Chief executive Tom Lawrence and head of football John Still are to leave Southend United as part of a restructure of the National League club.
Former Peterborough United and Luton Town manager Still will depart with immediate effect, while Lawrence will stay on until the season is over – both were appointed five years ago.
First-team coach Jason Demetriou, a Cyprus international who also played over 240 games for the Shrimpers, will also leave when his contract expires in the summer and there will be redundancies among non-football staff.
The club are creating director of football and general manager roles which they say will result in "clearer accountability, improve operational efficiency and strengthen the foundations around both football and non-football operations".
Southend were taken over in the summer of 2024 by a consortium headed by Australian businessman Justin Rees, nine months after former owner Ron Martin had put the club up for sale.
And the consortium, Cosu (Custodians of Southend United) abandoned previous plans to relocate to the Fossetts Farm area, confirming that the club would remain at Roots Hall.
The restructure announcement comes at a time when Southend are pushing to reach the play-offs for the second season – Tuesday's 2-1 win over Yeovil Town leaving Kevin Maher's team seventh in the table.
And supporters also have a trip to Wembley to look forward to after beating Southport 3-1 last weekend to secure a place in the FA Trophy final.
"Anything we do that distracts from [what is happening] on the pitch, we would do it reluctantly," chairman Rees told BBC Essex when asked about the timing.
"This process that's led to the restructure has taken a while, as these things do, It's not the sort of thing you can neatly do in an off season.
"Once we were clear on the direction we wanted to travel what became important then was to move forward and ensure that if there is any disruption – which we do our best to minimise – it doesn't spill out into a second season."
The club say the appointment of the new director of football is likely to happen "imminently" and there will also be a head of recruitment joining.
The process to select a general manager – who will run the club's non-football operations day to day – is only just getting under way.
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Lawrence has been part of Cosu since the takeover of the club was completed.
"More than just being CEO, Tom's on the board as well and obviously part of all the discussions we have – we all exchange our views, we're a seven-person board so there are diverse views, and then ultimately we come to a singular decision of what the board wants to do," said Rees.
"The starting point for us wasn't about people, individuals, it was about structure and a big part of that is we do want to move from a structure where lots of people reported to a single leader to [one where we] split the business in half and have a football person leading football and a general manager with a more focused remit on commercial and media.
"We've trimmed in some areas to allow for investment in others and there's different reasons why some people are leaving and some are staying."
Southend made a pre-tax loss of £2.65m in 2024, set against a £2.5m turnover, but their annual report for last season has yet to be published via the Companies House website.
Rees said the changes being made by the club were "not a cost-cutting exercise" although they would "unashamedly" spend less money if there were areas and opportunities to do so.
"Everyone knows our financial situation. We've been very open that we need to improve it," he continued.
"Sometimes that can be about trimming in certain areas, but of course, we've invested in other areas as well."
Rees said Southend were "a people business" and having to let staff go was "the most difficult part" of the process.
He added: "We don't make any of these changes lightly and we've had people that have served us for decades.
"When we started the process there were half a dozen roles that were earmarked for changing.
"The exact number changes from where you start to where you finish but there are a few departures and the people departing have served the club well for a long time and we truly are grateful for their contribution."
