After leaving Peterhead in the summer of 2007, Macaulay was out of football for a few months until he signed for Alloa Athletic after a successful trial period.

[2] He continued playing semi-professional football in the Scottish League system until 2012, when he graduated from the University of Stirling.

[2] Macaulay began in a non-playing role in Sweden shortly afterwards, working as a performance analyst at Östersunds for Graham Potter, where he spent six years.

[2] Macaulay joined Swansea City in a similar role in June 2018, when Potter moved to the Welsh club.

[7] Macaulay left Chelsea to become head of recruitment for West Ham United in January 2025, once again reuniting with Potter.