Sharesies, with its pink pineapple logo and fun approach to investing, has broken the mould in the conservative and clubby world of finance in New Zealand and Australia, appealing to a younger, less wealthy, but curious base of investors. 

It’s also broken with tradition by having not one chief executive but three – a triumvirate it calls Three Executive Officers (3EO).

The Wellington-based fintech start-up describes itself as a “wealth development platform”. 

It began with an easy-to-understand and low-cost equities investment method that offered fractional shares, making stock market trading fast and easy, and allowing ordinary people to take even tiny stakes in otherwise prohibitively expensive listed companies – especially big American stocks.

Accomplishment hailed

The three Sharesies musketeers – married couple Brooke and Leighton Roberts and Sonya Williams – have been shortlisted as finalists in the inaugural BusinessDesk CEO Index in the private company category. Our independent judges hailed what the three have accomplished.

“The Sharesies team has achieved a lot in a challenger role. They have a great ability to 3-CEO, which has been a new thing in NZ and has had good outcomes to date. They are breaking the mould,” the judges said. 

“They stood out as having the X-factor with that sort of leadership team. We rate them well on vision and impact, and on influence, they score really highly.”

Crypto addition

More than 880,000 NZ and Australian investors now buy and sell fractions of shares through Sharesies. However, the 3EOs say shares are just the gateway to an overall platform for investing and creating wealth. 

With $9 billion of platform assets, Sharesies investors have access to investing, saving, insurance, KiwiSaver, and crypto products. 

The crypto feature is just recent and was fuelled by customer demand. The new feature enables Sharesies users to purchase Bitcoin, Ethereum, XRP, and Solana through a partnership with the cryptocurrency exchange Kraken.

One aspect of Sharesies that some may not be familiar with is Sharesies Business, which collaborates with over 600 private and listed companies to understand better and connect them with their retail investors. 

The services include raising capital, staff share schemes, an investor relations tool, and a dashboard called Sharesies Open.

Whimsy typical

Why the pink pineapple logo? Sharesies describes the pineapple as the “crown jewel of the fruit world” and a long-term project in its own right, taking up to three years to mature. 

“It has a rich history of symbolism,” Sharesies says on its site. “In 17th- and 18th-century Europe, the pineapple became a status symbol of wealth, flaunted by the few who could afford such extravagance. But once in the hands of the masses, it told a new story of democracy.”

The whimsy about the pineapple is typical of the Sharesies approach to demystifying financial investment and having a little fun while doing it.

BusinessDesk asked Sonya Williams, Leighton Roberts and Brooke Roberts for their approach to the judges’ key criteria: vision, impact, innovation, resilience, and influence.

Vision: Sonya Williams says the three CEOs have always had a strong purpose to their ‘why’, and that is to create financial empowerment for everyone.

“We have a clear vision – which is to be at the heart of wealth for every person, family, and business.

“We try to be as transparent as we can about where we’re going,” adds Williams.

Senior leaders communicate the company's vision at every opportunity.

“I’d be surprised if there was a team member or stakeholder who didn’t know where we were going,” she says.

Having clear values and strategy supports a strong vision, she adds.

“Together we’ve found they determine your ‘how’, which really sets a clear culture across the business and gets us all rowing in the same direction.

“Over Slack, daily and weekly, team members celebrate others living our values, be it ‘chasing remarkable’, ‘in it together ’, or 'always care’. So everyone knows the values off by heart and they have meaning, instead of being something listed on the website and occasionally surfaced.”

The Wellington-based business, which also has offices in Auckland and Sydney, holds a full-day strategy session once a year. Twice a year, the leadership team conducts one-on-one meetings with everyone in the business to share its plans and gather feedback.

Impact: The three Sharesies CEOs assess their impact in various ways, placing the greatest importance on the value they bring to customers and on growing their team and culture.

Brooke Roberts says that with its B-Corporation certification – meaning it is part of an international scheme to benchmark companies that strive to do good – Sharesies can see the impact it has on its customers, its people, the community, and the environment.

The 3EOs get a lot from hearing anecdotes from customers on how their platform has changed lives for investors.

“We recently learned of a story about a sole-parent mum who joined Sharesies a few years back and grew her wealth to the point where she was able to finance starting up her own business,” says Roberts.

“That person had her vision and we were able to help in some way for her to move toward it,” she says.

Innovation: A key strength of Sharesies is breaking down very large problems into small pieces and executing at speed, every day, says Leighton Roberts.

“We have this strong view of the future we’re trying to create, which is financial empowerment for everyone, and this helps us identify the big hurdles we need to overcome to get there, and this motivates us to do the hard things along the way,” he says.

The leadership team encourages its people to focus on outcomes, opportunities, and customer pain points at all times, says Roberts.

“Innovation is something that comes out of understanding those problems really well and then solving them,” he says, though it’s never the focus at the outset.

Resilience: Leading a high-growth startup through its various stages over eight years has been both a challenge and a privilege, says Williams.  

“The rate of growth means it has probably felt like we’ve had eight different jobs, and eight different businesses across that time,” she says.

Factor in the expansion across various market environments and numerous global challenges, and the optimism of the Sharesies team has been key to navigating these, Williams says.

“Having co-CEOs helps us overcome challenges. Teamwork means we have each other’s backs and always feel well supported.”

Influence: Having influence isn’t something that Leighton Roberts thinks about often, but he says he is aware of it and grateful.

In terms of how he would like people to perceive his influence, the co-CEO says he would like people to understand that he has high expectations for Sharesies as a brand, a team, and for individuals generally.  

“I can imagine quite clearly what it would be like to have true financial empowerment in the hands of many, many more people and how that benefits people. That’s the genuine driver of our efforts.”

A good book (1): For Sonya Williams, it's The Psychology of Money by Morgan Housel. “We’ve always talked at Sharesies about the importance of understanding financial behaviours, and I think this book does a good job of unpacking that and underlining why it is so important,” she says.

A good book (2): For Brooke Roberts, it's The Most Human Human: What Talking with Computers Teaches Us about What It Means to be Alive by Brian Christian. “I love learning and diving into new topics, whether it be about a person who has tackled something hard to drive change, so I find myself mostly consuming non-fiction,” she says.

A good book (3): For Leighton Roberts, it's The Essays of Warren Buffett: Lessons for Corporate America. “His letters to shareholders and the insights of so many of his lessons are completely relevant today,” he says.

Sliding doors: Says Leighton Roberts: “I think for sure it would be finding a big problem to solve and finding a cool team to do it alongside – probably trying to get some sort of mass medical breakthrough. If I could swap a job and I had the skills, I’d probably be a doctor. That type of hands-on impact on people’s lives every day would be special.”

Brooke Roberts and Sonya Williams both say they already have their dream jobs.

Brooke Roberts, Leighton Roberts and Sonya Williams are finalists in the private company category of the inaugural BusinessDesk CEO Index. The category winner will be announced on Nov 18. BusinessDesk will publish a profile of the overall winner on Nov 19.

Read more of the BusinessDesk CEO Index here.