The Scottish Football Association has announced that Stewart Regan has stepped down as chief executive following an eight-year spell.
The decision comes during the FA's hunt for a new manager for the Scotland national team, which has proved problematic.
Northern Ireland head coach Michael O'Neill was a contender to replace Gordon Strachan, but he ended up rejecting the job offer in favour of keeping his current role.
Within the Scottish FA's announcement, Regan said: "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."
Chief operating officer Andrew McKinlay will take over the day-to-day running until the Association finds a replacement.
