He received a bachelor's degree from the Hotelschool The Hague, and then an MBA at the University of Groningen.
He began as a graduate at Amsterdam-based Heineken International NV, the third largest brewer in the world, in 1987. Bolland worked in various international management positions in Africa and Central Europe before joining the Heineken board in 2001. He became chief operating officer in 2005. Bolland has been credited with both building and rolling out the Heineken brand internationally.
In September 2006, he was appointed CEO of the UK supermarket chain Morrisons. Morrisons had acquired Safeway in 2004 creating a 130,000 people strong retail conglomerate in the UK. The merger initially proved unsuccessful. Bolland joined after five profit warnings with a brief to turn round the company.
By 2008 Morrisons had achieved strong growth in both market share and profits, and in 2008, Bolland was announced as The Times "Businessman of the year". Under his guidance, Morrisons "...gained significant market share from rivals".
In November 2009, it was announced that Bolland would become CEO of Marks & Spencer Group PLC. In May 2010, he took over from the then chairman & CEO Sir Stuart Rose. Bolland launched a plan to grow M&S into an international multi-channel retailer. The Evening Standard named Bolland as one of "London's 1000 most influential people" for 2010.
During September 2011, he announced a new look store environment for M&S's UK stores, with a plan to complete the roll out to the entire UK estate by mid-2013. In 2011, M&S returned to France after a 10-year absence and also started the development of a new digital platform that was launched in February 2014.
In 2011, Bolland received an honorary doctorate from York St John University. He was named as "Most Admired Leader" at Management Today magazine's "Britain's Most Admired Companies 2011" awards having been nominated by his peers in the FTSE 100.
In 2014 Bolland was appointed as the Prince of Wales National Ambassador for Business in the Community and in Feb 2015 Bolland joined the board of Coca Cola as a Director.
In January 2016, it was announced that Bolland would be retiring as CEO of Marks and Spencer effective April 2016, and would be replaced by Steve Rowe.
In June 2016, it was announced that Bolland was appointed as a non-executive director of IAG (International Airlines Group).