Kerr started his career with Newcastle United, but failed to hold down a regular first team place. Despite this, he won three caps for Scotland under the management of Berti Vogts. When Kerr was released by Newcastle in 2004, he signed for his home town club Motherwell. His career then suffered a major setback when he damaged an anterior cruciate ligament in a pre-season friendly, causing him to be out of football for almost nine months. After recovering from his injury, Kerr re-established his place in Motherwell's first-team squad, and he scored his first goal for the club with a spectacular strike in a 4–4 draw with Celtic in 2005. In 2007, Kerr left Motherwell and signed a two-year contract with Hibernian. Kerr scored on his debut for Hibernian against Edinburgh derby rivals Hearts on 6 August 2007. He played regularly under John Collins, but found it harder to hold down a first team place under Mixu Paatelainen and was released on 1 September 2008. It was reported by BBC Sport in September 2008 that Kerr was in signing talks with Major League Soccer club Toronto FC. Kerr failed to agree terms with Toronto and then had unsuccessful trial periods with Brighton & Hove Albion and Oldham Athletic. Kerr told the Daily Record during January 2009 that he may have to end his playing career due to his failure to find a new club since leaving Hibs. Soon afterwards, however, new Inverness CT manager Terry Butcher invited Kerr on trial and he was signed on 2 February. He made his debut for Inverness against former side Hibernian in a 2–0 win and scored his first goal against Hamilton. Inverness were relegated on the last day of the season and Kerr was subsequently released by the club. On 29 June 2009, Kerr signed a contract with Dundee. He scored his first and what turned out to be only goal for Dundee against former club Inverness Caledonian Thistle on 6 March 2010. On 15 October 2010, Kerr had his contract terminated by Dundee due to the club entering administration. Kerr signed for Arbroath in July 2011. At Arbroath he scored once in a 4–2 win over Ayr United. He left the club in 2013.
Coaching career
In June 2016, Kerr was appointed to a coaching position by Albion Rovers. After Darren Young left the club in May 2017, Kerr was appointed first-team manager on 8 May 2017. He had a difficult first season, with Rovers being relegated to Scottish League Two in April 2018, and Kerr decided to leave the club soon afterwards. On 18 May 2018, Kerr was appointed manager of Lowland League club East Kilbride. Kerr resigned his position as manager on 15 October 2018, to become assistant manager of Partick Thistle. Caldwell and Kerr were sacked by Thistle in September 2019.