Daniel Levy's 'right-hand woman' Donna-Maria Cullen is set to leave Tottenham after holding a seat on the board for 20 years.
The executive director has worked closely with the Spurs chairman, and leaves ahead of a proposed summer shake-up at the club in the wake of their historic Europa League win.
In a statement shared with the club, Cullen said that the decision to depart had been a 'hard one', with Spurs having been her 'life' over the past three decades.
'This has been such a hard decision to make,' Cullen's statement read. 'The Club has been my life for the past three decades.
'I have had the privilege of working with Daniel, whose vision and energy has driven the Club forward, and so many talented and wonderful colleagues.
'It has been quite some journey, starting at White Hart Lane, with a brief stay at Wembley and finally our new home - amazing memories home and away. Ending this season with the Europa League Trophy was a dream come true.
'The time is now right for me to gather more time for myself and my family, whom I thank for all their support over the years. I shall spend the coming months ensuring there is a smooth handover with my staff.
'Thank you all. I wish everyone at the Club all the success in the world.'
Levy also shared that he would 'greatly miss' the support of his associate, writing: 'Donna has made an immense contribution to the Club, over an extensive period. Her diverse responsibilities grew significantly and replacing her roles with a single individual will be impossible.
'While many may associate her primarily with marketing and communications, Donna's impact extends far beyond those areas. Notably, her leadership and political acumen at planning committees, was instrumental in the Club being able to build one of the finest stadiums and training centres in the world.
'She deserves recognition for the contribution she played in the formation of the Tottenham Hotspur Foundation, which has positively impacted countless individuals in our communities, and in establishing the London Academy of Excellence, providing children with exceptional educational opportunities.
'Donna has pushed the conscience of the Club to be at the forefront of environmental and diversity initiatives. She also played a crucial role in supporting the amateur part-time Spurs Ladies, enabling the development of our professional women's team.
'Her daily input will be greatly missed, however she fully deserves to take time for herself, and I know that we shall be able to call upon her advice when needed. We wish her well for the future.'
During the 2024-25 season, Cullen spearheaded the redesign of the club's badge and branding - but more recently focus has shifted to wholesale changes which could happen elsewhere in north London.
Despite leading Spurs to their first trophy in 17 years in Bilbao, Ange Postecoglou's job could yet be under threat after finishing a woeful 17th in the Premier League.
Tottenham are believed to have already held talks with possible successors, including Brentford head coach Thomas Frank.
But Postecoglou broke his silence with a defiant statement, insisting in an interview given on holiday in Greece that winning the Europa League was only the first step for the club.
'I didn't want us to just enjoy the moment,' he said. 'I also wanted us to think about what's next, you know, don't settle for this.
'We've got a taste of it now. My players have got a taste for it. The club's got a taste for it. Well, let's make sure we're back here again.'
Postecoglou has two years left on his contract but admitted before departing for his post-season break that he was unsure whether he would still be in charge for the 2025–26 campaign.