It makes it easy to forget that, like Weldon, he's also a Kiwi kid made good - with a heavyweight international career - who came home to take on the high-profile market-leading role.
Bennett grew up in the Wellington suburb of Karori, graduated with a degree at Victoria University and started his career in the local business world in the turbulent aftermath of the 1987 stock market crash.
That gave him good insight into some businesses with big problems: first with the National Provident Fund and then as the BNZ restructured after its government bailout.
In his early 20s Bennett took what he describes as "a big leap of faith" and continued his studies in the US.
He completed an MBA in strategy and finance at the Wharton School in Pennsylvania and embarked on a career in business consulting. Bennett was based in southeast Asia (Malaysia and Singapore) for nearly two decades, during which he was a partner at the firms Boston Consulting and Oliver Wyman.
One assumes it was for that, rather than his good sense of humour, that the NZX board hired him.
It is certainly with that consultant's outlook that he dived into, and restructured, the NZX business.
"When I took over this role there were a lot of surprises and we needed to do a lot reconfiguring of the business. And frankly that's what consultants do really well ... you spot what is wrong and fix it quite quickly and we did that. The second part about consulting is that it's a relationship business."
At the time, an enormous effort was being put into re-invigorating the financial markets, he says.
Change in the capital markets was being driven by regulatory reform, establishment of the Financial Markets Authority , the government assets sales programme and KiwiSaver.
"We had a big role to play in supporting all that." The business had some assets, particularly in the agri-business space, that didn't fit, Bennett says.
"So we embarked on a reconfiguration of the portfolio, which shifted our fund management revenue from next to nothing to 20 per cent of revenue." That's a part of the business that should grow 15-20 per cent at year, he says.
"We've got 43 different funds in our KiwiSaver, we've got 23 exchange traded funds. That supports the broader market." The business is much more focused on data and information. A good example of that is the new dairy derivatives, he says.
Bennett sees that as a good commercial opportunity bringing more sophisticated traders to the local market "but more importantly we need to provide risk management tools for the agri-sector".
However, the earnings performance of the NZX as a listed company in its own right - as opposed to the keeper of the wider market - has not been so flash under Bennett's tenure.
Shares in NZX the company have fallen since May 2012 when Bennett started, while the S&P/NZX 50 Index has more than doubled in value in the same period.
"The share price reflects the cost of dealing with a number of legacy issues including the Ralec litigation," Bennett says.
The Ralec, or Clear Grain Exchange litigation, has been a long-running battle which ended this month with no winner. Even the initial lawsuit pre-dates Bennett's start at the NZX and you get the sense that he found the whole thing, the purchase itself and the subsequent scrap, to be a frustrating distraction throughout his time.
He makes the case that the NZX is now a substantially different organisation to the one he inherited, with a different management team and business portfolio.
When I took over this role there were a lot of surprises.
It has also had no choice but to get on board with some historically significant regulatory reform in the past five years.
The size of the regulatory team has doubled.
"That said, the strength of our core business has been underlined by our ability to continue to pay our shareholders an attractive dividend," he says. "We now have a markets business capable of supporting the future growth of the capital markets and a highly-competitive, rapidly-growing funds services business, both of which we expect to deliver long-term returns to our shareholders for many years to come."
It must be a difficult juggling act, I suggest, balancing the internal business focus against the wider demands for the NZX to play a leadership role.
"In a lot of ways it's like being mayor of a small town," Bennett jokes. "The [public] role is overweight in terms of the size of the organisation. Having said that, exchanges play a critical role, we need to operate the business as an institution."
Bennett is adamant that both aspects of the exchange's role are crucial to its future.
"It's the dilemma people always talk about with an exchange, he says. "That it's a direct trade-off between, say, investing in regulation versus returning money to shareholders. But I don't think that's the case," he says.
"I've maintained from day one that you need to regulate well because you ensure confidence in the market." The NZX has also created a market development team and some of that also has a longer timeframe for payback, he says.
Bennett is philosophical about not being there to see the results of those long-term investments.
"I haven't got there yet but I said to Andrew Hamos [then-NZX chairman] when he hired me that five or six years is about the right time because inevitably your energy and commitment drops," he says. "I think you can look at some CEOs who have been around longer than that, in businesses like this, and you say, well they probably should have moved on and I don't want to be that guy."
So, what's next?
Bennett is heading to China with his wife, Sue, and adult daughter, Claudia, next month for a winter holiday in Yunnan province. "More of an experience than a holiday," he says. Beyond that he has no fixed plans and is looking forward, perhaps a little apprehensively, to the first proper break he has had for almost 20 years.
"What attracted me to the job here was the ability to contribute beyond the business, in the New Zealand context ... so something that matches my skill set ... we'll see what that is next year."
Bennett is passionate about the need for New Zealand to keep developing its small and mid-sized business and spread it wings in the tech sector.
As for the NZX, he agrees that it might be time for a different kind of chief executive, one with more local context than he had when he started.
"To be frank, I didn't have a lot of that context when I arrived. But that was a good thing ... so I could ask every question and turn every stone.
But we're not in that space any more, the business is in great shape, the direction is reasonably clear. I'm sure someone will tweak it but having that context will be important."