Douglas Robb

In February 2018, Robb came to national attention with a blog in which he was critical of millennials, their sense of entitlement, and their lack of grit. He added later "We try as a school not to molly-coddle our students". The Times made a headline out of his comment "If your child is a lazy toerag then I’m going to tell them". His comments aroused widespread criticism, including from former pupils, who responded: "Negative stereotypes of millennials are two a penny and you don’t have to look far to find them [it is] disheartening for anyone to hear, especially from their headteacher." Another former student claimed, "As Gresham’s does cost £34,000-a-year, the headmaster of the boarding school may simply be in a privileged bubble".

At the event marking the end of the Gresham's School academic year 2017–2018, Robb welcomed two old boys of the school as special guests, England rugby stars Tom and Ben Youngs, and the widow of mountaineer Tom Bourdillon, who opened a new outdoor activity centre, with a standard armed forces assault course, a zip wire, abseiling facilities, and a climbing tower.

Robb began his teaching career in Zimbabwe, teaching Economics at Prince Edward School, Harare, from 1994 to 1996. After a severe motorcycling accident in Harare, which led to sepsis, he returned to Britain and was rugby coach at Fettes College in Scotland from 1996 to 1997. He then spent a year at the Moray House School of Education, where he gained a Postgraduate Certificate in Education in Economics, and taught Economics at Loughborough Grammar School for two years, followed by ten years as a Housemaster at Oundle School, where he taught from 2000 to 2010. While at Oundle, he enrolled at the University of Cambridge and gained the degree of Master of Education in 2009. In 2010 he was appointed as Headmaster of Oswestry School in Shropshire, and in September 2014 transferred as head to Gresham's School, Holt, Norfolk.

Douglas Robert Kenneth Robb (born 3 September 1970) is an English schoolmaster who is currently headmaster of Gresham's School. Before that, he was a housemaster at Oundle School and then head of Oswestry School.

Born in the Wirral in 1970, the youngest of his parents' three children, Robb was a choirboy at St Saviour's Church, Oxton, and was educated at Birkenhead School, where he was in the First XV (the school's rugby union team), and then at the University of Edinburgh, where he was President of the Edinburgh University Rugby Football Club and graduated MA in Politics in 1994.