SecondSight Raises Series A and Names Insurance Veteran Jamie Bouloux as President

The investment comes as insurers move past general-purpose AI toward systems built on their own data

BLOOMINGTON, Ind. - Oct. 5, 2026 - SecondSight, the AI operating system built for insurance, has raised its Series A and appointed Jamie Bouloux, former CEO of Ryan Financial Lines and Celerity Risk, as President. Backed by investors with deep insurance-market experience, the funding will accelerate organizational growth and product development as SecondSight extends beyond its cyber origins into additional lines of business.

SecondSight’s operating system, SHAPE, learns continuously from insurers’ own data and live external signals, revealing how risks connect and evolve at the speed of the market. Grounded in traceable evidence, its intelligence helps brokers, underwriters and executives anticipate exposures and act on growth opportunities.

SecondSight works with some of the world’s largest insurers to reimagine the insurance lifecycle for an AI-powered market. Its operating system goes beyond automation to inform decisions across distribution, underwriting and reinsurance, helping teams grow premium efficiently, improve loss ratios and allocate capital more strategically.

Bouloux brings nearly two decades of experience in insurance and technology, with deep expertise in cyber, underwriting and specialty insurance. As President, Bouloux will lead SecondSight’s commercial strategy and client relationships, and oversee its growing team of insurance leaders.

“Jamie has built and run the businesses we serve. He understands how decisions at the underwriting desk translate into portfolio performance and where technology needs to create value,” said Reuben Vandeventer, CEO of SecondSight. “He’ll lead our expansion into more lines of business, alongside people who know these markets.”

Bouloux Joins as President

Bouloux was most recently CEO of Ryan Financial Lines and Celerity Risk, leading businesses spanning cyber and financial lines. Before that, he spent eight years as the founder and CEO of EmergIn Risk, a London and US cyber insurance MGA. Earlier, he led CFC Underwriting’s large corporate cyber facility and held leadership roles at AIG, including Head of Cyber and Technology, Media and Telecom Liability for Europe, the Middle East and Africa, where he helped develop the company’s international cyber product and strategy.

“I’ve spent my career underwriting risk and building insurance businesses, often making decisions while the book was still moving,” said Bouloux. “What drew me to SecondSight is the visibility that doesn’t exist anywhere else. My focus is helping insurance teams see and understand what their own data is telling them and act on it with greater precision.”

The Visibility Gap

Insurance is the original science of seeing the future. Every policy is a promise priced against what might happen next. The professionals who price these promises are among the most sophisticated minds in finance, but their tools were built for a slower world. The information they need to understand risk is still split across systems, teams and stages of the insurance lifecycle.

The pressure to fix that is rising. KPMG research found that 77% of insurance leaders surveyed said failing to redesign their enterprise architecture for AI will undermine competitiveness within five years.

General-purpose AI can’t close that gap on its own. Large language models (LLMs) can interpret documents and speed up routine work, but insurance decisions require quantitative analysis of an insurer’s own premiums, claims and exposures, backed by traceable evidence.

Quantitative AI, Purpose-Built for Insurance

SecondSight’s technical approach starts with relationships that broad averages and conventional segmentation can obscure. SHAPE combines algebraic geometry and topological methods, mathematical techniques that reveal the underlying “shape” of complex data, with purpose-built deep learning. Its Large Quantitative Model (LQM) architecture learns from the numerical and structural relationships in policies, premiums, claims and exposures.

The system organizes those records into a map of interconnected risk groups and tracks how it shifts. An embedded model factory trains specialized models on that map for specific lines, segments and decisions, and simulates how the portfolio could change. Language models help users ask questions, but the risk analysis comes from quantitative models trained on the customer’s own data.

Underwriters and portfolio leaders can investigate concentrations, trace findings back to the policies behind them, and test changes to pricing, appetite or exposure limits. Portfolio structures are reproducible from the same inputs and settings, forecasts communicate uncertainty, and model updates require validation and human approval before production use.

SHAPE works with existing core infrastructure and adapts to each organization’s products, workflows and underwriting strategy. Customers own the models trained on their data, including model weights and audit trails, within isolated customer environments.

The result is what SecondSight calls “insurance alpha”: the ability to understand risk more precisely, see it sooner and translate that knowledge into action.

Built by Insurance Insiders

SecondSight pairs tenured insurance operators from underwriting, broking and portfolio management with PhD researchers in mathematics and data science, and its methods are grounded in research published with Indiana University.

Bouloux is the first of several senior insurance leaders SecondSight will introduce in the coming weeks.

To learn more, visit https://www.secondsight.ai/

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About SecondSight

SecondSight is the AI operating system built for insurance. SHAPE combines specialized quantitative models with insurance workflows to help brokers, underwriters and executives understand risk, manage portfolios, and inform growth and capital decisions. Built by insurance operators and PhD researchers, SecondSight works with existing core infrastructure and gives customers ownership of the models trained on their data. Visit the SecondSight website to learn more and connect on LinkedIn.