Gordon Smith has left his post as chief executive of the Scottish Football Association for personal reasons.
The former Rangers midfielder took up the post in 2007, having formerly worked as a BBC Scotland sports pundit.
In a statement, the SFA said: "Gordon Smith has resigned from his post as chief executive. A further statement will be issued tomorrow."
Smith played for Kilmarnock, Rangers and Brighton, while he had a spell as assistant manager with St Mirren.
But Smith was better known as a regular voice on BBC Scotland's football programmes Sportsound and Sportscene.
He also owned a players' agency but gave up both interests when he took up the role at Hampden after agreeing to succeed David Taylor.
When he took up the role in June 2007, Smith said he was prepared for the flak that would undoubtedly come his way.
Barry Ferguson and Allan McGregor were punished for their indiscipline
"I think it was the American philosopher and writer Elbert Hubbard who said the only way to avoid criticism was to do nothing, say nothing and be nothing," the chief executive said at the time.
"That's how you avoid criticism and certainly this job is not about avoiding criticism."
His near three-year reign was not without its fair share of controversy.
Smith was part of a four-man SFA panel which appointed George Burley as manager in January 2008.
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However, the SFA came in for fierce criticism over its handling of the interview process, with Mark McGhee, Tommy Burns and Graeme Souness also in the frame to succeed Alex McLeish.
Smith used the media conference parading Burley to respond to the SFA's critics.
"It has been astonishing people saying: 'What is the point of interviewing for the job?'
"You are all asking questions, don't you think it was appropriate that we asked questions in terms of what George was going to do?"
Scotland, under Burley, failed to qualify for the 2010 World Cup finals and the campaign was overshadowed by the infamous Boozegate scandal.
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Give your reaction to Gordon Smith's resignation
The SFA ended the international careers of Rangers pair Barry Ferguson and Allan McGregor, after they were involved in a drinking session after the defeat by the Netherlands and made V-signs on the bench against Iceland.
Ferguson and McGregor apologised for their actions, but Smith subsequently cast doubt on the nature of their bans and hinted their international careers could be resurrected under a future Scotland manager.
Burley won just three of his 14 games in charge, and, despite receiving a vote of confidence after their failed World Cup qualification campaign, he was sacked in November 2009.
A month later, the SFA appointed Dundee United manager Craig Levein as the new Scotland boss, with Smith insisting Levein was its unanimous choice.
"When we appointed George Burley, we obviously felt George could succeed," Smith said at the time of Levein's appointment.
"It's the same aspect with this appointment too, because we do think Craig is the right person for the job."
I thought Gordon was an inspired appointment and I still think that, given time, he would've got things going
Former Scotland manager Craig Brown
The SFA chief executive oversees the development of football in Scotland and the administration of disciplinary matters, but is also responsible for the general organisation of the national side.
And former Scotland manager Craig Brown insists Smith was an impressive chief executive.
Brown, now in charge of Scottish Premier League outfit Motherwell, told BBC Scotland: "I'm astonished actually because I thought Gordon was settling in well.
"It's a difficult job and I was 16 years working for the SFA and working under three different chief executives.
"They all had their qualities but I thought Gordon was an inspired appointment and I still think that, given time, he would've got things going."
SPL chief executive Neil Doncaster said he was "absolutely flabbergasted" at the news.
"I didn't see that coming at all," he added. "I would like to wish Gordon well for the future.
"Since I arrived last summer, I have really tried to build relationships between the SFA, the SFL and ourselves.
"That will continue going forward."
The former Rangers midfielder took up the post in 2007, having formerly worked as a BBC Scotland sports pundit.
In a statement, the SFA said: "Gordon Smith has resigned from his post as chief executive. A further statement will be issued tomorrow."
Smith played for Kilmarnock, Rangers and Brighton, while he had a spell as assistant manager with St Mirren.
But Smith was better known as a regular voice on BBC Scotland's football programmes Sportsound and Sportscene.
He also owned a players' agency but gave up both interests when he took up the role at Hampden after agreeing to succeed David Taylor.
When he took up the role in June 2007, Smith said he was prepared for the flak that would undoubtedly come his way.
Barry Ferguson and Allan McGregor were punished for their indiscipline
"I think it was the American philosopher and writer Elbert Hubbard who said the only way to avoid criticism was to do nothing, say nothing and be nothing," the chief executive said at the time.
"That's how you avoid criticism and certainly this job is not about avoiding criticism."
His near three-year reign was not without its fair share of controversy.
Smith was part of a four-man SFA panel which appointed George Burley as manager in January 2008.
Cannot play media.You do not have the correct version of the flash player. Download the correct version
However, the SFA came in for fierce criticism over its handling of the interview process, with Mark McGhee, Tommy Burns and Graeme Souness also in the frame to succeed Alex McLeish.
Smith used the media conference parading Burley to respond to the SFA's critics.
"It has been astonishing people saying: 'What is the point of interviewing for the job?'
"You are all asking questions, don't you think it was appropriate that we asked questions in terms of what George was going to do?"
Scotland, under Burley, failed to qualify for the 2010 World Cup finals and the campaign was overshadowed by the infamous Boozegate scandal.
MY SPORT: DEBATE
Give your reaction to Gordon Smith's resignation
The SFA ended the international careers of Rangers pair Barry Ferguson and Allan McGregor, after they were involved in a drinking session after the defeat by the Netherlands and made V-signs on the bench against Iceland.
Ferguson and McGregor apologised for their actions, but Smith subsequently cast doubt on the nature of their bans and hinted their international careers could be resurrected under a future Scotland manager.
Burley won just three of his 14 games in charge, and, despite receiving a vote of confidence after their failed World Cup qualification campaign, he was sacked in November 2009.
A month later, the SFA appointed Dundee United manager Craig Levein as the new Scotland boss, with Smith insisting Levein was its unanimous choice.
"When we appointed George Burley, we obviously felt George could succeed," Smith said at the time of Levein's appointment.
"It's the same aspect with this appointment too, because we do think Craig is the right person for the job."
I thought Gordon was an inspired appointment and I still think that, given time, he would've got things going
Former Scotland manager Craig Brown
The SFA chief executive oversees the development of football in Scotland and the administration of disciplinary matters, but is also responsible for the general organisation of the national side.
And former Scotland manager Craig Brown insists Smith was an impressive chief executive.
Brown, now in charge of Scottish Premier League outfit Motherwell, told BBC Scotland: "I'm astonished actually because I thought Gordon was settling in well.
"It's a difficult job and I was 16 years working for the SFA and working under three different chief executives.
"They all had their qualities but I thought Gordon was an inspired appointment and I still think that, given time, he would've got things going."
SPL chief executive Neil Doncaster said he was "absolutely flabbergasted" at the news.
"I didn't see that coming at all," he added. "I would like to wish Gordon well for the future.
"Since I arrived last summer, I have really tried to build relationships between the SFA, the SFL and ourselves.
"That will continue going forward."
