Simon Dougall on relationships, risk and the promise of insurance

This article forms part of CN&CO’s series covering The Insurance Conference Western Cape 2026. Across the series, we revisit the ideas, stories and conversations shared by the conference’s speakers, highlighting the insights that are shaping insurance, business and leadership in a changing world.

A formal invitation from the United Nations had arrived, but it did not make the visa process any easier.

Simon Dougall, CEO of specialist insurance brokerage Crawford Dougall, was preparing to travel to Geneva to speak about the Luxembourg Rail Protocol. Despite presenting his UN invitation, Simon’s South African passport earned him a Schengen visa valid for just three days.

It was a characteristically grounded moment in a conversation about something much bigger: the role insurance can play in unlocking rail investment and economic growth across Africa.

In discussion with CN&CO founder Carel Nolte at The Insurance Conference Western Cape 2026, Simon shared how a family business that began in KwaZulu-Natal in 1989 came to occupy an increasingly specialised place in hospitality, corporate, renewable energy and infrastructure insurance.

The answer, again and again, came back to relationships.

Understanding the client’s world

Crawford Dougall has worked with some clients for decades. Its approach is built on spending time inside their businesses, visiting their operations and understanding what keeps them awake at night.

From the outside, a broker’s visit to a remote hospitality property may look suspiciously like a family holiday. In reality, Simon explained, firsthand knowledge is essential to getting the insurance right.

“If we do not understand a client’s business, we cannot insure it properly,” he said. “And when that understanding is missing, everything further down the chain starts to falter.”

The importance of that promise had been brought home by a fatal aviation incident involving international tourists shortly before the conference. For the broker, the response extended far beyond processing paperwork. It included helping to bring those who had died to a central location and ultimately repatriating them.

It was a sobering reminder that insurance is not an abstract product. It is called upon at moments when something has gone terribly wrong and people need practical help, calm guidance and a promise to be honoured.

“You do not buy insurance because you have spare money lying around,” Simon said. “You buy it because, when the worst happens, you need to know that the cover will respond.”

Not every business risk can or should be transferred to an insurer. A good broker must distinguish between the risks a client needs to retain and those that can be insured, while continuing to push for better and more relevant solutions.

Putting African rail on the global agenda

Crawford Dougall entered the rail sector nearly a decade ago, initially working with a relatively small owner and operator of locomotives used across Africa. The opportunity was earned through years of specialist work rather than handed to the business on a silver platter.

That experience has placed Simon and his team near the centre of an important change in South Africa. As the national rail network opens to private operators, businesses will need to acquire and finance locomotives and rolling stock – assets that can cost between US$3 million and US$7 million each.

Those investments cannot happen without insurance.

“A bank is not going to lend millions of dollars against an asset unless there is a bankable insurance contract behind it,” Simon explained. “Insurance is not a footnote to development. It is one of the things that makes development possible.”

The Luxembourg Rail Protocol creates an international legal framework for recognising and protecting creditors’ rights across jurisdictions. It also provides for individual items of rolling stock to receive unique identifying numbers, much like vehicle identification numbers.

Over time, these digital records could allow insurers, financiers and operators to track an asset’s location, maintenance, service history and accidents across borders. Better information should support more informed underwriting and, eventually, more competitive pricing.

With South Africa and the Democratic Republic of Congo among the African countries to have ratified the protocol, Simon sees significant potential if it is adopted more widely.

“A stronger rail system could have benefits far beyond the railway itself,” he said. “Moving more freight by rail would reduce pressure on South Africa’s roads, improve logistics and create new opportunities across several industries.”

For Carel, an enthusiastically vocal supporter of South African talent, there was also pride in seeing a specialist brokerage from South Africa contribute to a global conversation at the UN.

Simon was quick to shift the focus away from himself.

“This is not really about Crawford Dougall,” he said. “It is an opportunity to represent our industry and help unlock something important for the country.”

Growing a family business

Crawford Dougall is a second-generation family business. Simon inherited a solid foundation but also faced the challenge of evolving the company without discarding the values on which it had been built. His approach has been to surround himself with capable, energetic people and give them the security and opportunity to grow.

“Whatever kind of business you are building, success comes down to people and the relationships between them,” he said.

Most people spend an enormous share of their waking lives at work, Simon observed, so it makes sense to do that work alongside people they like and trust. Build the right environment, enable people to develop and the appetite to succeed can do the rest.

That philosophy also shapes succession. Passing on a brokerage is not simply about finding the money to fund a transaction. It is about finding people who understand its relationships, protect its culture and can carry its promises forward.

Trust at the heart of the policy

Asked to explain what relationships mean in insurance, Simon’s answer was simple: everything.

“Policies change as risks, businesses and economies evolve,” he said. “What holds the arrangement together is trust – trust in how the broker presents a risk, how the insurer assesses it and how everyone responds when a claim occurs.”

For Simon, sport provides a useful parallel. A keen runner and triathlete from a sporting family, he starts his mornings with exercise to clear his head and maintain perspective.

Sport has also given him a drive to win, although he does not define winning as defeating someone else.

“It is the personal pressure to improve, learn and do better than yesterday,” he said.

That attitude fits insurance rather well. There is no final victory because risk never stops changing. New industries emerge, old assumptions fall away and clients continue to face circumstances nobody predicted.

The work, then, is to keep learning, keep improving and build relationships strong enough to respond when the promise of insurance is tested.