Stewart Regan has quit as chief executive of the Scottish Football Association.
The decision comes a week after he failed to land Michael O’Neill, the governing body’s number one target to be the new Scotland manager.
O’Neill opted to remain with Northern Ireland rather than succeed Gordon Strachan.
Regan was also heavily criticised last week for arranging a Scotland summer tour to Peru and Mexico.
Concerns were expressed over player burn out, with the players’ union, PFA Scotland, claiming it was a health and safety issue.
Regan’s resignation comes almost eight years after he took up the position.
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He said in a statement: “I have devoted my time in Scotland to modernising, protecting, developing and promoting the game, whilst facing into some extremely challenging head winds during my time in the job. While it has been tough, I am proud to leave having overseen a period of significant change and substantial growth following the McLeish Report in 2010.
“We are now at another staging point and I recognise that it is now time for further change. I have decided to step aside to allow new leadership to take the organisation forward.
“I would like to thank the staff for their energy, hard work and support during my tenure. Their love of the game mirrors Scotland’s passion for football and I am proud to have served the Association.”
SFA chief operating officer, Andrew McKinlay, will manage the day to day business during the interim period.
Alan McRae, the SFA president, said: “I would like to place on record my thanks and appreciation to Stewart for his commitment to Scottish football.
“He has worked tirelessly and has helped drive through a number of improvements to the governance of the game in the country.
“The search for a new Chief Executive will begin immediately as we will continue to drive Scottish football forward on and off the pitch.”