Earlier quoted context omitted.
"she wanted to be the Executive Director of WordPress.org for Automattic" But you own and run and finance WordPress.org personally, as you've revealed and talked about numerous times in the last few weeks. I don't follow, how can Heather apply for a job with Automattic to be the Executive Director of a website you personally own?
Automattic employs ~100 people that work full-time on WordPress.org. I can appoint them into positions on WordPress.org, if I think that's appropriate.
So in other words you intermingle for-profit and nonprofit resources for your own private benefit?
Maybe the IRS should be taking a deeper look at WordPress.org's finances?