tech.
Jackson has and always will go to the money-men. Why? I don't know for sure so I'd rather not speculate, but the inferences to be made from such moves aren't flattering to him.
Money matters aside, it's been about 5+ years since he had anything relevant to say, it's about time for him to be latching on to a cause again. If we're being hyper-cynical, the timing in relation to the recent awareness campaign on behalf of women-in-tech produced in him a lightbulb-moment that is otherwise uninspired and downright predictable.