My hunch is that Jack won't/can't stick around for three reasons :
a) He has another company to save which is in itself a
full time job, given how hot the payments space is.
b) If Twitter should ultimately (and rather ingloriously)
be sold to say a Alibaba or Facebook or (longshots)
Microsoft or Google, Jack wouldn't want to be the guy who
'trimmed the fat' and right-sized it for a sale. It wouldn't
be good for his personal brand.
c) Twitter hasn't yet found an identity - even with
300 MM users (even Costolo hasn't contested this as
recently as May, in an interview [1]). Jack can only
breathe life into it, if he makes one hell of a pivot away
from the way Twitter is perceived by the masses - way
too confusing to use for most [2] and lacking an identity
(People still ask of Twitter what they don't of Facebook -
what Twitter will be when it has finally grown up)[3]
Bonus reason : Twitter has gone through 5 product heads
in the five years while Costolo was at the helm. A part
of me wants to believe that it is not all the fault of
Costolo and that Twitter needs a fundamental rethink.
I doubt Dorsey is willing to do it. I just don't think
he can, unless he gives up his gig at Square.
[1] [3] Twitter CEO Dick Costolo Q&A: What to Do When People Say ‘You Suck’
