Mr Drury sold 3 million shares in a placement to institutional and professional investors at $31.50 apiece in his biggest transaction since taking the company public in 2007.
He remains Xero's largest shareholder with 17.7 million shares, or about 13 per cent.
The transaction comes hot on the heels of Xero's first-half earnings announcement when it posted positive pre-tax earnings and unveiled plans to delist from the NZX in favour of a sole listing across the Tasman, which it says will encourage a broader range of analyst coverage and a wider pool of investors.
Mr Drury told BusinessDesk the sale was part of that strategy to improve liquidity in the stock with growing demand among global investors keen to back the company, which incorporates the move to a single-listing on the ASX.
"We've had global-grade investors wanting to invest in the company with really strong demand," Mr Drury said. We got advice on how to clear up our shares to allow their funds to come in - that's what we've put together."
He said the $31.50 per share sale was a "good price", with the stock closing at $33 on Thursday, having soared 89 per cent so far this year.
Mr Drury has watered down his stake in Xero before.
When it listed, he owned 45 per cent of the company with about 24.7 million shares, reducing that holding as the software company made headway around the world and attracted major institutional investors including big names such as Paypal co-founder Peter Thiel.
Mr Drury said the funds will lay the foundation for his future plans for philanthropic and social endeavours, although his family will be looking after that for now while he focuses on Xero.