Stuart McConnachie, 48, who was appointed regional manager for London and the South-east in June 1996, is the latest to leave.
He follows his immediate superior, London and South-east director Stuart Fraser, and managing director David Anderson out the door at the privately owned contractor. McConnachie was responsible for building the London operation into a £50m-turnover business.
A Shepherd insider revealed that his resignation was a blow to the company: "It came as a real shock to everyone. He was well-respected and he brought a lot of business to Shepherd Construction." A rival contractor speculated: "You've got to wonder what's happening when a business loses so many senior people so quickly. A lot of people are curious to know what's going on." But McConnachie said his departure was not directly related to that of Fraser and Anderson.
"It is true the changes meant that the two people I reported directly to have left. But it was not directly related to me leaving.
"We have parted company on amicable terms. I felt that the job I joined to do was finished. I am going off to pursue other interests." McConnachie added that the possibility of his leaving had been under discussion with Shepherd for some time, and denied that the three departures would hurt the company.
"Shepherd is a big organisation. Lots of big organisations shed senior staff and continue to prosper." A Shepherd spokesman said: "Stuart McConnachie has left Shepherd Construction today after working for the company for three years. He now feels the time is right to pursue other interests." The spokesman said there was no link between McConnachie's departure and those of Anderson and Fraser. He denied that there was any difficulty with the exodus of senior staff.
"It's a very fast-moving industry. Changes in larger companies happen quite frequently." McConnachie was given the brief of building up the York-based business' interests in London when he joined in 1996.
"Considering that before I joined, Shepherd did no business in London and now it turns over more than £50m, I feel I have done my job."