Rod Drury and his ex-partner Anna Stuck are said to have sold two million shares in Xero worth around $313 million.
The block trade was done via Goldman Sachs at A$150 apiece valuing the share parcel at A$300 million, the Herald understands.
Xero shares closed on the ASX at A$148 on Friday putting the share sale at a slight premium to the trading price. Shares in Xero have risen strongly over the past year and are up over 50 per cent.
It's the third sell-down associated with the Drury family in recent years.
In September last year the Rodanna Ventures Trust sold two million shares at A$99 apiece cashing up A$198 million.
The Drury family also sold a block of Xero shares worth around $120m in May 2019.
Xero's 2021 annual report shows as of April 6 Rod Drury and Anna Stuck owned 8.06 per cent of Xero's shares, or 11,914,789.
They were the third largest shareholders behind HSBC Custody Nominees which has 34.01 per cent and JP Morgan Nominees Australia at 20.27 per cent.
Xero made a net profit of $19.8m in the year to March 31, 2021, an increase of $16.4m on the previous financial year.
Total subscribers of its accounting software increased 20 per cent to 2.74 million.
The Herald this month revealed Drury is planning to build a blackened steel and schist rock partially sunken bunker-style 2277sq m home on a picturesque site in between Lake Hayes and Arrowtown.
The property is on the popular rural Speargrass Flat Rd, close to Millbrook Resort and Country Club and The Hills golf course developed by jeweller Sir Michael and Christine Hill.
Drury is the son of a tradesman and an executive assistant who grew up in Hawke's Bay. He stepped down as Xero chief executive in 2018.
Reports say he has retired to the Queenstown area, having left Hawke's Bay and documents submitted to the council showed the applicant for the new house is Duncan Cotterill Nominee (Hawke's Bay) Limited.
But the name R. Drury is also on application documents seeking to extend an existing farm building which is a hay shed, also on the property.
NBR has estimated he has a $1.95 billion fortune.
His land is in the Wakatipu Basin on a 29ha site in the area known locally as the Wharehuanui Hills. House plans submitted the council also label the new home Wharehuanui - whare being house, nui being big.