In that famous movie set in ancient Rome, Russell Crowe's Maximus was the general who became a slave who became a gladiator. In Australia's insurance industry, there's a different but perhaps equally compelling story of a technologist who became an insurtech founder who became a junior broker. Ben Webster (pictured) has reached commercial broking by an unusual route and like Maximus before him, the surprising thing about his third career was how little of what he knew still applied.
Webster spent more than 15 years building insurance technology, including travel insurance platforms selling through Finder and Compare the Market at a rate of 400,000 policies a year. He went on to co-found Agile Underwriting Services and recently started Pocket, a brokerage aimed at small businesses and founders. As part of that process, he enrolled to qualify as a broker himself. He holds a Tier 1 qualification and is working toward the full ticket while running the business.
"If I wanted to learn how to service brokers and build systems to help brokers on a day-to-day basis, I needed to do it at a really granular level," he said. What he found was a market that behaves nothing like the one he came from.
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Travel insurance is a commodity. A customer answers a short, standard set of questions, a price appears and the transaction closes. Webster said the experience was so frictionless that his own staff would redirect callers away from the phone, telling them it was faster to buy online. Commercial risk does not work that way and in his view it cannot be made to.
"And you can't compare a range of options for a customer in real time," Webster said.
The barrier is not technology it is that even in the same sector each business can be very different.
"So you can't go, I've got this risk, they're ANZSIC 6759, give me a quote," Webster said.
Insurers and underwriting agencies also classify occupations differently. Some use the Australian and New Zealand Standard Industrial Classification (ANZSIC) codes maintained by the Australian Bureau of Statistics. Others use their own schemes. A broker who wants to place one risk across six markets may have to map the same business six ways before a single question about the risk itself is asked and the question sets diverge from there.
Webster does not regard that as a failing.
"And that may be what the insurers see as their USP or their point of difference, that they ask different questions and that they map it differently," he said.
So the fragmentation brokers work around every day may be exactly what allows insurers to price and underwrite distinctively. The cost of that differentiation lands on the intermediary, in hours rather than dollars and it does not appear in anyone's expense ratio.
The consequence is that commercial broking remains, in Webster’s description, admin intensive in a way that surprised him. That sits against a market where most of the potential clients have done little preparatory work of their own.
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Vero’s 2026 SME Insurance Index, now in its fifteenth year and based on a survey of more than 1,500 Australian businesses, found that three quarters of small businesses have never completed a risk analysis, at 74%, while 43% reported a decline in revenue over the past 12 months. The index also found that four in ten businesses have no business continuity plan, and around one-third are not familiar with the term.
The scale of that segment is substantial. The Australian Bureau of Statistics counted 2,814,778 actively trading businesses at June 30 2026, and analysis by the Australian Small Business and Family Enterprise Ombudsman puts 98% of Australian businesses under the Australian Taxation Office’s $10 million turnover threshold for small business.
Most sit below the revenue line at which many brokerages begin to engage. Webster said brokers in the market commonly look for clients turning over $500,000 and up, and sometimes $5 million and up. Pocket’s position is to take the conversation earlier, before incorporation in some cases, when a founder is weighing a lease, a first employee and a contract review at the same time.
“I think we’re having earlier conversations,” Webster said. He described five conversations in a single week with businesses that had done a proof of concept and were considering incorporating, arriving with a version of the same request: I have no idea what I’m doing, can you help.
A client who has never completed a risk analysis cannot answer an insurer’s question set without being walked through it. That is the work the comparison screen for directly sold insurance aims to remove and it is the work Webster found waiting for him when he qualified.
Softening conditions make the arithmetic harder rather than easier. Pacific commercial insurance rates fell 12% in the third quarter of 2026, the eleventh consecutive quarterly decline, according to the Pacific figures in Marsh’s Global Insurance Market Index. Falling rates mean more remarketing, more submissions and more of the mapping work Webster describes, for less premium at the end of it.
Webster is not predicting that the problem gets solved. He described it as one with a source and a possible solution, before adding that the market is so far away from that it is not funny. In the meantime the work stays where it has always been, with a broker at a business asking the owner what it is they actually do.
