Benjamin Tailor

Benjamin Tailor

Digital Insurance Consultant
Benjamin Tailor has extensive experience in the Financial Services industry and is considered authority in Insurtech. He is particularly interested in the potential of AI to enhance claims processing and offers an overview of insurance innovation. His content is packed with insights and tips that provide his audience with key perspectives needed to stay ahead of market trends.
Can Title Agency Negligence Lead to Federal RICO Charges?
Insurance Can Title Agency Negligence Lead to Federal RICO Charges?

Simon Glairy is a formidable voice in real estate risk management and forensic title analysis, having spent decades navigating the complexities of property law and insurance fraud. As an expert who has seen the devastating impact of deed theft firsthand, Glairy provides a unique perspective on the

WTW Expert Warns of AI Transparency Risks for Insurers
Technology & Trends WTW Expert Warns of AI Transparency Risks for Insurers

Simon Glairy is a distinguished authority in the insurance and Insurtech sectors, renowned for his strategic focus on risk management and the integration of artificial intelligence into traditional underwriting frameworks. As the industry grapples with the transition from legacy systems to

Australian Add-On Insurance Claims Hit $3.4 Billion
Insurance Australian Add-On Insurance Claims Hit $3.4 Billion

The Australian financial landscape is currently undergoing a massive recalibration as the fallout from years of aggressive add-on insurance sales culminates in a staggering $3.4 billion liability for major institutions. This movement is largely fueled by specialized claims management firms that

When Does Your 8-Month Medicare Clock Actually Start?
Insurance When Does Your 8-Month Medicare Clock Actually Start?

Transitioning from a professional career to retirement is a significant life milestone, yet many seniors find themselves ensnared by complex administrative rules regarding Medicare enrollment. A common and costly misunderstanding involves the assumption that any health coverage, including COBRA or

Insurers Strategically Integrate AI With Human Oversight
Technology & Trends Insurers Strategically Integrate AI With Human Oversight

The long-standing promise of a fully automated insurance landscape where machines silently process claims and calculate risks without a single human touch remains a distant fantasy in an industry defined by its absolute need for transparency and consistency. While generative AI is capable of

Will AI Erode Human Expertise in the Insurance Industry?
Technology & Trends Will AI Erode Human Expertise in the Insurance Industry?

As artificial intelligence transitions from a speculative curiosity into a core operational driver, the insurance landscape is experiencing a profound shift in how risk is assessed and managed. Simon Glairy, a distinguished voice in insurance and risk assessment, joins us to discuss the delicate

Can Wildfire Survivors Force Insurance Accountability?
Risk Management Can Wildfire Survivors Force Insurance Accountability?

The harrowing experience of escaping a fast-moving wildfire in Los Angeles County often serves as a prelude to a second, more protracted crisis involving the very institutions designed to provide security. While the initial devastation is measured in scorched acres and lost property, the subsequent

Insurance Woes Stall Luxury Tower at Surfside Collapse Site
Regulatory & Compliance Insurance Woes Stall Luxury Tower at Surfside Collapse Site

Simon Glairy stands at the intersection of traditional risk management and the evolving world of Insurtech, bringing years of perspective on how catastrophic events reshape the global insurance landscape. In the wake of the fifth anniversary of the Surfside tragedy, we discuss the current stalemate

Rising Climate Risks Threaten Global Data Center Markets
Insurance Rising Climate Risks Threaten Global Data Center Markets

As the digital world expands at a breakneck pace, the physical infrastructure supporting our AI-driven future is facing an unprecedented collision with environmental reality. Simon Glairy, a distinguished authority in risk management and Insurtech, joins us to unpack the intensifying climate

Why Is the U.S. Sacrificing Healthcare for Tax Cuts?
Insurance Why Is the U.S. Sacrificing Healthcare for Tax Cuts?

The arrival of January 1, 2026, marked a seismic shift in the American domestic landscape as millions of low and middle-income families woke up to find their health insurance premiums had suddenly become entirely unaffordable. This immediate crisis stems from the expiration of federal tax credits

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