The pay cut that paid off

Two respected industry figures, independently of one another, told Jason Ciccolallo the same thing: of the firms he was interviewing with, Orbis was the one that matched his personality. But, as those in the industry know, you often have to speculate to accumulate and for Ciccolallo, taking the job would mean taking a pay cut.

Betting that a values match would matter more than the salary, Ciccolallo took the pay cut. Eighteen years later, the bet has clearly paid off. He now describes it as the purest and most fulfilling stretch of his career. has clearly paid off.

What is Capital Conversations?

Each episode of Capital Conversations is an in-depth conversation with leaders of the financial industry. Host Steve Robertson talks to the people who have spent their careers raising capital and building client relationships across Australia’s wealth and asset management services. He digs into the decisions, the mentors and the mistakes that shaped how they do business today.

It’s also, occasionally, a small world. Robertson and Ciccolallo grew up just 500 metres from one another in Spring vale, in Melbourne’s southeast. Their paths never crossed as kids, but comparing notes on the podcast decades later, they discovered they had both been regulars at the very same fish and chip shop.

A career built on values

Ciccolallo’s career started almost by accident, in unit pricing at National Mutual in 1993, in the middle of a recession. Moves to HSBC, Merrill Lynch Investment Managers during the tech boom, and Fidelity followed.

At Merrill Lynch, still in his mid-20s, he found himself presenting balanced fund strategies to a client board with an average age of 60. He quickly realised he needed to know far more than he did if he wanted to earn their trust.

Each move after that, he says, took him somewhere a little more focused, a little more “pure.” Eventually, he found his way to Orbis and made the values alignment and pay-cut decision that would define the next chapter of his career.

For Robertson, that willingness to prioritise fit and values over the bigger pay packet is exactly why Ciccolallo is a great guest for the season two finale of the podcast.

“Jason had two mentors independently point him toward Orbis, even though it meant a pay cut, because they could see it matched who he actually was,” Robertson says. “The fact that he trusted that instinct, and has now spent 18 of his 35 years there doing what he calls the purest work of his career, is evidence of how deliberately he has approached his own path.”

Writing your identity down

One detail from the conversation that stuck with Robertson was a simple exercise Ciccolallo was set by his own boss.

“Jason talks about being sat down by his global CLO, who asked him what’s your legacy going to be, and what will your team be known for?” Robertson says. “He was given three minutes to write down the answer, and what came out of it was a strong client team identity, built around being competitive, energetic, resilient and reliable. It’s a simple exercise, but it’s clearly stuck with him ever since.”

Robertson also points to Ciccolallo’s philosophy on feedback and talent as central to his success as a leader.

“Jason talks about the difference between being nice and being kind, and how the kindest thing you can do for someone is give them honest, sometimes uncomfortable feedback,” he says. “What really comes through is how much energy he gets from putting people in situations that stretch them, watching them discover they’re capable of more than they thought. That’s a rare thing to be genuinely passionate about in this industry.”

“Jason is honest about the fact that this job means being told no, over and over again, so resilience matters,” Robertson says. “But he balances that with a real emphasis on individual accountability alongside collaboration, being adaptable and reliable as a teammate. It’s a thoughtful way of thinking about culture that a lot of leaders fail to actually put into words.”

What listeners should take away

For Robertson, the episode carries a message that applies well beyond funds management.

“Jason’s advice is simple: don’t try to be anybody else, be authentic,” Robertson says. “He talks about how clients can tell, over time, whether you’re being genuine with them, and that authenticity is ultimately what earns lasting trust.”

Capital Conversations, featuring Jason Ciccolallo, is available now on the Capital Outcomes website, Spotify and Apple Podcasts.