Auckland-based Vend - which makes software that allows cash registers to be replaced by iPads - has been sold to North American company Lightspeed for US$350 million ($455m).
Vend was founded in 2009 by Vaughan Fergusson, who had just sold his first startup - an online travel booking platform - to Trade Me.
Vend was valued at US$100m with its last major capital raise around 2016 - indicating the sale is a considerable payday for shareholders.
Ahead of the deal, the largest shareholder was local venture capital fund Movac with a 9 per cent stake.
Vaughan Fergusson, his ex-wife Mel Rowsell and early backer Sam Morgan were the next largest shareholders, each with an 8 per cent share (the sale represents Morgan's third major score after the trade-sale and his huge gains via his early Xero stake).
Milford Asset Management had a 5 per cent stake via its Active Growth Fund - a Kiwisaver vehicle.
And the sale will also represent major gains for two smaller earlier investors: Peter Thiel's Valar Ventures and Lance Wiggs' Punakaiki Fund.
Vend claims more than 25,000 retailers worldwide use its cloud-based point-of-sale software. It generated revenue of approximately US$34m in the 12-months to December 31, 2020, Lightspeed said in a statement.
The deal will close in April, subject to approvals.
The Canadian-founded, NYSE-listed Lightspeed is in the same market as Vend, selling cloud-based point-of-sale software, but is many times larger with a market cap of just under US$10b.
Vaughan Fergusson is today devoting most of his time to running the Pam Fergusson Charitable Trust, named after his paraplegic mother, who raised he and his two brothers solo.
Wiggs told the Herald, "We are delighted for Vaughan and his family, as well as the large number of investors and even larger number of people who participated in employee share schemes. It's a big day for all and we should celebrate this success."
Vend chief executive Ana Wight said her company had around 280 staff worldwide, including around 150 in its home base of Auckland.
Lightspeed was committed to the local office, and to expanding R&D - which could potentially see more staff employed in NZ.
Vend had at times been seen as an IPO candidate. Its trade-sale is another blow to the NZX.
It comes on top of today's news other big sale news - that Christchurch-based geoscience software maker Seequent has just been sold to Nasdaq-listed Bentley Systems in a US$900m deal, and Vocus Group's pending sale to Macquarie and Aware Super that has scuppered plans for an NZX listing of Vocus's NZ assets, valued around $722m.
The sale could also reignite debate over why so many Kiwi tech companies end up in US hands.
But Wiggs says such deals help fund the next generation of startups.
"I expect we will see a lot of these funds recycled back into the local tech community, as we will certainly do at Punakaiki Fund," he told the Herald.
Fergusson added, "When we started, there was essentially just Xero, and they weren't that big. Now there's this whole vibrant ecosystem of hundreds of [NZ tech] companies."
He would look to invest in startups, but also continue his mentorship role.
"I'm terrible at saying 'no' to people who ask for advice - but please don't print that," Ferguson said.