This is all part of a plan that was laid down some time ago.
Jack is a product guy. Tremendously good (evidence being he created both Twitter and Square). Jack is not an operator of a quickly scaling company, or at least, that's what Ev has said on the record more than once.
Jack recognizes his strengths and weaknesses. At Twitter his weaknesses were "recognized" for him and he was pushed out as CEO. It was painful and left some damaged bridges. He's been maturing and growing since then and looking back, probably agrees it was the right move even if it was handled the wrong way.
Then he founded Square. He got the product launched and hired Keith Rabois, a well-known operator. A hardcore, real operator and business guy.
Jack will run product at both companies. Keith will run day to day operations at Square, probably even as CEO. DickC will continue to run day to day operations at Twitter. Jack will play to his strengths and let someone else keep the cash balances in check.
With Twitter, Jack was pushed out. With Square, he probably couldn't have hired Keith if there wasn't a plan or timeline in place for Keith to become CEO.
I doubt Keith Rabois joined because he felt he could become CEO. I think you're underestimating the draw of getting to work with someone as good as Jack Dorsey and on a product as exciting (to Keith) as Square.
Jack is a product guy. Tremendously good (evidence being he created both Twitter and Square). Jack is not an operator of a quickly scaling company, or at least, that's what Ev has said on the record more than once.
Jack recognizes his strengths and weaknesses. At Twitter his weaknesses were "recognized" for him and he was pushed out as CEO. It was painful and left some damaged bridges. He's been maturing and growing since then and looking back, probably agrees it was the right move even if it was handled the wrong way.
Then he founded Square. He got the product launched and hired Keith Rabois, a well-known operator. A hardcore, real operator and business guy.
Jack will run product at both companies. Keith will run day to day operations at Square, probably even as CEO. DickC will continue to run day to day operations at Twitter. Jack will play to his strengths and let someone else keep the cash balances in check.
With Twitter, Jack was pushed out. With Square, he probably couldn't have hired Keith if there wasn't a plan or timeline in place for Keith to become CEO.
* This is all my speculation.