Deloitte Top 200: Chief executive of the year - Sky TV’s Sophie Moloney

“But that idea of enabling people to bring their whole selves to work, I think, is the key to unlocking amazing productivity.”

Last night, Moloney provided one of the best acceptance speeches in recent living memory of the Deloitte Top 200 awards, continuing that theme.

“It’s kind of exciting for media to be in the big end of town,” said Moloney, acknowledging fellow finalists, Fonterra’s Miles Hurrell and Xero’s Sukhinder Singh Cassidy.

Moloney said it was a privilege to lead Sky, and highlighted a recent Q&A with up-and-coming Warriors women.

“They had the opportunity to ask me any questions they wanted. This young woman said, ‘I have two questions for you’. It was quite serious. ‘Number one, do you classify your haircut as a mullet? And number two, does it say anything about your leadership style?’

“I thought, maybe there’s a future prime minister right in front of me with those great questions. I said to her, ‘Well, yeah, it’s a bit of a fancy mullet.’ I mean it’s not a cheap one... costs quite a lot to maintain. But it does show my zest for life. It is about saying you can be yourself, and we need everybody to be their most productive selves, if we’re going to see them thrive in Aotearoa and deliver on the promise of this country.”

It hasn’t all been plain sailing in 2025 for Moloney and her team, and the “be yourself” philosophy certainly came to the fore as the company faced a consumer and media barrage earlier in the year, with an ageing satellite, high up in space, causing all sorts of reception issues for customers on the ground.

Moloney relied upon her team to help lift Sky off the canvas.

“That was phenomenal teamwork, discretionary effort that money can’t buy. You know, you don’t go into media if you necessarily want to drive the most revenue in your career. You do it because you love it, and the level of discretionary effort we secured over that time and delivered on has made us match fit.”

Operationally and strategically, and with the satellite issues now in the rear-view mirror, Sky has had an enormous second half of 2025.

In July, Moloney announced the $1 acquisition of Three and Three Now from Warner Bros Discovery - finally giving Sky TV fully fledged, free-to-air linear and digital platforms, opening new audience and advertising revenue opportunities.

In August, the company announced it had snared New Zealand rugby rights for another five years, on vastly more sustainable terms than the existing five-year deal, which was signed in 2019.

Spark Sport had been in the market in 2019 and a week before the rugby rights announcement, it had announced it had secured cricket rights over Sky (as well as already having a suite of international sports deals).

Sky reportedly agreed to pay around $500 million for the five-year rugby rights; the new deal has been reported to be around $85m a year, which would equate to a total $425m.

Moloney is a big fan of American business author Patrick Lencioni and a people-first philosophy.

“One of the biggest leadership learnings over time is about how do you make sure you not only have the best team, but that you’re also doing the best job to support them?” she says.

“When I had the opportunity - and awesome privilege - to lead Sky, we were in the fight of our lives. It was pretty rapid decision-making.

“Back when chairman Philip Bowman took over, there was a $100 million bond to repay and a capital raise that we went through.

“Spark Sport was in the ascendancy - a much, much bigger company than us. Spark was in the market - we had a significant rugby deal done back in 2019. It was super important to secure those rights. We were absolutely going for it. When you step in at that stage, it’s quite rapid-fire decision-making.

“Then Covid hit, which no one expected.”

Moloney, who joined Sky in 2018 as general counsel (later chief legal officer) before becoming the chief commercial officer, and then chief executive in December 2020, says she has learned over the past five years that good things take time - “knowing when to be patient and knowing when to be a bit impatient and when you need to go for it.

“That’s about experience and judgment and listening and having great counsel from the chair of the board, and my team ... and at home.

“We call our exec team a home team with real intention, because I don’t want anyone coming here and not giving it their all. When you’re at home, you tend to see your best and worst behaviours. Don’t come to work to be a dickhead, but bring your full self to work - that’s absolutely what we’re about. So we talk about the exec team being the home team - their natural self ... be yourself.”

Moloney commutes to Auckland every week from Nelson, usually flying north on Sunday and back to the Mainland on Thursday evening, so that she can work from home on Fridays. It’s been her same routine since joining Sky.

Moloney lives in Tāhunanui with her husband William and twin sons, who have just turned 17. An older son has left home and is now at university.

“I like to talk about the fact that we’re business athletes and we have to keep ourselves fit and well,” she says of her and her team.

“So my weekends, as the team know, are pretty sacrosanct for me in terms of getting down to Nelson and seeing my boys, my husband and our dog, and going for a walk and decompressing. The key thing is getting there and being present; you can be physically there, but not mentally, but I’ve got pretty good at separating that.

“It does mean that I don’t get to as many events and things as perhaps some of my colleagues might like, but equally it’s really important to help make sure that I can be the best version of myself at work.”

Around the executive table, and with her staff, Moloney believes she has got a lot better at “being present, and listening, and asking that next question which I think as a leader is vitally important.

“You should be asking more questions than giving answers. And also getting better at knowing when, actually, it is time to make a captain’s call. It’s great to collaborate, but once you’ve got information, you can see there’s a path and you’re prepared to make the call.”

With a background as a commercial lawyer, Moloney has been both general counsel and chief commercial officer for Sky. “I didn’t want to just advise the decision; I wanted to be able to take the decision. It was a shift after being in legal for a decent period of time, but I worked it out that I was starting to get frustrated ... ‘Come on!’” she laughs.

One of her big focuses now is fully integrating Three Now and Three into the Sky environment. “We have a big project to disentangle from Warner Bros Discovery, but the opportunity of that combined set of assets and the combined audience is hugely exciting.”

She says both companies are 35 years old and have been through some uncomfortable periods, seeking financial stability. In that sense, there were a lot of cultural similarities. “It’s kind of a new Sky, if you like, with the two businesses in one.”

The acquisition of Three and Three Now was also a “game-changer” in helping Sky acquire the rights for the Summer and Winter Olympics through to 2032. The free-to-air channels open up stronger revenue opportunities for the business.

Sky won the Olympics rights but missed out on next year’s Football World Cup to TVNZ, which is introducing its own screen subscription strategy.

“We’ll always put forward the best bids that we can, but we also know we can’t have all rights,” says Moloney. “We’re really clear about where we can drive returns, and we’re really comfortable that - if we’re not successful - we put our best foot forward.”

She’s also excited about identifying new audience opportunities for Sky, understanding New Zealand’s changing demographics and “how we make sure that we can deliver to the entire country but also drive a sustainable margin from that business”.

The company had also reviewed the launch of its new Sky Experience - a new Sky Box and Sky Pod - which have had teething issues over the past two years.

Moloney has learned from that experience, including only going to market with a date once full testing has been undertaken. “The good news is that the product is super performing and 4K UHD is coming - you can only get it on the new Sky Box. Even though it was a tough start, it was the right strategy.”

Moloney welcomes the “competitive tension” within the media industry.

“When you look around the world, you want entities that care about this place. That’s us. That’s TVNZ. We’re not talking about big offshore revenue opportunities. We’re talking about telling stories here and caring about audiences here. It’s really important - including for the NZ Herald and Stuff - that we have this journalism and creative storytelling. It’s super important we don’t lose that.”

Sky TV’s share price has climbed past $3.50 in recent weeks into five-year highs for the pay-TV operator.

There have been rumours in the market of a potential new owner. Private equity eyes have never been far off Sky TV. In October 2023, Sky revealed it had received “a highly conditional, non-binding preliminary expression of interest from a third party to acquire all of the shares in Sky”.

But it said at the time that the proposed transaction “falls short of the board’s view of the fair intrinsic value of Sky and, based on recent unsolicited feedback, the view of a number of Sky’s institutional shareholders. The board has advised the third party accordingly, and has ended discussions in respect of the non-binding indicative offer.”

Forsyth Barr analyst Ben Crozier recently cited Sky’s dividend of at least 30c per share, coupled with the tailwinds of the successful rugby rights negotiations and the Three acquisition, as big factors in investor interest.

“If you look at the Discovery deal that they signed – near term it will be a small positive free cash flow, but they are expecting that to grow, and we are too, to $10 million or so free cash flow impact,” he told the Herald in October.

“Market is backing management – Sophie and the team have done a good job over the last few years in executing cost out. The market is looking ahead and backing them to be able to deliver.”

Moloney has been working with an executive coach recently on what drives her. She certainly sees huge opportunities in front of her at Sky TV, ensuring she delivers for shareholders on the Three acquisition and other strategies.

“I grew up on the sidelines of rugby fields and cricket pitches, my dad being a headmaster. He used to direct plays and I used to be there in musicals. When I look back at those formative childhood years, there’s a lot of sport and entertainment. So I love what we do.

“There’s a huge opportunity in front of us. But equally, being a subscriber to Good to Great, the Jim Collins book, succession planning shouldn’t be a big moment for the company. So that’s something that I will definitely be working on with the board.

“Of course, that’s the chair of the board’s purview, but that’s not anytime soon. There’s a lot more to do.”

As the boss of our biggest company - a co-operative with more than 8200 farmers - Fonterra chief executive Miles Hurrell is never short of hearing a good opinion.

“Part of the attraction [of the role] is there’s no smoke and mirrors when it comes to farmers,” says Hurrell, who is once again a finalist for chief executive of the year in the Deloitte Top 200 awards. He won the award last year.

Judges say this year’s nomination is partly based on the way Hurrell has used his humility to help restore trust in the co-op from its farmer owners, and deliver an “extraordinary” performance.

“They tell you exactly what it is [that is on their minds],” says Hurrell. “Making sure you never lose sight of that is important; now it takes a bit of resilience at the same time.”

Hurrell - who has been at the firm for 25 years, the last seven as chief executive - also has some long-time colleagues who know exactly when he arrives at work each day, and have no qualms about an early morning natter to put the world to rights. He doesn’t mind that either.

Having come up through the ranks, he knows the importance of company-wide communication.

“I’m getting a bit longer in the tooth now, but I feel it wasn’t that long ago I was an employee ... with three or four or five levels between me and the chief executive.

“Knowing what it was like in some of those roles where you didn’t have clarity but decisions were made … I’m conscious of that. I think about it quite a bit.

“There are some things you can’t share for obvious reasons, but how do you give enough information that gives people the confidence that we’re heading in the right direction?”

Hurrell has had another familiar figure to deal with in recent times, NZ First leader Winston Peters, who was a trenchant critic of Fonterra’s plans to sell its consumer business - including iconic brands such as Anchor and Mainland - for nearly $4 billion to French dairy giant Lactalis.

The sale has been confirmed, with some 88% per cent of farmers voting in support - it means a substantial payout for them, but Hurrell says they are all keenly aware of the future and the need for Fonterra to reinvest its own return.

“Despite some people in the media talking about selling the future for the short-term sugar hit, all the questions from farmers have been, ‘What does the long-term future look like?’, ‘Where do you reinvest?’

“We’re pivoting as an organisation, focusing very much on our B2B business. The farmers want to know about that - not ‘When’s the cash coming?’, ‘How much is it going to be?’

“To see the support of 88% is great because it gives us, I think, the mandate to go forward and deliver upon the new strategy that we set ourselves. It is exciting.”

Deloitte judges noted Fonterra’s strong financial performance in FY25, delivering a $1.7 billion operating profit, up from $1.5b in the previous 12 months.

It also delivered a record price to farmers of $10.16 per kilo of milk solids in the 2024/25 season, with a forecast range between $9-$11 for the 2025/26 season.

Judges also highlighted Hurrell’s work in leading a business that was now assessing a pipeline of potential growth investments, with plans to invest up to $1b over the next three to four years in value-generating projects and operational cost efficiencies.

Are awards like the chief executive of the year title important for Hurrell?

“For the company,” he says. “It’s not what gets me out of bed in the morning, but to see the organisation recognised, again, from where we’ve come from.

“I think we’ve got to put it in the context of where we’ve come from, not just as an organisation, but as an industry as a whole. When I talk to farmers, they still feel a bit bruised around [not being recognised for] the role they play in the New Zealand economy and those sorts of things.

“And so to see it recognised - that for me is quite important. Overlay that with the economic situation that New Zealand finds itself in, and farmers are doing their fair share of heavy lifting. All these things go some way to recognising the role they play.”

Hurrell believes the majority of Kiwis do understand and appreciate the role of farmers, and have done so for decades. But there were still a noisy few “that sort of dragged that down in the past”.

He believes the positive sentiment now outweighs the negative.

What does get him out of bed then?

“Well, firstly, a 12-year-old son. Getting him motivated and off to school is probably the first thing that gets me out of bed,” he laughs.

“But I think it comes back to knowing why we exist as an organisation. Effectively, being a cooperative, we are just a collection of small companies. I’m heading up a whole lot of small companies, if you like, that are successful in their own right in terms of farming businesses.

“So to recognise the role we play to support them, and we’re really just an extension of their business.

“Anything we can do to support them - whether it be through economic support or other things - that’s the bit that drives me.”

Sukhinder Singh Cassidy is dialling in from Sydney. She is a Canadian who lives in San Francisco, running a business with firm and proud roots in New Zealand.

Singh Cassidy is living proof of how Xero’s technology tentacles have spread around the globe, ever since the small business software firm was founded in Wellington (and where it is officially still headquartered) by Rod Drury and Hamish Edwards almost 20 years ago.

For Singh Cassidy - one of the three finalists for this year’s Deloitte Top 200 chief executive of the year award - her Silicon Valley base gives her convenient access to Xero’s expanding world.

“The good news is I actually live in a very friendly time zone for all that travel. If you wanted to run a global portfolio that went from Australia to the UK, it turns out that the US is dead-set in the middle of those two time zones.

“I think it could be that San Francisco might be the one place you can get a direct flight to anywhere, and I’m only half joking when I say that.

“It actually works quite well because I wake up in the mornings and I have a couple of hours on email. I know exactly when I can get the US and UK in the morning. I can get Australia and New Zealand in the afternoon and evening.

“It works quite well and it’s very similar to the rhythm I had at Google.”

Singh Cassidy has been the chief executive of Xero for just over three years and has been recognised by the Deloitte judges for her transparency and alignment for investors, employees and customers. Her leadership focus, say judges, centres on maintaining consistency between the company’s stated strategies and actual actions.

“She prioritises executing Xero’s ‘three by three’ strategy, evolving from volume to value-based selling, championing AI and innovation throughout the company and fostering a diverse, globally distributed leadership team,” say the judges.

Xero’s “three by three” strategy focuses on building solutions for three critical small business functions (accounting, payments and payroll) within three primary markets (US, UK and Australia).

The judges also said: “Sukhinder empowers employees to leverage AI for productivity and ensuring that the organisation remains focused, congruent and strategically aligned during growth and transformation.”

They specifically noted Xero’s recent ‘AI Explore Day’ in which 4500 employees were trained on AI tools.

Singh Cassidy is speaking to the Herald on a call from Sydney, the day after announcing ASX-listed Xero’s half-year results - a 42% jump in net profit to a record $135 million for the six months to September 30.

Despite the result outpacing analysts’ predictions, she has a short-term challenge of helping restore Xero’s share price - in the days following the half-year result announcement, it had fallen below $A120, from around $A140.

Much of this drop has been attributed to investor scepticism about Xero’s A$2.5b ($4.1b) acquisition of American payment firm Melio.

Singh Cassidy told journalists that she tried to avoid looking at the share price, but rather focused on what consistently creates value. “That’s about the only important thing we care about. How do we make sure we’re delivering consistent shareholder value?”

She tells the Herald she’s at Xero for the long haul.

“We have a lot we want to accomplish ... our aspirations are quite large. We just acquired Melio, and we set the aspiration to more than double the business (based on Xero’s annual revenue) from FY25 to FY28.”

Inside of that, Xero needed to set itself as an “indispensable, AI-driven platform for our customers”.

“We need to drive the purpose and productivity of Xero using tools like technology. We have a lot of big markets we play in - Australia, the UK, the US - and they all have different needs.”

Singh Cassidy has a storied CV, peppered with time on boards, in the C-suite and as a start-up founder. She spent six years at Google, as president of Asia, Pacific and Latin America operations. She has been a director of Ericsson, Urban Outfitters and TripAdvisor and President of StubHub. She has also had work stints at Amazon, Sky UK and Merrill Lynch.

She took time to identify her present role, ensuring that she found a company that aligned with her own values, including its inclusiveness and approach to innovation.

“I was looking for my next CEO job, and it had been a very long search. I was a little discouraged that I hadn’t seen anything that inspiring, and then Xero called.

“I arrived at a company that is very in sync with my personal values ... it’s very diverse, it is very global in its thinking. I think that comes from New Zealand [roots]. I’m Canadian, so I resonate a lot - when you’re born of a small market, you’re always outward-facing.”

She also knew the Xero product, having been a customer through her own small business.

“I just have a lot of empathy for our customer and what they’re trying to do in the world - as a daughter of a small business owner, as a small business owner myself, as a user of the product. And then also recognition that our customers are more than small businesses - they’re also people, and consumers of technology. They want it to be easy, they want it to give them value. I have an affinity.”

Like the other two finalists in this year’s chief executive of the year award, Singh Cassidy’s family life gives her an important balance to a hectic workload.

“I’m either on or I’m off. On the weekends, I like to be unscheduled. I have three children and, like any proud parent, I spend the time that I am not working [where] I want to go watch their sports. My daughter plays water polo, and my son plays basketball. That gives me a ton of joy.

“I’m a big tennis fan myself, so I play a lot of tennis.”

But she also adds that work gives her an important purpose.

“As long as my family is healthy ... you get to wake up and go to work and it’s tactful with great people. That work needs to be purposeful and it needs to be addictive and I don’t think of work as outside of my purpose. It’s an inherent part of my purpose.”

The Chief Executive of the Year Award is sponsored by ServiceNow.

Editor-at-Large Shayne Currie is one of NZ’s most experienced senior journalists and media leaders. He has held executive and senior editorial roles at NZME including Managing Editor, NZ Herald Editor and Herald on Sunday Editor and has a small shareholding in NZME.