Sara Winstone, managing director at Lightstone, has witnessed the property industry’s transformation from information scarcity to a data-rich, increasingly intelligence-led market.
Source: Supplied. Sara Winstone, managing director at Lightstone.
In this Women’s Month Q&A, she explores how technology, data and artificial intelligence are reshaping property — and why the biggest opportunity lies not simply in adopting new tools, but in using them to build a more connected, transparent and trusted ecosystem.
Winstone also highlights the growing influence of women in the property market, arguing that they should play a greater role in designing and leading the technologies that serve it. From leadership and innovation to the future of PropTech, she shares her perspective on what lies ahead.
You’ve seen the property industry evolve significantly through technology and data. What do you believe has been the most transformative change in PropTech during your career, and what does it mean for the way property businesses are led today?
I don’t think the biggest change has actually been technology. It has been the democratisation of information, and, as a result, a fundamental shift in where trust sits in the property market.
Twenty years ago, there was a huge information imbalance. Buyers relied on agents for market knowledge, sellers often relied on anecdotal views of what their homes were worth, and lenders relied heavily on manual valuations and individual professional judgement. Today, almost everyone in the ecosystem has access to far richer information. That has changed not only how decisions are made, but what customers expect.
When Lightstone introduced South Africa’s first Automated Valuation Model (AVM) with Absa in 2006, automated valuations were largely seen as appropriate for lower-value, lower-risk decisions. Today they are embedded in mortgage origination, portfolio monitoring and risk management. So for me, the real shift has been from information scarcity to intelligence-led decision-making.
The challenge for businesses now is no longer simply having more data. Everyone has data. The differentiator is whether you can turn it into trusted intelligence, embed it into the customer journey and use it to solve a real problem. That requires a very different kind of leadership, more curious, more agile and much more willing to challenge how things have always been done.
As artificial intelligence and data analytics become increasingly embedded in property, what opportunities do you see for women to play a greater role in shaping the future of the industry?
There is a wonderful irony here: women are already a hugely influential force in the South African property market. Our latest Lightstone analysis shows that, among non-subsidised properties owned by single individuals, women now outnumber men as sole property owners. In Sectional Title properties, there are around 130 female owners for every 100 male owners.
So women aren't a niche customer segment. We are shaping the market. The opportunity now is to make sure women are equally involved in shaping the technology that serves it. That doesn’t just mean encouraging more women to become software developers. AI and PropTech need people who understand customers, behaviour, risk, finance, data, product and commercial strategy.
I think that creates an enormous opportunity because some of the most interesting careers of the future will sit between traditional disciplines. Technology ultimately reflects the questions asked by the people building it. The more diverse those people are, the more likely we are to challenge assumptions and build products that reflect the market we actually live in.
PropTech is changing how property is valued, bought, sold and managed. How do you balance embracing technological innovation with maintaining the human judgement and relationships that remain so important in property?
I don’t see technology and human judgement as competing forces. The best technology should make humans better at what they do. Take property valuation. Machine learning can analyse millions of data points and identify patterns that no individual could possibly process. But the model still needs to be understood and applied in context.
The same is true for estate agents. Twenty years ago, having access to comparable sales gave an agent an information advantage. Today that information is readily available. So what differentiates a great agent now? Judgement, relationships, negotiation, empathy and understanding the human being sitting across the table.
Buying a home is still an incredibly emotional decision. Nobody buys a house because an algorithm tells them to. They buy because of their family, a school, a neighbourhood, an aspiration or a particular stage of their lives. Technology should remove friction and improve the quality of the decision. Humans provide the context and the trust. The businesses that get that combination right will win.
Women remain underrepresented in many senior leadership and technology roles. What do you think the property industry needs to do differently to ensure that women are not simply users of PropTech, but are among the people designing and leading the technologies that will shape the sector?
For me, the issue isn’t simply getting more women into the industry. It is making sure they are given meaningful opportunities to influence decisions, own products, lead teams and shape strategy. I’m a Chartered Accountant by training. I didn’t follow a traditional technology career, yet today I lead a data and technology business. Increasingly, I think those unconventional career paths are incredibly valuable.
The best technology businesses need people who can connect the technology to the problem being solved. Companies therefore need to actively expose talented women from finance, product, operations, sales, analytics and other disciplines to technology and innovation opportunities.
Mentorship matters, but sponsorship matters even more. At some point somebody has to say: I think she can do this. Give her the opportunity.
And I think we also need to stop confusing confidence with competence. People lead differently, and the loudest voice in the room isn't necessarily the best leader. One idea I feel strongly about is rewarding bravery. You don't need to have every answer. You need the courage to make a thoughtful decision, learn quickly and change course when the evidence tells you to. We need to give more women the opportunity to do exactly that.
Innovation often requires leaders to be comfortable with uncertainty and change. What have your experiences leading Lightstone taught you about creating a culture where people are willing to embrace new technologies and challenge established ways of doing things?
One thing I’ve learnt is that you cannot tell people to “innovate” and expect innovation to happen. You have to create an environment where people feel comfortable challenging the way things have always been done – including challenging the leader. At Lightstone, the test I keep coming back to is quite simple: what problem are we actually solving?
AI makes that question even more important because right now it is incredibly easy to become distracted by what the technology can do rather than what it should do. I want our teams experimenting. I want them trying things that may not work. And I want people bringing forward ideas before they're perfectly formed.
But experimentation doesn’t mean abandoning discipline. We operate in an industry where our technology can influence lending decisions and people's financial futures. Trust, governance and explainability therefore matter enormously. For me, great innovation requires both bravery and discipline: the bravery to challenge what exists and the discipline to build something better in its place.
Looking five years ahead, which emerging PropTech development do you think could have the biggest impact on South Africa’s property market — and why?
I think the biggest opportunity is actually bigger than AI. It is creating a connected property ecosystem.
Today, selling a property, valuing it, securing finance, meeting compliance requirements, conveyancing and registering the transaction are still incredibly fragmented processes. The same information is captured, checked and transferred multiple times between different organisations. That feels increasingly outdated.
AI will absolutely accelerate the change - whether through valuation, computer vision, satellite imagery, automated decision-making or agentic workflows - but AI itself isn’t the destination.
The real prize is allowing trusted information to move seamlessly between the consumer, agent, lender, valuer, attorney and ultimately the registration ecosystem. Imagine taking a process that can currently take months and getting much closer to completing a property transaction in days. That creates enormous efficiencies, but more importantly it could make property simpler and more transparent for ordinary South Africans.
There will still be structural challenges that technology alone cannot fix – affordability, title registration and municipal inefficiencies among them. But five years from now, I hope we're talking less about individual pieces of PropTech and more about how we have connected them to create a property market that is faster, simpler, more transparent and ultimately more trusted.
