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Cloud, culture and continuous change

Santam’s migration to a cloud-based insurance platform marks a major milestone for the African insurance market. In conversation with Guidewire’s Leo Holesgrove, the discussion explored how cloud migration, AI integration and organisational culture are reshaping operational resilience, innovation and long-term competitiveness in insurance.
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Published on
May 25, 2026
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Technology conversations in insurance no longer happen in yearly cycles. By the time one catches up with an industry leader a few months later, the landscape has already shifted again.

Artificial intelligence dominates much of the conversation today, but behind the headlines sits another equally significant transformation taking place in insurance, the move from legacy, on-premise systems to cloud-native platforms.

In a recent discussion with Leo Holesgrove, Country Lead South Africa at Guidewire, we unpacked Santam’s landmark migration to the cloud, making it the first insurer in Africa to move its entire insurance platform to a cloud-based environment.  

“Things are moving so fast,” I remarked at the start of our discussion. “If you speak to somebody three or four months later, there’s always new stuff that has come up.” Leo agreed, laughing that “everybody’s on AI now,” but he quickly pointed out that major technology transformation is not something that happens overnight.

That became particularly relevant when discussing Santam’s migration project. “Implementation is not quick,” I noted. “How do you deal with rapid technological change when you’re busy with a long project?” He described the migration as “a marathon, not a sprint,” requiring deep planning, discipline and alignment between multiple stakeholders.  

He was quick to credit Santam’s leadership and internal teams for the success of the project. “The preparation they did and the attention to detail was outstanding,” he explained. “Without that, it wouldn’t have been the phenomenal success that it has been.”

At its core, the migration represents a shift away from traditional on-premise infrastructure toward a software-as-a-service operating model. But, according to Leo, this was about far more than modernising appearances. “It’s less about a new look and more about the fundamental reliability and speed of the insurance engine,” he said.  

For insurers, one of the major advantages is no longer being tied to physical hardware that depreciates and requires constant maintenance. Instead of lengthy upgrade cycles every few years, cloud platforms now receive continuous updates.

“Guidewire Cloud delivers automatic updates three times a year,” Holsgrove explained. “Clients stay on the latest version without disruption, and they can choose which capabilities they want to activate.” That continuous innovation cycle becomes increasingly important in a world where insurers are looking to integrate embedded AI, real-time data capabilities and intelligent automation directly into workflows.

Leo believes this fundamentally changes how employees interact with systems. “The intelligence assistant delivers answers, suggestions and actions directly in the flow of work,” he explained. “It effectively makes every employee an expert instantly because the information is always available.”  

Operational resilience also improves significantly in the cloud environment. Instead of depending on a single physical data centre, cloud architecture uses multiple availability zones to ensure continuity even if one location fails. From a client and broker perspective, the impact is equally significant. “Clients expect higher system uptime and fewer ‘system is down’ messages,” Leo said. “What this creates is insurance that just works.”

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Cloud migration used to be viewed as an innovation project. Now it’s becoming an operational necessity

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The move also enables faster claims processing through improved data handling and AI-driven assessment capabilities, regardless of whether the client interacts via a broker, call centre or mobile app. Of course, moving a large insurer to the cloud is vastly more complicated than simply switching systems. Insurance businesses often carry decades of legacy infrastructure, specialised products and deeply embedded processes running across multiple environments.

“You cannot just copy and paste old software into the cloud,” he emphasised. Instead, insurers need to re-architect integrations with downstream systems, refactor custom-built code accumulated over many years and, perhaps most critically, migrate massive amounts of sensitive customer data securely. “The data migration is what keeps most IT people awake at night,” he admitted.

According to Leo, the teams conducted numerous dry runs before going live to ensure there would be no data loss or operational disruption. Equally important, however, are the softer organisational elements that many technology projects underestimate. “The speed to travel depends very much on the internal culture of the company and the change journey,” he explained. This becomes particularly challenging because the business itself cannot stop operating while the migration takes place.

I asked Leo whether it feels like the goalposts constantly move during such projects, especially as insurers continue launching products, adapting to compliance changes and responding to competitive pressure during implementation.

“That natural tension is always there,” he acknowledged. He explained that projects often require “freeze periods” where certain system changes cannot occur, something that can frustrate business teams eager to move faster. “That’s where strong programme management becomes essential,” he said. “If you allow the goal line to keep moving, you risk an unsuccessful implementation.”  

When discussing why Guidewire has become such a dominant player globally, Leo highlighted the company’s deep specialisation in short-term insurance. Unlike broader cloud providers servicing multiple industries, Guidewire focuses specifically on the insurance market. “We understand the regulatory and actuarial complexities unique to this industry,” he said.

That specialisation is reinforced by substantial investment in research and development, with client feedback directly shaping future innovation priorities through Guidewire’s annual Connections conference. The broader question, however, is whether cloud migration is inevitable for the industry.

Leo believes the trend is unmistakable, although not necessarily identical for every insurer. “Cloud migration used to be viewed as an innovation project,” he said. “Now it’s becoming an operational necessity.” Legacy systems, he argued, increasingly struggle to support the real-time data requirements needed for generative AI, hyper-personalisation and modern digital insurance operations. “Large insurers cannot operate effectively without real-time data anymore,” he explained.

At the same time, he acknowledged that smaller insurers may still face barriers, particularly around migration costs, legacy complexity and regulatory requirements around data sovereignty in various African markets.

Still, for larger insurers seeking scale, innovation and long-term competitiveness, Leo believes the direction is clear. “We’re living in an always-on world,” he concluded.

“To compete in that environment, insurers need the scalability and sophistication that only cloud can provide. Santam’s move marks the beginning of that inevitability for the African continent.”

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