So.. As someone who actually applied for the job, I'll give you my pitch. I've been having fun lottery winning type day dreams about this non-stop since the news broke yesterday.
First and foremost, I think what WotC needs to do is try to rebuild the bridge between them and the fans. People love the brands, but hate the company. I would spend a lot of time doing PR work. I'd try and talk to content creators. Admittedly I'd try and focus on ones I feel like would give me soft ball experiences. Focus would be on the fact that I'm a gamer, and I'm trying to steer the ship back into being a company that is made with gaming in mind. I'd call my initiative something dumb like "Fun comes First" or something. Get Chris Perkins to help me run a one-shot for the folks like Ginny D, Bob World Builder, Dungeon Dudes. I'd try to get on Shuffle Up and Play or Game Knights. (Obviously taking my Wyll, Blade of Frontiers EDH deck. Or another commander from one of the D&D sets.)
This would plainly look like a man-child using his executive power to live out all of his gamer dreams. While I would probably be the butt of a lot of jokes, I think that's fine. That's better than the current cold, all business image management current has.
Stock would likely slide early on, because hiring a former car salesman with no c-suite experience is insane. We'd try to claw back as much stock as possible through buybacks while the value was low.
Sadly I think 5.5e is too far along. I would have personally opted to go for a real 6e instead, but since 5.5e is where it's at, I'd be full send on it. I'd focus away from large, hardcover supplements, and go back to smaller, soft cover ones. I would start a new product line on how to be a dungeon master. Small, easily digestible booklets, with video supplements to go with them. Things like "Dungeon Master's First village" or something like that. Maybe even create a character that's like a baby lich, learning the ropes of killing players. Make Mad-Libs style work books that give aspiring DMs a foundation to work off of. Then get people like Jeremy Crawford and Chris Perkins to make videos filling them out prepping for games with them, and then turn those games into actual play videos.
I'd try and re-start Dungeon/Dragon magazine. Probably quarterly at first, and then ramp up. If it even gets close to breaking even we'd go monthly. I'd just do one magazine, and we'd print two small adventures in each one. One would be a stand alone adventure, and the second would be an on-going campaign, published one adventure at a time. If we went monthly the campaign would probably still only get published quarterly and then in months 2, 3, 5, 6, 8, 9, 11, and 12 would be another stand alone adventure. I'd try and fill the rest of the magazine with articles written by people from D&D History, like Ed Greenwood, or Tim Kask.. People working on current D&D products.. And like I mentioned previously, content creators. I think having one article per issue by someone like Questing Beast or the like would help greatly. For one thing, they'd be pushing the magazine for us because obviously they'd want their issues to sell well. Another thing, while it may sound shady, I think it might help overall perception of the brand. These content creators might try and keep us in a positive light hoping to get a spot in a mag.
We're re-printing old product. We'll use the MTG Secret Lair system to print to demand. Offer runs of standard edition (Straight, word for word reprints.) and revised special editions. (New art, notes from people who worked on these projects in the past. Suggestions for using this content in a modern setting, etc.) Take pre-orders and print however much we need. Imagine the "War Chest". A giant set containing all of the boxed editions, and core books from each edition. Bundled together and sold in a mimic treasure chest. It'd be obscene and decadent. Probably costing something crazy like $2500. But it'd probably sell like crazy.
I'd also slow down the MTG train. There's too much product coming out too often. I'd go back to doing set blocks. Two or three sets, all connected to each other in theme and story. And this is going to be drastic, but I'd reboot the story as well. We'll set it hundreds of years after the latest Phyrexian invasion and ret-con it that the machines won. I love Jace, and Chandra, and the others, but they're all out. Their stories have been told. No one cares anymore.
I'd also try again with the 30th anniversary launch. Same product. Old, alpha/beta cards, original art, gold borders. Packs designed for drafting. And I'd print millions of them, and sell them at the standard pack price. I'm in favor of abolishing the reserve list, and I think it would be the right move to stay in line with our "Fun Comes First" MO. However, MTG finance is a huge seller of product, and just wiping out some of these collector's entire net worths overnight would probably be a bad move. With that said, I'd push to lower the price of standard decks. Cards that run like $80/ea on the singles market like Sheoldred would get reprinted in excess. I'd also try to follow the Pokemon model. We'd sell tier 1 Pauper decks for $10. We'd print the top 8 competitive standard decks each year and sell them as pre-cons. They wouldn't be as cheap, but they'd be well under $100. I'd try to position MTG to be as accessible as Pokemon is.
That's it for now. I need to go back to work but I may come add more later