Standout debut for The Insurance Conference Western Cape

The 2026 Insurance Conference Western Cape – the first of what promises to become a standout fixture on the insurance industry calendar – took place at Plaisir Wine Estate near Paarl on 20 August, followed by a programme of partner activations the next day. It was an intimate yet far-reaching affair, welcoming around 250 guests in person and a further 3 000 online.

The format was refreshingly different from that of a traditional conference. Presentations were short and sharp, while the content was relevant to the insurance industry without becoming overly technical – ensuring there was something for everyone.

What truly set the conference apart was its atmosphere. The event unfolded seamlessly: conversation flowed, wine flowed and music filled the venue.

CONFERENCE DAY

The format was modular. Guests got to choose which parts of the event they wished to participate in: the business sessions, the evening’s “smul” dinner – informal, casual, relaxed – or the partner activations from iTOO, Camargue, Fulcrum and Lombard.

Sponsors welcomed guests to their stands in the glorious winter sunshine before the official proceedings began.

The presentation session was MCd by CN&CO founder Carel Nolte and Executive Head of Elite Risk Underwriters Tandiwe Cimela.

Accomplished classical and jazz pianist, Charl du Plessis, was first at the rostrum (or rather, the baby grand). Charl drew parallels between musical performance and insurance, showing that technical expertise had to be balanced with creativity, adaptability, empathy and careful listening.

Through live musical demonstrations, he explained how professionals could interpret the same underlying “score” in different ways – and how strong leadership created space for others, responded thoughtfully to unexpected circumstances and transformed even a small contribution into something meaningful.

“Leadership is not about playing louder; it is about creating the conditions in which somebody else can be heard.” – Charl du Plessis

Up next was Kate Weaver Gibbs, CEO of Are You OK?, who explored why empathy is essential throughout the insurance value chain – from policyholders and brokers to underwriters, claims professionals and leaders. She explained that empathy does not mean abandoning processes, boundaries or commercial discipline, but choosing to understand the human context before responding.

By treating insurance as a human chain rather than a mechanical transaction, organisations can support their employees, build trust with clients and create stronger, more enduring relationships.

Kate’s talk was sponsored by Global Choices, in line with its commitment to the practice of empathy as a key component of the insurance value chain.

“We might see a claim number, but the policyholder sees an entire life – and that is the distinction that matters.” – Kate Weaver Gibbs

Rianet Whitehead, founder of The Insurance Apprentice, then spoke with the programme’s top three apprentices for 2026 – Karabo Mashego, Asanda Magwaza and Tyrell Moodley – about whether the insurance industry was prepared for its future customers, risks and workforce.

The apprentices argued that insurance needs to become simpler, more personalised, proactive and accessible, particularly for customers who find short-term products difficult to understand. The discussion highlighted the need for insurers to respond faster to emerging risks, redesign products for underserved markets, offer practical risk-management support before claims occurred and distinguish genuine innovation from merely digitising outdated processes.

The apprentices also believe that young professionals should be encouraged to question established practices, collaborate across traditional roles and help shape an industry that retains trust and human connection while adapting to technological change.

“If you went back to the drawing board and designed the product today, would you design it the same way?” – Karabo Mashego

“We need to communicate insurance in a way that people can understand – if they do not understand what is being protected, they will not value it.” – Asanda Magwaza

“Short-term insurance is not a solved problem; every new innovation creates an entirely new product category and new opportunities.” – Tyrell Moodley

Justin Naylor, CEO of iTOO, challenged the perception that insurance is dull or conventional, arguing that it is an essential force behind innovation and human progress.

Using examples ranging from unusual celebrity policies – Dolly Parton’s breasts and Bruce Sprinsteen’s voice – and the earliest motor insurance, to satellites, renewable energy, cyber threats, artificial intelligence and autonomous vehicles, he showed how the industry gives entrepreneurs and investors the confidence to pursue ambitious ideas.

Justin believes insurers have a responsibility to anticipate emerging risks, collaborate across the global insurance ecosystem and create solutions that unlock the potential of businesses, individuals and the African continent.

“Every leap forward in human progress requires someone to insure it first.” – Justin Naylor

Paul Griessel, CEO of Aon Re South Africa, helped to demystify reinsurance somewhat, explaining how the sector has evolved during his four decades in the industry. He described reinsurance brokers as strategic partners who combine global capital, analytics, modelling and market insight to help insurers manage volatility, protect their balance sheets and pursue growth.

Drawing on events such as the 2021 KwaZulu-Natal floods, he highlighted the crucial role that reinsurance plays behind the scenes in sustaining insurers through major losses.

While technology has transformed the industry, he maintains that trust, personal relationships and close collaboration remain fundamental to its success.

“When capital, clarity and confidence come together, organisations make better decisions, build stronger partnerships and create more resilient businesses.” – Paul Griessel

In conversation with Carel, Simon Dougall, CEO of Crawford Dougall, explained how the family business has grown from its KwaZulu-Natal roots into a specialist brokerage serving sectors such as hospitality, aviation and rail.

Simon pointed out that effective broking begins with understanding a client’s operations, risks and concerns so that the promise of insurance holds when something goes wrong.

Discussing South Africa’s rail reform and the Luxembourg Rail Protocol, he highlighted how stronger creditor protection, improved asset data and appropriate insurance can attract investment and enable economic growth.

Throughout the conversation, he identified people, trust and enduring relationships as the foundations of both Crawford Dougall’s success and the wider insurance industry.

“Insurance is not a footnote; it is an integral part of enabling growth and development.” – Simon Dougall

In conversation with Carel and Tandiwe, Denise Walker, COO of Caby, shared how extensive research and persistence underpin the development of the locally built e-hailing platform.

Caby aims to offer drivers a fairer share of ride income than other e-hailing services, while improving safety through rider and driver identification, journey tracking, emergency alerts and restrictions in high-risk areas.

Denise also discussed the setbacks she encountered during the company’s seven-year development phase, the importance of securing an investor who believes in the concept, and her determination to build a business that responds to the realities facing South African drivers and passengers.

“We are a local team, and nothing goes out of the country – it is about ensuring that drivers receive a fairer share.” – Denise Walker

Dr Ronel Retief, registrar at the University of Stellenbosch, explored what leadership requires when nobody knows what will happen next. Drawing parallels between higher education and insurance, she explained that both sectors make long-term promises in a rapidly changing world and must navigate complex problems for which no proven solution exists.

She encouraged leaders to replace false certainty with adaptive action: observe what is happening, consider what it means and take the next wise step. Through examples from the pandemic, severe weather and a major university system implementation, she identified collaboration, compassion, authenticity, honesty and experimentation as essential leadership practices.

She also stressed that leaders must communicate openly, acknowledge uncertainty and create space for recovery in ways that work for each individual.

You can download the full copy of Ronel’s speech here. It was truly inspiring!

“Perhaps leadership today is not the provision of certainty; perhaps it is helping people to act well without it.” – Dr Ronel Retief

Susie Goodman, executive director of Strauss & Co. Auctioneers, offered a lively look at the opportunities and risks within the African art market. She explained how the auction house connects African art with buyers worldwide while promoting overlooked artists, educating new audiences and keeping important works on the continent.

Through stories involving valuable artworks, forgeries, theft, transportation and unexpected discoveries, she demonstrated why specialist insurance and trusted partnerships are essential to the business.

Her account of a previously uninsured Pierneef painting – found beneath a bed and later sold for R21 million – illustrated how identifying and protecting an artwork’s value can transform a family’s future.

“The art world is an amazing place. It is fun, dynamic, challenging and sometimes scary, but we certainly could not do it without insurance.” – Susie Goodman

Clark Gardner, Chief Executive Officer of the Sanlam Cape Town Marathon, recounted the event’s demanding journey towards becoming Africa’s first Abbott World Marathon Major. He credited its progress to strong partnerships, a shared purpose and a willingness to learn from repeated setbacks. After the 2025 race was cancelled because severe winds made the route unsafe, the team responded with transparent communication, partner support and a determined seven-month recovery effort. By attracting international runners and elite athletes while retaining an authentically African character, the marathon advanced its broader purpose of stimulating tourism, creating employment and showcasing the continent to the world.

“When things go wrong, we can overcome them. It is not the end of the world.” – Clark Gardner

Conference day ended with a sensational entertainment line-up and a casual, conversation-inspiring dinner filled with “smul” delights, with guests interacting and engaging late into the night.

PARTNER DAY

Kicking off Partner Day was a 10 km fun run/walk – or slightly shorter in some instances – hosted by iTOO.

Later, guests enjoyed two fascinating and delicious wine-centred events, sponsored respectively by Camargue and Lombard.

The day’s activities also included a lively and exciting padel tournament hosted by Fulcrum.

“Partner Day was especially popular with guests, who embraced every opportunity to connect, unwind and enjoy the activities together,” says Carel. “Overall, The Insurance Conference provided our partners and exhibitors with a unique opportunity to network with a select group of delegates representing the cream of the insurance industry.

“The feedback has been exceptionally positive, and we can’t wait to host The Insurance Conference Western Cape again in 2027.”