They were relegated from League Two at the end of last season and turned to the former Barnet boss to revive the Spireites in the National League.
But the new era begins on Saturday at a place where few would have chosen to go.
Chesterfield start their bid to reclaim their Football League status at Ebbsfleet United - a side who not only reached the play-off semi-finals last season but have recruited well this summer.
Allen knows the opener isn’t ideal as they bed in to their new surroundings.
But the experienced boss feels victory would send out a powerful message as they look to get off the mark.
“I have got to say it’s a challenging start when you look at the stats,” he said.
“They have had a fantastic two years, winning promotion and doing so well last season to get into the play-offs.
“Ebbsfleet are organised and know how to win matches under a good manager. We know it will be very difficult.
“It’s a tough old place to go and to get anything we have to be spot on in all departments.
“We have to be 100 per cent right and I’m sure we will be.”