Simon Glairy has spent years in the engine room of insurance operations and Insurtech, shaping risk programs and advising boards through sensitive leadership transitions. In this conversation, he unpacks how a confidential investigation, a rapid reinstatement, and the redundancy of a newly
Setting the Stage for a Market Shift in Auto Insurance Imagine a scenario where a car accident leaves a New Jersey driver with a totaled vehicle, only to face a settlement offer from their insurer that barely covers half the car’s worth. This kind of dispute over valuation is far from rare, and it
Simon Glairy has spent his career at the intersection of insurance, risk management, and Insurtech. He helps boards and security leaders translate technical threats into business decisions, and his work on AI-driven risk assessment has shaped how companies evaluate and transfer cyber risk. In this
When a breach knocks core systems offline, the headline fades fast while hidden costs and compound risks accelerate across operations, customers, and regulators. That acceleration is shaping budgets, insurance buying, and board agendas, yet a striking divergence persists between rising concern and
Boardrooms are betting on algorithms that learn faster than policies can adapt, and cyber insurance is where that wager is already being called in real time. The promise is unmistakable: cleaner underwriting signals, faster claims, smarter pricing, and less friction across customer journeys. Yet
Small businesses with lean teams and tight margins have increasingly found that a single cyber incident can knock out core systems, disrupt sales, and trigger a costly scramble to recover, even when the breach started with nothing more than a phish or a misconfigured account exposed to the
