During his playing days Hill played for Nuneaton Borough, Christchurch United in New Zealand, Northampton Town, Watford and Oxford United. In his time at Northampton, Hill scored 33 league and cup goals in one season, winning the golden boot for finishing as the club's top goal scorer.
Hill was transferred from Northampton Town to Watford for a Fourth Division record fee of £258,000. He was the last signing made by Graham Taylor before his departure from Watford to manage Aston Villa at the end of the 1986–87 season. He did not feature in the plans of incoming manager Dave Bassett and consequently, his stay at Vicarage Road was brief only appearing 4 times: he was transferred to Oxford United for £260,000.
Hill had to finish his playing career early due to a serious knee injury, but having amassed 69 goals from just 171 Football League games.
On 12 September 2012, Hill was appointed manager of Conference South club Eastleigh.[6] In his first season, he led Eastleigh to the Conference South Play Off Semi Finals. At the start of the 2013–14 season Eastleigh were big favourites to win the league. Under Hill's guidance he led Eastleigh to the Conference South title and promotion in the 2013–14 season. The 2014–15 season saw Eastleigh in the Conference Premier, the highest level of football the club had ever competed at, with Hill taking Eastleigh to the Play Off Semi Finals at the end of that season. During his initial spell as manager of Eastleigh, Hill achieved a win ratio of 62%.
Hill resigned at Eastleigh on 23 September 2015 after just over 3 years in the job, following a run of five games without a win, culminating in a 5–2 defeat to Dover Athletic. Leaving the club, Hill said it felt like a break-up, and it was time for a change for both himself and the club.[7]
On 29 November 2016 Hill left Whitehawk and joined Aston Villa to be part of Steve Bruce's recruitment staff.[10] Following the departure of Martin Allen as manager at Eastleigh, after a run of seven games without a win, Hill returned to The Spitfires as Director of Football and caretaker manager on 23 February 2017.[11]
Between May 2018 and July 2020, Hill held the position of Head of Football Operations at Sunderland.[12] He came under criticism from supporters of the club on account of what was perceived as poor transfer business, however received support from owner Stewart Donald whom Hill had previously worked with at Eastleigh.[13]
In March 2023, Hill once again returned to Eastleigh in the role of Club Director.[14] Following the departure of Lee Bradbury in August 2023, he was once again placed in temporary charge of the first-team.[15] On 28 September, he was given the job on a permanent basis.[16]