Simon Wilson’s Blueprint: How Stockport County’s CEO Sparked a Transformation

Simon Wilson’s Blueprint: How Stockport County’s CEO Sparked a Transformation

Simon Wilson - a man who hides above Stockport County’s recent flourishing success in the English Football League.

The former City Football Group director of football has rapidly quickly become a footballing mastermind and one who completely flipped the fortunes of Stockport upon his arrival in 2020.

The Hatters now ply their craft at the top-end of League One, following a gut-wrenching playoff semi-final defeat and a prosperous transfer window this summer.

However, their journey spans a lot further back than just this Spring. Wilson has swapped the Greater Manchester side from non-League sleepers to Championship challengers in just a couple of years’ work. But how he did it is something that remains a lot less flaunted.

A Portfolio to be Proud of

Whilst Stockport County may not be world-beaters just yet, Simon Wilson certainly has experience working in a few previously.

The expert has left multiple roles behind at Manchester City and City Football Group over the years, but coming before that was one of his first jobs at Southampton Football Club as Head of Performance Analysis.

He spent four years on the South Coast before moving 200 miles up north to Manchester, where his time at City commenced with the same job title, just in time for the club’s reimagination under new Abu Dhabi ownership.

17 years ago today, Sheikh Mansour's Abu Dhabi United Group purchased Manchester City in a £200m deal. 💰🔵 pic.twitter.com/HRaMyF3Ukp

— EuroFoot (@eurofootcom) September 1, 2025

Wilson’s seven year tenure in the North West was split into two halves, as he also prised the role of Strategy and Performance Manager in 2010.

As his work became more and more impressive, Wilson then started to look after the entirety of City Football Group, working as the Director of Football Services for Manchester City, Melbourne City and New York City.

That was all before being appointed as Sunderland’s Chief Football Officer in their Premier League relegation year between 2016/17.

Wilson’s consultancy work for the likes of the Premier League, Leicester City, Sparta Prague and AFC Ajax then takes us to 2020 where he joined a then-National League Stockport county as their Director of Football amidst the club’s recent takeover.

Fast-forward five years, Stockport are League One trailblazers and Simon Wilson is now the club’s Chief Executive Officer, after being promoted in February this year.

A Prosperous Plan

So what was installed into Stockport County upon the takeover and Simon Wilson’s arrival?

Mark Scott bought the club as a National League team in 2020, just one season after they had achieved promotion from the National League North. Instantly, the new owner imposed a seven-year plan to reach the Championship.

5⃣ years ago today, owner Mark Stott completed his takeover of the Club - the start of something special 🏆🏆

What's been your favourite moment of the Mark Stott era so far? 🤔#StockportCounty https://t.co/A6nSi3K41k pic.twitter.com/LYUPwjumdr

— Stockport County (@StockportCounty) January 16, 2025

The idea was to put a timeline on Stockport’s success so that they could align it with the correct infrastructure and cash flows needed to enable it. This way, their ambitions could be showcased at every stage through the improvements at the club.

In a recent podcast, Training Ground Guru, Simon Wilson described owner Mark Scott as disciplined and able to trust Wilson and his team to “crack on and do what we (they) think we’re (they’re) experts in.”

Altogether, the system they have orchestrated at Stockport has worked an absolute charm and their seven-year plan still has two years left, as they remain in touching distance of the end goal.

Two Promotions in Five Years

Like most long-term ambitions, you require patience, and that is exactly what Stockport County have demonstrated. Whilst their success has still come fairly swiftly, it’s not as if the promotions have come one after the other.

The new ownership’s first full season in the National League was a heartbreaking one to say the least, but also a very promising one.

The Hatters finished 3rd, which was an incredible achievement considering it was only their second season back in the fifth tier after spending sixth years straight in the National League North.

Their playoff journey soon came to a crashing ending though, as Hartlepool knocked them out of the semi-final eliminator.

The next season spurred even stronger momentum. Stockport won the league with a staggering 94 points and had finally reached the Football League.

🏆 A third league title in five years
🏆 A first EFL title since 1966/67

Stockport County. 𝗖𝗛𝗔𝗠𝗣𝗜𝗢𝗡𝗦!#StockportCounty pic.twitter.com/UT0CDtPJxU

— Stockport County (@StockportCounty) April 16, 2024

However, similarly to their previous stepping stone, Stockport’s League Two journey required two years as well. The first year they finished fourth, but once again found themselves knocked out of the playoffs by Carlisle in the final.

But then County managed to win the fourth tier just one year after in 2024, after gaining 92 points.

Then of course last season, the Greater Manchester outfit finished 3rd, with 87 points in their first campaign in League One, yet lost the playoff semi-final to Leyton Orient via spot kicks.

That brings us to today, where Stockport have entered their second campaign in the third tier, having broken their transfer record this summer through the signing of Malik Mothersille from Peterborough and they obtain a squad more than strong enough to gain promotion automatically.

Furthermore, Simon Wilson has recently been promoted to CEO, where he claims he still is very much involved with the football side of things, but he is now also attempting to boost the club’s commercial revenues.

This is in order to marshal the club’s finances with their rapid progression on the pitch.