Gerard Lyttle believes David Healy could be tempted to leave Linfield this summer and have a crack at management across the water.
Healy's stock is on the rise after guiding the Blues to a 56th league title.
The former Northern Ireland striker has now won five Gibson Cups since becoming manager in 2015, including four on the bounce.
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The emphatic run also includes two doubles.
Healy was reticent about what his future holds at Windsor Park after celebrating another trophy success at the weekend, but speculation continues to mount over whether he will be in the Linfield dugout when the new season comes around.
And Northern Ireland Under 17 and 19 manager Lyttle wouldn't be surprised if Healy exits South Belfast for a job in England or Scotland.
"David has won so much in the game, so maybe the time is now for him to jump and leave the club in a really good position, and have a crack at full-time football across the water," Lyttle told Belfast Live's That's What I Call Football podcast.
"David will want to go and test himself. He is a winner.
"He will want to go and test himself and see if he is good enough to do it in England or Scotland. David is a big name in England, a lot of people know him and he is a record-breaking Northern Ireland centre forward.
"He will have a lot of good friends and contacts he can tap into in England. So I don't think he will fear anything. He will relish the challenge.
"And if it doesn't work, he can come back home.
"So I think, personally, if I am David Healy, now is the time to make the move. David is a very calculated individual and he will only make the right move for him.
"I am seeing people like Stephen Bradley at Shamrock Rovers being linked with Lincoln who are a massive club with a massive budget Somewhere like that would be great for David.
"I don't think David would leave Linfield for a job that would potentially see him sacked in six months. It will be a well thought-out process."
Healy voiced some frustration after Saturday's title win, admitting he will never win over some Linfield supporters.
Despite winning four Gibson Cups on the bounce he says there is a minority who remain unconvinced by the 42-year-old's managerial ability.
Lyttle says those fans "should be careful what they wish for".
He added: "Going by his interview on Saturday he was frustrated and annoyed by a small section of Linfield fans who don't give him the credit he deserves. And he's right.
"I saw some of the comments afterwards with some fans saying 'it's still time to go, David', which is unbelievable.
"It is one of them ones, be careful what you wish for. That would be my advice to Linfield fans. What he has achieved in his time at Linfield is unbelievable.
"Let's remember he came into the job wth a lack of managerial experience, and he's now got all the experience in the world. He is more than capable and more deserving of a shot across the water.
"He knows how to win league titles and develop young players. So he ticks a lot of boxes.
"I would be gutted to see him leave the Irish league, because I think he is great for it."
On-loan striker Chris McKee arrived at Windsor in January and went on to score six goals in 16 appearances for the Blues, including one in Saturday's 2-0 win over Coleraine to clinch the title.
He also believes Healy could be lured into a move across the water.
"David is very calm and measured inside the changing room. He has been brilliant with me since I came in, as he has with all the lads," McKee said.
"And if he does get his chance to go across the water, I believe it will be an opportunity he won't turn down.
"I think he will relish the challenge.
"But obviously for me, as a Linfield fan and currently a Linfield player, if he stays then it will be a good thing for the club.
"He will know what his options are and what is best for him. All I can say is that I have loved working under him for the past six months and I hope he stays."
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