After graduating, Street harboured ambitions to be a social worker, but he was turned down by Birmingham City Council. He was also famously turned down for the Marks & Spencer training scheme. Street thus started his career at the John Lewis Partnership in 1985 as a trainee at Brent Cross. After roles in department stores, head office and manufacturing units, Street became managing director of John Lewis Milton Keynes in 1993, moving to the same role at Bluewater five years later. In 2000 he became supply chain director and then, two years later, director of personnel. He became managing director in 2007 and, during his tenure at the top, oversaw a 50% increase in gross sales to over £4.4 billion, a doubling in the number of stores and the growth of the company's online sales department, in spite of the Great Recession.
Political career
Mayoral election
On 29 September 2016, Street was officially selected by Conservatives to stand in the first election for Mayor of the West Midlands Combined Authority, which took place on 4 May 2017. Street said: " will determine how we create wealth here and what type of society the West Midlands will become. I promise to work tirelessly to convince voters that I am the man to lead us through these decisions... Our economy is being renewed but we have much more to do to ensure everybody feels the benefit. Our mission is therefore to build the economic powerhouse of Britain in an inclusive way. That will need leadership from somebody who has a proven record, can bring people together and can represent us with passion. This election needs to go beyond traditional political loyalties and I look forward to seeking voters' support for the job ahead." The following day, it was confirmed that Street would leave John Lewis at the end of October 2016. He was succeeded by Paula Nickolds, who assumed the role in January 2017. In a speech at the 2016 Conservative Party conference, Street declared his support for Birmingham's bid to host the 2026 Commonwealth Games. He also announced that he would seek to address the "imbalance" in transportation spending that sees London receive seven times as much spending on transport infrastructure per head as the West Midlands does. Street said that fighting inequality would also be a priority, as "social challenges can only be met when everybody shares the fruits of economic progress", saying that he would draw on the lessons of Joseph Chamberlain and his own experiences with the John Lewis Partnership, which shares profits with all of its employees. He also called for a series of debates with Labour candidate Siôn Simon and Liberal Democrat candidate Beverley Nielsen. Street was endorsed by The Lord Jones of Birmingham, a businessman and crossbench peer who formerly served as Minister of State for Trade and Investment under Gordon Brown. Street was elected Mayor of the West Midlands on 4 May 2017 with 238,628 votes in the second round of voting, and in October of the same year was placed 82nd on commentator Iain Dale's list of 'The Top 100 Most Influential People on the Right'.
Political views
Street has been an outspoken critic of continually-rising business rates, arguing that "property is the way retailers have made money historically and we need a system that is a reflection of the future", though he does not believe that online transaction taxes are the answer.
For more than 20 years from his school days, Street was involved with the charity Birmingham Young Volunteers Adventure Camps, taking underprivileged children nominated by Birmingham Social Services to Wales for adventure camps. Street is a supporter of Aston Villa F.C. and runs half-marathons. He is Vice-Chairman of Performances Birmingham Limited, which is responsible for running the city's Symphony and Town Halls. Street is openly gay. He is a close friend of the Conservative MP Michael Fabricant.