At the Steadfast Convention on the Gold Coast there was plenty of the usual bustle: brokers filling the marketplace, executives talking growth, sponsors talking opportunity and the industry performing its ritual of networking and self-examination. But hanging over the event was a larger issue: after three decades building and leading Steadfast, Robert Kelly is giving up the CEO role.
In the past, and to this day, successful leaders have strived to build durable systems around them and institutionalise what they do, whether it’s their business or their political movement. The Steadfast Group now has massive broking and underwriting networks that expand across Australia, New Zealand, Singapore, the US and the UK. In a few short years, this empire has grown rapidly.
As part of this empire building, Kelly took the disparate and separate individual firms that made up Australia’s insurance broking landscape in the early 1990s and brought them together into his network. In some ways this collaboration has given individual brokers more power.
“The radical part of the message was the idea that we would aggregate and collaborate and become a singular voice in the industry and try and drive change in a positive way, get a more democratic industry for all the small‑ to medium‑enterprise businesses in Australia who weren’t getting a fair shake from insurers, who were giving the fair shake to the loudest voices,” said Richard Crawford, CEO of Steadfast owned Community Broker Network (CBN).
But that collective power has arguably been wielded largely by Kelly himself.
When IB asked Kelly what he was leaving behind, he did not talk about a monument to personality. He talked about machinery. “This is just a platform and it’s a very sustainable platform,” he said, adding that it requires “great stewardship” and knowledge of “the intricacies of all the businesses.”
The man matters, but the system matters more. Kelly said the successor’s task is to “build on what we’ve built since 1996”, because “the job is not finished.”
“You rarely get a democracy that can disrupt or cause change to the extent that Steadfast has,” said Crawford.
Crawford’s broader point was that Steadfast’s next challenges are more structural: next-generation technology, systems, services and fulfilment across markets. The founder can hand over the baton because the business has moved from insurgency to maturity.
Steadfast's senators were making a strong succession case at their Convention.
“There is a whole team of really, really capable individuals running their own areas of Steadfast,” said Samantha Hollman, Steadfast’s CEO – International.
She added that Kelly had allowed CEOs across the three main platforms of the business to run those operations in preparation for this day. That sounds less like a court waiting nervously for a succession crisis than a managed transfer of authority inside an already functioning state.
Chris Longo, CEO of Novum Underwriting Partners, the firm’s relatively new acquisition in the US, offered perhaps the best imperial image of all: “His DNA is imprinted across the entire structure of the company,” he said. Longo added that everyone is “driving down the same road that he created.”
Outside the immediate executive management core, the Kelly tributes reinforced these points. Rick Wolozny, chair of Trident Insurance Group, called Kelly “an innovator” and “a thinker”, and said his legacy would “live on for a long time” because of the ideas, products and systems he initiated.
Steven Rudduck, CEO of HWS Specialty in the UK (acquired by Steadfast in 2024) said Kelly was a “driving factor” in getting a deal done and “truly is a legend in this marketplace”.
Kelly’s leadership has not been without controversy, and any serious assessment of Kelly’s legacy now has to reckon with that. In September 2024, the ABC’s Four Corners investigation into the strata sector questioned the transparency of Steadfast’s operations and its market influence, placing the group at the centre of a broader debate about conflicts of interest, disclosure and market power in strata.
Scrutiny sharpened again in late 2025. Steadfast told the ASX that Kelly had chosen to stand aside temporarily while an external investigation progressed into a workplace complaint made against him. The female COO who made the complaint was made redundant soon afterwards, according to a spokesperson, as part of a cost cutting exercise. The results of the investigation were not made public.
IB asked about the implications of regulatory and media scrutiny in terms of any governance concerns at Steadfast?
“I don't think we could tighten the business up any tighter than the way we operate,” said Kelly referring to the strata sector controversy. He said Steadfast operates scrupulously within the legislation and pointed to the past 15 months of engagement with the ACCC as evidence of that posture, saying the process had been constructive and had helped rebut what he characterised as false claims made publicly about the organisation. He added that Steadfast had been able to satisfy the regulator that it operates appropriately.
However, this could form part of the governance test that now surrounds Steadfast: whether a company built on scale, integration and influence can persuade the market, regulators and the wider public that its internal discipline is as strong as its commercial reach.
Kelly will remain on the board, the executive bench is deeper and the platforms are established. The governance language is stronger and the business, in Kelly’s own words, is “very sustainable.”
The coming test is not simply whether Steadfast’s republic can endure, but whether it can keep the confidence of brokers, regulators and the market while governing with enough imperial nerve.
Picture shows Steadfast executives Mark Senkevics, CEO Underwriting Agencies (left), Robert Kelly Group CEO (centre), Tim Mathieson CEO Australasia Broking (right)
