Hey Jim. The first thing that popped into my head was "why did he leave Southwest in the first place?" And, Look at where JC Penny is right now. Not too sure if I would be hiring an EVP from JCP. I do not understand the move to go outside of SWA for this position. Why not offer it to Mike who has been here for 23 years? Not to knock the other companies but I do not know the history of the other companies that he worked for in an upper officer role.
Nealon left WN in 2006 for greener pastures mainly because he could... There wasn't likely to be any movement that would give him room for growth at WN anytime soon, and when someone comes in with a 6-7 figure salary to go work just up the street, it's hard to ignore.
Nealon left JCP in 2011, which was right around the time their then-new CEO changed how eCommerce was treated. That change was an utter screw-up that took 5 years to reverse, so my guess is he had the sense to get out of the kitchen before the CEO's decision burned down the house. He then came back to WN in a sense, serving as an outside director for six years before taking on the EVP role for innovation.
So, I don't think you can call him an outsider, in that he's got ~12 years experience at the executive and board level with LUV. He's also not a complete insider (like Mike?) in that his resume includes three different marquis companies in the Dallas area. Outside opinions are something the airline culture could use more of -- I'm not a huge fan of promoting people the way that the two policital parties have traditionally chosen Presidential candidates (i.e. longevity and it being "their time").
Ever since this company started going to the outside for hiring Pres., VP, EVP, Directors, managers and even supervisors this company has steadily gone down hill. It all started when Sokol went outside to hire his little buddy from Dal-Fort and look at how he turned out and is no longer here and not by his choice. I actually feel a little sorry for the next CEO that comes in. He will have a lot of work to do to regain the culture, and trust back from the majority of the employees.
News flash: the culture you knew 10 years ago is dead. You're on your third, maybe fourth generation of employees. Nobody currently at WN, be they front line or executive, are ever going to work together in the same way that first and second generation of employees did. The best thing you can hope for at this stage of the company's existence isn't the leader who completely gets and buys into how WN used to work, but instead someone willing to question why things work the way they do, and smart enough to know when it isn't working now.
This is your new normal. Figure it out, or get as far away as you can.