With all due respect, you couldn't pay me $500k/yr to join Square in any realm regarding information security. From the horror stories I've heard about upper management priorities rapidly shifting and projects abandoned, to engineers stretched so thin on so many projects they they burn out within a year...  it seems like a toxic work environment from the ground up. I hope your new round of security talent can strive to overcome this and increase transparency within the company.
Ask HN: Who is hiring? (March 2018)