The nature of leadership was something Pushpay co-founder Chris Heaslip openly mused about as he took the digital-giving software company from a two-men-in-a-garage outfit to a $1 billion NZX-listed operation employing hundreds between its Auckland and Seattle offices.
Now the Kiwi entrepreneur has raised US$10 million ($14m) in a Series A round for his latest venture, Leadr, that addresses that very question with its cloud-based software for managing staff development and retention.
"What could you accomplish if every employee and volunteer at your organisation was engaged and growing as a leader?," Heaslip asks in a January 2021 launch video for his new company - which was formed in Seattle but recently relocated to Dallas.
Heaslip elaborated to the Herald this morning: "One of the biggest challenges I've faced starting and growing companies is developing leaders at every level of the organisation.
"I've found that healthy leaders build healthy teams, and unhealthy leaders build unhealthy teams.
"So a couple years ago, I started thinking about what it would look like to use technology to make people better leaders, and then in June of 2019, I called up Matt Tresidder [another US-based Kiwi] and we co-founded Leadr with a big mission to develop 1 million leaders through software."
Heaslip's pitch is that it's better to develop leaders inhouse - with the help of his software, naturally. He says he himself has hired in leaders from outside, during his career, but that the process can be slow and expensive - and there's no guarantee they'll be a good culture fit.
The US$10m round was led by New York venture capital firm Bedrock, which has around US$1b under management and is known as an early backer of startups including Lyft and Canva.
Heaslip also chipped in some of his own funds. And the raise was also supported by "Leadr friends and family" including Bobby Morrison - chief revenue officer at Xero's arch-rival in North America, Intuit - and Pushpay co-founder Eliot Crowther.
"Despite not having the New Zealand connection with engineering like Pushpay, we're still Kiwis innovating and taking on the world," Heaslip told the Herald this morning.
Although it's based in North Texas, two New Zealanders are central to the new venture. Heaslip himself as executive chairman and Leadr's co-founder and chief executive, Matt Tresidder.
"Matt was the fist sales rep at Pushpay and grew to lead the sales team," Heaslip says.
"At 27 years old, he was managing more than 100 people in his department."
Today, Leadr has 40 full-time staff and 5000 active monthly users of its staff-development software over 340 customers. Rapid growth should see its ARR (annualised revenue rate) will hit US$2m within a few months, Heaslip says.
Like Pushpay, which was initially wobbling on the ropes before the Huljich family came to the rescue with seed capital, Leadr was tested during its very early days.
"We were scheduled to launch last March and that was extremely difficult when Covid hit," Heaslip said.
"Most organisations were closed and certainly weren't looking to buy another tool. They were just looking to survive."
But once they came out of those first few months, organisations all had the same question. Heaslip said: How are we going to manage staff scattered to home offices under the new normal?
"So Leadr actually became a positive tool in helping organisations manage their staff remotely in a much better way." By July 2020, Leadr had 15 staff and things are starting to take off.
The US$10m will be used for more hiring, and the development of new core HR (human resource) and health plan modules.
An IPO is not yet on the horizon. There's a lot of fleshing out required before a public listing is even considered. "It's still early days. We'd like to build a full HR suite over time including payroll and HR and we have a lot of work to do to build those modules," Heaslip said.
Leadr's early customer announcements have featured churches. Is the young company concentrating on the same territory as Pushpay?
"We've found that the faith sector has really liked the product and the vast majority of our customers are churches," Heaslip said.
"But the product is a good fit for any business. Leadr helps organisations grow their staff, primarily through facilitating better one-to-one conversations and coaching - so you could see it could work for any organisation."