Making Risk Flow | The Future of Insurance

In this Greatest Hits episode of Making Risk Flow, we revisit host Juan de Castro’s conversation with David McMillan, former CEO of esureGroup, to unpack how a mid-sized insurer reinvented itself under private equity ownership. Facing COVID-19, reserve pressures, a soft market, and geopolitical disruption, the company leaned into culture, clarity, and modern technology to outpace larger rivals. David shares why building a high-performing team starts with shared values, how blending insurance expertise with external digital talent accelerates innovation, and why cloud-native, API-driven architecture is essential for real-time decision-making. 
He also explains how to shift boards from traditional ROI forecasts to agile, outcome-based governance. It’s a candid conversation about resilience, leadership under pressure, and why staying smaller, more agile, and hence, faster can be a lasting competitive advantage.

Fan Mail: Got a challenge digitizing your intake? Share it with us, and we’ll unpack solutions from our experience at Cytora.
To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'.

Our previous guests include: Bronek Masojada of PPL, Craig Knightly of Inigo, Andrew Horton of QBE Insurance, Simon McGinn of Allianz, Stephane Flaquet of Hiscox, Matthew Grant of InsTech, Paul Brand of Convex, Paolo Cuomo of Gallagher Re, and Thierry Daucourt of AXA.

Check out the three most downloaded episodes:
The Five Pillars of Data Analytics Strategy in Insurance | Craig Knightly, Inigo
20 Years as CEO of Hiscox: Personal Reflections and the Evolution of PPL | Bronek Masojada
Implementing ESG in the Insurance and Underwriting Space | Simon Tighe, Chaucer, and Paul McCarney, Moody's

What if operational excellence wasn't about cutting costs, but about unlocking your organization's true potential?
In this episode of Making Risk Flow, Juan de Castro speaks with Ann Haugh, Group Chief Operations Officer at Axis Capital, about why operations should be viewed as a strategic growth engine rather than a cost center. Ann shares how Axis transformed its operating model to improve efficiency while scaling the business, the importance of building cross-functional talent, and how leaders can create alignment across technology, data, and underwriting. 
She also explores the role of AI in specialty insurance, explaining how automation can enhance employee experience, empower underwriters to make better decisions, and help organizations grow with greater speed, clarity, and resilience.
Ann Haugh is Group Chief Operations Officer at Axis Capital and a global (re)insurance leader with more than 30 years of experience spanning strategy, underwriting, operations, and general management. She has led transformational programs, improved underwriting performance, driven profitable growth, and built high-performing teams worldwide, earning a reputation for inspirational leadership, innovation, and delivering lasting business impact.
Fan Mail: Got a challenge digitizing your intake? Share it with us, and we’ll unpack solutions from our experience at Cytora.
To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'.

Our previous guests include: Bronek Masojada of PPL, Craig Knightly of Inigo, Andrew Horton of QBE Insurance, Simon McGinn of Allianz, Stephane Flaquet of Hiscox, Matthew Grant of InsTech, Paul Brand of Convex, Paolo Cuomo of Gallagher Re, and Thierry Daucourt of AXA.

Check out the three most downloaded episodes:
The Five Pillars of Data Analytics Strategy in Insurance | Craig Knightly, Inigo
20 Years as CEO of Hiscox: Personal Reflections and the Evolution of PPL | Bronek Masojada
Implementing ESG in the Insurance and Underwriting Space | Simon Tighe, Chaucer, and Paul McCarney, Moody's

What if the insurance industry could move at the speed of modern technology?
In this episode of Making Risk Flow, Christian Stobbs, we revisit one of our top episodes of 2026 where Juan de Castro sits down with Christian Stobbs, Chief Strategy & Corporate Development Officer at Markel, joins host Juan de Castro to discuss what it takes to build a preeminent specialty insurer in an increasingly technology-driven market. Christian explains why speed, customer obsession, technical expertise, and principled decision-making must work together as a unified competitive advantage. 
The conversation explores how insurers can localize strategy across international markets, reduce costly operational inefficiencies, and deploy AI to enhance underwriting and claims without losing critical human judgment. Christian also shares why transformational technology initiatives should operate with startup-style urgency, how AI will reshape underwriting roles, and why the insurers that adapt fastest will define the future of specialty insurance. 

Fan Mail: Got a challenge digitizing your intake? Share it with us, and we’ll unpack solutions from our experience at Cytora.
To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'.

Our previous guests include: Bronek Masojada of PPL, Craig Knightly of Inigo, Andrew Horton of QBE Insurance, Simon McGinn of Allianz, Stephane Flaquet of Hiscox, Matthew Grant of InsTech, Paul Brand of Convex, Paolo Cuomo of Gallagher Re, and Thierry Daucourt of AXA.

Check out the three most downloaded episodes:
The Five Pillars of Data Analytics Strategy in Insurance | Craig Knightly, Inigo
20 Years as CEO of Hiscox: Personal Reflections and the Evolution of PPL | Bronek Masojada
Implementing ESG in the Insurance and Underwriting Space | Simon Tighe, Chaucer, and Paul McCarney, Moody's

Geospatial intelligence is changing the way insurers assess risk, but better decisions start with better data. 
In this episode of Making Risk Flow, Jake Harding is joined by Mark Varley, CEO of Addresscloud, and Simon de la Hoyde, Sales Director, to discuss how building-level data, real-time accumulation visibility, and high-quality address intelligence help underwriters quote faster, select risks with greater confidence, and write more profitable business. They also explore why insurers should focus on data quality before AI, how specialized data platforms outperform in-house solutions, and how responsible AI can enhance underwriting without compromising accuracy, transparency, or governance. 
Mark Varley is CEO of Addresscloud, a geospatial intelligence platform serving the insurance industry. With 25 years of experience in insurance and 15+ years specializing in geographic risk assessment, Mark brings deep practitioner insights from his tenure at RSA and Accenture.
Simon de la Hoyde is Sales Director at Addresscloud, bringing 17 years of insurance market expertise and a foundational background in geography and GIS applications. With experience across mobile telecommunications, retail site selection, and property insurance underwriting and pricing, de la Hoyde combines technical geospatial knowledge with deep commercial insurance acumen.

Fan Mail: Got a challenge digitizing your intake? Share it with us, and we’ll unpack solutions from our experience at Cytora.
To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'.

Our previous guests include: Bronek Masojada of PPL, Craig Knightly of Inigo, Andrew Horton of QBE Insurance, Simon McGinn of Allianz, Stephane Flaquet of Hiscox, Matthew Grant of InsTech, Paul Brand of Convex, Paolo Cuomo of Gallagher Re, and Thierry Daucourt of AXA.

Check out the three most downloaded episodes:
The Five Pillars of Data Analytics Strategy in Insurance | Craig Knightly, Inigo
20 Years as CEO of Hiscox: Personal Reflections and the Evolution of PPL | Bronek Masojada
Implementing ESG in the Insurance and Underwriting Space | Simon Tighe, Chaucer, and Paul McCarney, Moody's

In this episode of Making Risk Flow, Juan de Castro sits down with Allison Hamilton, US Customer Success Lead at Applied Systems, to discuss why underwriting transformation depends on people and processes as much as technology. Allison explains how better data governance, transparent AI, and aligned incentives help underwriters make faster, more confident decisions. 
She explores why speed-to-quote has become a critical competitive advantage, how broker integration and third-party data remove costly friction, and why decision-ready workflows, not full automation, will define the winning carriers of 2030. The conversation offers practical insights for insurers modernizing underwriting in an AI-driven world. 
Allison Hamilton is Head of US Customer Success for Cytora, a division of Applied Systems, where she leads customer delivery, adoption, and long-term value across North America. She partners with insurers to modernize underwriting through workflow automation, digital risk processing, and operating model innovation. Allison oversees strategic customer programs, drives measurable business outcomes, and works closely with product and go-to-market teams to shape Cytora's US strategy. 

Fan Mail: Got a challenge digitizing your intake? Share it with us, and we’ll unpack solutions from our experience at Cytora.
To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'.

Our previous guests include: Bronek Masojada of PPL, Craig Knightly of Inigo, Andrew Horton of QBE Insurance, Simon McGinn of Allianz, Stephane Flaquet of Hiscox, Matthew Grant of InsTech, Paul Brand of Convex, Paolo Cuomo of Gallagher Re, and Thierry Daucourt of AXA.

Check out the three most downloaded episodes:
The Five Pillars of Data Analytics Strategy in Insurance | Craig Knightly, Inigo
20 Years as CEO of Hiscox: Personal Reflections and the Evolution of PPL | Bronek Masojada
Implementing ESG in the Insurance and Underwriting Space | Simon Tighe, Chaucer, and Paul McCarney, Moody's