He founded and was director of Operation Black Vote (OBV) and Trustee of the charity Police Now, and has been Principal of Homerton College, Cambridge, since October 2021.

Woolley was born to Lolita, a Windrush generation nurse in Leicester in the East Midlands of England on 24 December 1961,[3] and aged two, she sent him to a Catholic orphanage.

[6] Woolley left school without any A-Level qualifications and started his working life in an apprenticeship[7] as a car mechanic.

[8] He moved to London at the age of 19[6] and spent four successful years in advertising, employed by The Rank Organisation in Wardour Street, before deciding to study Spanish and Politics at Middlesex University.

[7] He started to research the potential impact of a black vote, which he argued could influence electoral outcomes in marginal seats.

[18] He worked with Bernie Grant, Al Sharpton, Naomi Campbell and Jesse Jackson on grassroots campaigns highlighting racial discrimination.

[7] In 2017, Operation Black Vote, The Guardian newspaper and Green Park Ltd launched the Colour of Power, which to date is the most in-depth look at the racial make-up of Britain's top jobs across 28 sectors that dominate British society.

[19] The results were reported in The Guardian: "Barely 3% of Britain’s most powerful and influential people are from black and minority ethnic groups, according to a broad new analysis that highlights startling inequality despite decades of legislation to address discrimination".

[21] In May 2019, Woolley and Operation Black Vote launched a ground-breaking report into more than 130 key local authorities that emphasised the lack of BME representation.

[34][35][36][37] In July 2023, Woolley was a guest on BBC Radio 4, Desert Island Discs and spoke of his love for his teenage son Luca and their shared musical tastes.

"[7] Woolley was nominated for a life peerage to sit as a Crossbencher in the House of Lords by Prime Minister Theresa May in her 2019 Resignation Honours List.