Jerry, you are correct about Jerry. He's an insider, as a Director, and Linda Powers approved his purchase of stock as she does as CEO for all insiders who want to buy or sell shares.
The prohibition against insider trading (ie, trading on material, non-pubic information) does not mean a person who is an insider cannot legally trade. Rule 10b5-1 itself lays out some ways it can be legally be done. https://www.law.cornell.edu/cfr/text/17/240.10b5-1.
Just because someone is an insider when they make a trade, it doesn't mean they were in possession of material non-public information when they did so (although they better be prepared to demonstrate that they did not).
There are multiple ways to screen out an insider from possessing material, non-public information so that they can legally buy/sell. More difficult perhaps with a CEO/COO-type position. Perhaps easier with an independent director who is not involved in day-to-day operations .
We don't know all the circumstances surrounding JJs purchase, but just because he did not possess material non-public information when he purchased (or when he decided and committed to purchase, which could be a different earlier date), it doesn't say anything about whether such non-public information existed or whether other individuals in the company were in possession of that information.