How a career of ‘calculated risks’ drove Zip Co CEO’s success

In a remarkable career spanning financial services, digital and telecommunications, Cynthia Scott has seized opportunities and embraced challenges

Zip Co Group CEO and MD Cynthia Scott’s career has seen her head up major multinational banks and embrace some big career pivots, including one that has seen her transform the once-struggling business into a stronger and more profitable consumer finance company.

It’s a “non-traditional, non-linear career” that highlights some of the most critical lessons Ms Scott says she has learned about the importance of taking calculated risks, recognising one’s value and surrounding oneself with great people.

In a recent AGSM Director’s Lunch conversation with AGSM Director and Dean of Lifelong Learning, Professor Nick Wailes, Ms Scott discussed her career trajectory and “whether people’s careers are strategic or planned, or whether they just end up unfolding”. Her career may exemplify how stepping outside one’s comfort zone and following opportunities can lead to extraordinary success.

“I will confess that my career unfolded rather than being strategic and planned,” she said, before discussing her education and career in brief, from getting her Bachelor of Commerce degree from UNSW Business School through to the executive and non-executive work she thrives at today. She attributed much of her success to having challenged herself continually and embraced unexpected opportunities; the rest, according to Ms Scott, is all about the people she has around her.

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“My strategy in work has always been to surround myself with brilliant people and bask in their reflected glory,” she said. “That’s kind of my flippant answer, but the truth is, for me to be able to develop and pursue the executive and non-executive careers that I have, I need a fantastic team around me.”

A career made by calculated risks

As an example of how her path has largely unfolded, rather than following a set plan, Ms Scott explained that even her decision to pursue a Bachelor of Commerce degree at UNSW Sydney, majoring in finance and Japanese studies, was slightly circuitous – she’d switched from her initial marketing program, and she landed on Commerce primarily to differ from her Arts-student sister. But the decision would help set the stage for everything that followed.

In her first role after university, at what is now UBS, she was offered a role at the bank and opted for the fixed-income dealing room, selling bonds and working alongside traders. “I absolutely loved it,” she said. “I loved financial markets; I loved the environment of the dealing desk. I loved just the volatility and the level of energy and activity.”

After six years, she moved to Merrill Lynch and transitioned to capital markets. This early experience with two large multinational banks in Australia was formative, she said. “One of the advantages of working in the Australian market is that you do end up being a bit of a generalist,” Ms Scott explained. “The fabulous thing about my early career at UBS and then Merrill Lynch was that I developed a broad range of skills in those two roles across a number of different aspects of finance, and I had that opportunity because I worked in big global businesses and multinationals, but I was in the Australian office.”

Next was a foray into domestic banks at Westpac, but a key move was in 2004 to Barclays, where the unfolding of her career picked up pace. “Barclays gave me incredible opportunities to develop my career, in part because I kept putting forward ideas, and they kept accepting them, which was great,” Ms Scott said.

One bold idea led her to Hong Kong, where she’d identified an opportunity for consolidating Barclays’ regional capital markets teams. While it was “rotten timing” personally, she said, this decision was one of those calculated risks that paid off for her and her family, not to mention her career.

After nearly four years in Hong Kong managing teams across five countries, Ms Scott returned to Sydney with Barclays as managing director of its investment bank and later as interim CEO and then CEO of Barclays ANZ. But at this point, despite these successes, she was eager for a new challenge, she said. “We’d gone from what was originally 12 people in Australia to about 175 at this point, the business was growing in profitability, and it was, by all measures, a great success,” she said. “But I’d been a banker at this point for about 20 years, and I felt very comfortable. And one thing you’ll gather about my career trajectory is that I’m not really comfortable being comfortable.”

New challenges and opportunities

Ms Scott next pursued executive education at Oxford and was awarded the Telstra Business Women’s Award for the private and corporate sector, two “thought-provoking” processes that prompted her to reflect on her career goals. “I wanted to take a step in my career that would really challenge me,” she said. She recalled telling her friends, “I want to wake up in the morning and think, ‘What the hell have I done?’”

So, stepping out of her comfort zone, Ms Scott joined Telstra as Head of Strategic Finance, where she managed an expansive portfolio that included group strategy, M&A and investor relations. Eventually, she would also oversee Telstra’s new and international businesses.

“It was a great way to move from being the CEO to not being the CEO, but also to move into an industry in which I didn’t have subject matter expertise,” she said. “Over the five years that I was at Telstra, I was blessed, frankly, to be given great opportunities to have responsibility for a variety of different companies, businesses and investments they had,” she said.

Next came a stint as Chief Strategy Officer and Business Development Officer at Scentre Group. Ms Scott then took a break with big plans to travel, but the timing coincided with the beginning of the COVID-19 pandemic; she ended up doing part-time consulting work instead.

“And then the Zip opportunity came along,” she said.

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Transforming Zip Co

Ms Scott was approached about the CEO role at Zip Co in November 2021, in an episode that again highlights the benefits of being open to new opportunities. “They’d been looking for a CEO for their Australia/New Zealand business – someone with payments expertise, and that’s not me,” she explained. “But we started a conversation about my background, my technical ability in managing capital, and my passion for managing people, and we realised there was quite a good fit in terms of what Zip was looking for and the skills I had.”

Zip had a very different strategy when Ms Scott started, operating in 14 countries with a focus on achieving high growth. When market conditions quickly changed, the impact on high-growth companies like Zip was significant and the company had to pivot its strategy accordingly. “I thought long and hard about my career and whether I was in the right place, and I got some great counsel,” she said. “I changed my mindset and decided that fate had put me here, and I did have experience and capability that were incredibly valuable to the company.”

Under her leadership, Zip has undergone a radical transformation, narrowing its focus to two markets – Australia/New Zealand and the US, delivering group profitability, achieving Cash EBTDA of $69 million for FY24 (an improvement of $117 million on FY23) and strengthening its balance sheet. 

“So, the transformation is going really well,” Ms Scott said. “But, importantly, I think more investors are beginning to understand the quality of business we’ve got, the value we provide our customers and merchants, and our ability to generate sustainable profitability.”

Career lessons and strategies

Reflecting on her appreciation for calculated risks, Ms Scott said the move from Barclays to Telstra nicely summed up her philosophy.

“I had people openly saying to me, ‘Why would you do that?’” she said. “And the answer was, if I had not made that move, I would not have got exposure to media, to telecommunications, to technology, to early-stage venture – to all these things that have been instrumental in what I’ve subsequently done. My counsel would be, if someone suggests that you should think about something, even if it feels random or risky or was not something you had thought about doing, absolutely take the time to determine whether it’s a calculated risk that you should take,” she added.

Another critical lesson Ms Scott promotes is reframing the concept of failure. The best advice she’s received as a leader was to “think about what ‘no’ actually means”, she said. It relates to how she ended up as interim CEO of Barclays at first – she’d initially declined the opportunity because she didn’t think she was the right candidate and was afraid to hear a ‘no’.

“If someone says no to you, it gives you an opportunity: it opens a door for you to ask the most valuable question in the world – ‘why?’”

It’s an “incredibly valuable way to get feedback”, she added, suggesting “reframing the word ‘no’ in such settings to: “What would you need to see from me that would give you the confidence to say yes?”

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Flexibility and building culture

Another essential aspect of Ms Scott’s leadership is a dedication to building a supportive work environment that allows employees to balance their personal and professional lives.

At Zip, she champions flexibility, believing it is vital for employee satisfaction and organisational success. “I’ve always done what was most important for the family first, and any company I’ve worked for would recognise that I’m very passionate about people,” she said. “And if you don’t have happy employees, and if they don’t have happy families, then you’re not going to get the best out of them.”

The majority of Zip’s US team works remotely, and in Australia and New Zealand, Zip has adopted a hybrid working model. “We think that we get access to the best pool of talent if we are more open to flexibility,” Ms Scott said. “But there is another side to remote working and having an entirely remote business: you need to make sure your managers have the skills to lead and manage a remote workforce.

“That’s not something that any of us were taught to do, and it is not the same as managing people who come into the office that you see four or five days a week,” she added.

Achieving the right organisational balance in this landscape involves building an inclusive culture that’s considerate of remote workers. Having a “higher bar” for manager training is also important, as is aligning the company’s performance structures and assessments, Ms Scott said.

“I’ll often say to people at Zip, ‘I have no doubt you can do your current job from anywhere; the question is, are you getting the skills and the development and the challenge to be able to do your next job? And we want your next job to be with us.’”