He [i.e. Paul] entrusted that letter [i.e. Romans] to a “deacon” called Phoebe whose work was taking her to Rome. The letter-bearer would normally be the one to read it out to the recipients and explain its contents. The first expositor of Paul’s greatest letter was an ordained travelling businesswoman.I think this gets some things right and others not.
Firstly on the "right" side: I agree that Phoebe carried Romans; I agree that she was a "deacon" (I could almost envisage this as arising from some sort of "ordination", as it does look like an office of some sort - although not perhaps as formal as this sounds today); I agree that this shows an exceptional level of trust on Paul's part (both practically and pastorally); and I agree that she would have had a role in explaining the contents of Romans (although I'm not sure that "expositor" is a good word for this).
On the negative side it is not the case that letter carriers read letters to recipients. There is no evidence for this in antiquity and there is a load of evidence against it. I think that is plain wrong and argued so in Chicago at SBL last week. (I know it is repeated a lot by NT scholars, but that doesn't mean there is any evidence for it). Further the notion of Phoebe as a "travelling businesswoman" who is going to Rome for her work has only the slenderest basis in the text of Rom 16.1f, which has the typical and deliberate vagueness characteristic of letters of recommendation.
I also agree that the figure of Phoebe, her (imagined) role as "deacon" and her (anticipated) role as letter carrier, are of importance (among a load of other evidence) for considering Paul's view of female Christian leaders (although I don't agree that one can so easily side-step the more negative passages).