The head of the UK retail division has been approached by Friends Provident as well as other financial firms as his credentials are viewed as nothing short of impeccable.
According to his colleagues, Mr Matthews wants to succeed current Stan Life chief executive Sandy Crombie, who will be 60 in just over a year's time, but could be tempted by a top job at Friends in the meantime.
Whatever his feelings on a personal level, the speculation over his position is unsettling to analysts and investors.
Shares in Standard Life have fallen 28 per cent over the last six months, which could be directly attributed to a lack of confidence and uncertainty about the potential move.
"What is going on at the top is unsettling," Roman Cizdyn, analyst at Oriel Securities told Bloomberg.
"It all looks very messy up there," a shareholder added.