The Enquirer revealed last week that managing director Phil Greer had left the family-owned contractor after 35 years with the firm.
It is now believed that southern division managing director Mark Tant has also left the business.
Tant was recruited from Willmott Dixon two and a half years ago to lead the southern expansion of Shepherd after it opened its London office at the start of 2011.
The latest departure comes as Shepherd Group revealed it had rejigged the senior management team at Shepherd Construction.
Andrew Constantine, who was previously regional director in the east will now assume the role of national operations director, effectively taking on the extra southern region post vacated by Tant.
Former group operations director for engineering at Shepherd Steve Collins becomes executive director of operations, reporting directly to Group Built Environment ceo Mark Perkins.
Gary Walton as executive commercial director and Gary Edwards, executive director of development complete the new management team.
A Shepherd Construction spokesperson said: “We have restructured our management team to ensure Shepherd Construction has the right leadership team in place to take the business forward.
“The underlying business in Shepherd Construction is in good shape with strong processes, a great order book, a strong pipeline and many profitable projects. As such, we are well placed to take advantage of the opportunities ahead as markets recover.”