Introduction

AI is already changing underwriting, but is the industry focusing on the part of the job where it can create the most value?

In this episode, Matthew Grant speaks with Jamie Wilson, VP of Strategy at hyperexponential, about the evolution of underwriting technology, the move from AI-assisted tools towards agentic workflows and what 350 senior underwriters across the UK and US say they actually want from AI.

Jamie explains why much of the value delivered by AI so far has been concentrated on efficiency and reducing manual administration. Yet when underwriters were asked what makes someone exceptional at their job, speed barely featured. Instead, they pointed to qualities such as risk selection, technical depth, judgement and commercial instinct. It raises an important question: rather than simply helping underwriters work faster, can AI help them make better decisions?

The conversation explores what changes as underwriting moves from AI-assisted to agentic. Instead of an underwriter controlling the workflow and calling on AI for individual tasks, an agentic system can move work through the underwriting process itself, involving a human when a decision requires expertise or falls outside predefined guardrails. Jamie discusses why those guardrails will be critical and how different portfolios could require very different levels of human involvement.

They also examine the implications for underwriting teams. As technology takes on more routine work, experienced underwriters could spend more time applying their expertise to complex risks, while technical portfolio teams may play a growing role in determining where and how greater autonomy should be used.

Finally, Jamie shares one of the most striking findings from the research: the "succession paradox". Underwriters identified the loss of senior judgement before it can be passed to the next generation as their biggest future concern, yet coaching junior colleagues ranked last among the investment priorities explored in the survey. Could AI help bridge that gap by making accumulated underwriting knowledge and expertise more accessible to the next generation?

In this episode you’ll learn:

• Why focusing on efficiency alone could underestimate the potential of AI in underwriting
• What underwriters believe separates exceptional underwriting from simply working faster
• The difference between AI-assisted and agentic underwriting
• How guardrails can determine when an AI agent acts autonomously and when an underwriter steps in
• Why different portfolios may require very different approaches to agentic underwriting
• How greater automation could allow underwriters to focus their expertise on more complex risks
• Why existing technology architecture and point solutions could complicate end-to-end agentic workflows
• What the "succession paradox" reveals about the industry's approach to developing junior underwriting talent
• How AI could potentially help transfer expertise from experienced underwriters to the next generation

Book recommendation:

• Thinking, Fast and Slow by Daniel Kahneman for its insights into human judgement, data-driven decision-making and the psychology of adopting new technology.

Read hyperexponential's Underwriting Edge Report

Discover what 350 senior commercial P&C underwriters say defines underwriting excellence, where AI is delivering value and what could hold the industry back in hyperexponential’s Underwriting Edge 2026 report.

Curious for more? Catch-up with all that happened at hx Live NYC on 17 September.

If you like what you’re hearing, please leave us a review on whichever platform you use or contact Matthew Grant on LinkedIn.

Sign up to the InsTech newsletter for a fresh view on the world every Wednesday morning.

Introduction

Facultative reinsurance can give insurers the additional capacity they need to write risks they might otherwise decline. But for smaller, more transactional placements, its value increasingly depends on how quickly that capacity can be accessed.

Joining Matthew Grant on the podcast, Dom Sindall, Head of Digital Broking, Facultative at Marsh Re, and Stephen Sheehan, Head of Analytics, Facultative at Marsh Re, explain how digital trading, automation and better data could reduce facultative placement times from days to hours or even minutes.

Dom explains why much of the delay in facultative reinsurance comes not from the work itself, but from the elapsed time between people completing each stage of a placement. Removing some of those dependencies could make facultative reinsurance significantly more accessible for smaller risks, where speed can matter more than price.

The discussion explores how advances in AI are helping automate another source of friction: insurance data. Stephen explains how extracting policy information from documents has become increasingly straightforward, while exposure data remains more challenging. Schedules of values (SOVs) can contain dozens of tabs, multiple currencies and inconsistent terminology, making ingestion, standardisation and quality control critical parts of the automation process.

They also examine where humans should remain involved. Fully automated workflows offer greater speed, but Dom and Stephen explain why firms need to determine what level of data quality is ‘good enough’, where validation gates are required and which capabilities should be built internally or bought from technology partners.

Looking ahead, Dom explains why the growth of digital trading could expand the facultative market itself. Reinsurers that invested early in data standards have been able to move quickly, while the next wave may increasingly look to partnerships to accelerate their own digital capabilities.

In this episode you’ll learn:

• Why speed is becoming increasingly important for smaller facultative placements
• How automation could reduce placement times from days to hours or minutes
• Why AI has made extracting policy data significantly easier
• Why exposure data remains a more difficult automation challenge
• How to decide where human validation belongs within automated workflows
• Why ‘good enough’ data can be more commercially valuable than pursuing perfection
• How insurers and brokers can approach build versus buy technology decisions
• Why early investment in data standards is creating an advantage in digital trading
• How reducing friction could help grow the facultative reinsurance market

Book recommendations:

• Stephen Sheehan: Don’t Believe Everything You Think by Joseph Nguyen
• Dom Sindall: The Innovator’s Dilemma by Clayton Christensen

If you like what you’re hearing, please leave us a review on whichever platform you use or contact Matthew Grant on LinkedIn.

Sign up to the InsTech newsletter for a fresh view on the world every Wednesday morning.

Insurers are moving quickly from asking what AI can do to asking how they can actually make it work in underwriting. But experimenting with AI is one thing. Running it reliably across an insurance business is another.

In this episode, Matthew Grant speaks with Andy Moss, GM Underwriting at Duck Creek and former Co-founder and CEO of Send, following Duck Creek’s acquisition of the underwriting technology business.

Andy explains why successful enterprise AI needs to run “on rails”, supported by the infrastructure, governance and workflows required to move beyond proofs of concept and into production. He explores how underwriting workbenches are evolving into orchestration engines and why that shift could become increasingly important as insurers begin introducing AI agents into their workflows.

The conversation also examines a growing challenge for the industry: how to preserve underwriting knowledge as experienced professionals retire. With underwriting becoming more complex, Andy argues that insurers need to codify the processes, referrals and institutional knowledge that often still exist in people’s heads, creating a technology foundation that can support both underwriters and AI.

They also discuss how insurers should approach the increasingly important question of whether to build or buy technology. Andy’s advice is simple: “Buy the commodity and build the differentiators.” Rather than recreating established systems, insurers have an opportunity to focus their development efforts on the data, processes and underwriting expertise that genuinely give them an advantage.

Finally, Andy shares the story behind Send’s acquisition by Duck Creek, how a search for growth investment became an acquisition in around 120 days and what building and selling Send taught him about the importance of assembling a team that genuinely cares about the problems customers are trying to solve.

In this episode you’ll learn:

• Why enterprise AI needs to run “on rails” to succeed in underwriting
• How underwriting workbenches are evolving into orchestration engines
• Why AI proofs of concept can struggle to make the transition into production
• How agentic AI could change underwriting workflows and automate previously manual tasks
• Why capturing institutional knowledge is becoming increasingly urgent as experienced underwriters retire
• How technology can codify the processes and knowledge that currently sit inside underwriting teams
• Why insurers should “buy the commodity and build the differentiators”
• Where internal technology teams can create the greatest competitive advantage
• What bringing underwriting orchestration and core insurance systems together could enable
• How Send’s search for growth funding developed into its acquisition by Duck Creek
• Why Andy believes shared values and genuine commitment to customers were critical to building Send

Andy’s recommendations:

• Invest Like the Best with Patrick O’Shaughnessy
• Desert Island Discs

Read InsTech's recent report with Send on 'Underwriting orchestration engines: equipping insurers for the AI age' here.

Register for InsTech's upcoming 7 October Evening Event with Send and Duck Creek here: Bridging between the islands of automation.

If you like what you’re hearing, please leave us a review on whichever platform you use or contact Matthew Grant on LinkedIn.

Sign up to the InsTech newsletter for a fresh view on the world every Wednesday morning.