A trust associated with Rod Drury and his ex-partner Anna Stuck is selling two million shares in Xero.
Goldman Sachs is handling the trade.
The shares are being offered at A$99, a 3.9 per cent discount to the Wednesday's closing price of A$103.00 - a fresh all-time high for the stock, which has risen by 30 per cent this year.
At that price, the shares would be worth A$198 million ($204m).
The Drury family also sold a block of Xero shares worth around $120m in May last year.
Xero's 2020 annual report listed the Drury family's Rodanna Ventures Trust as the largest individual shareholder, with 15.7 million shares, representing an 11.08 per cent share in the company worth just under $1.7 billion.
While its founder is selling down, Xero also disclosed late yesterday that new chairman David Thodey is backing up the truck. Thodey bought shares worth A$405,000 as he picked up a block of 4000 at A$101.34 on August 31, doubling his existing stake.
Xero, which squeaked into the black with a $3.3m profit for FY2020 as revenue rose by a third to $718m, now has some heady multiples.
But Harbour Asset Management portfolio manager Shane Solly thinks the company - which recently updated that subscriber growth has continued through the pandemic, if at a slower pace - can go higher.
"Xero remains one of our larger active investments," he says.
"Covid-19 may have accelerated the move to online SaaS [software-as-a-service or 'cloud'] for a number of services including accounting. Xero may also have a bigger part to play in wider financial sector disruption."
Last week, Xero flagged a push into lending as it bought fintech startup Waddle in a deal worth up to $80m.
Waddle lets a small business take a quick secured loan against its accounts receivables - helping to tide it over until an invoice is paid.
In a market filing, Xero indicated the move could be part of a broader push into financing.
"Post the acquisition of Waddle, Xero will continue to explore how to facilitate small business access to capital beyond invoice financing," it said.
Departing Pushpay boss sells half his stake
Meanwhile, departing Pushpay chief executive Bruce Gordon has sold roughly half his shares in the digital-giving company for around $12.4m.
Gordon - a former chairman of the company - was drafted in as CEO after the departure of co-founder Chris Heaslip in mid-2019.
It was the second sizeable insider sale recently, following anchor investor the Huljich family selling down its stake from 20.9 per cent to 15.7 per cent in a $124m block trade.
At the company's annual meeting in June, Gordon said he would step aside once a replacement was found.
Pushpay's first female director, Justine Smyth, had her appointment confirmed by shareholders at the same meeting, but resigned just weeks later on July 20.
An NZX statement gave no reason for Smyth's departure. In an email to the Herald, she said it was "a personal decision".
Pushpay shares were recently trading at $8.26, giving the Auckland-based software company a market cap of $2.3b.
Despite a recent dip, the stock is still up 166 per cent for the year, fuelled by a trend toward virtual church services during lockdowns - which in turn has driven demand for Pushpay's software for digital donations and congregation management.