Jamie came through Kilmarnock's youth academy, producing a man-of-the-match performance in his debut against Hearts on April 7, 2007, going on to establish himself in the first-team during the 2007-08 campaign and becoming a mainstay in the Scotland under 21 side, making 10 appearances. He went on to play 149 times for Kilmarnock throughout his four seasons in the first-team before signing for Hearts in 2011.
After joining Hearts, Jamie got the chance to compete in European football, competing in the Europa League in the 2011-12 season and quickly became the new penalty taker after scoring against Royal Antwerp and St Mirren.
Following the relegation of Hearts in 2014, Kilmarnock re-signed Jamie, where he stayed for a further 2 seasons, before spending a year at Queen of the South and going on to join current club Stranraer in May 2017.
Since joining Stranraer, Jamie has become an important player in the first-team and made over 90 appearances in under 3 seasons at the club.
In June 2021, Jamie was appointed as the clubs new manager after the departure of Stevie Farrell.