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

In this episode of Making Risk Flow, Jake Harding sits down with Izik Lavy and Jacob Grob from GeoX AI to explore how property intelligence is transforming insurance underwriting. They discuss how accurate geospatial data, computer vision, and confidence-scored models help carriers move beyond reactive decision-making, accelerate quotes, uncover profitable opportunities, and better manage risk. The conversation explores why deterministic data can outperform probabilistic AI, how deeper property insights reveal hidden value in complex markets, and why specialized technology providers are becoming essential partners for insurers. Discover how real-time property intelligence is reshaping portfolio strategy, pricing, and the future of insurance. 

Izik Lavy is the CEO and co-founder of GeoX AI, a geospatial intelligence platform specializing in property data extraction and analysis for the insurance industry. With 15 years of experience in geospatial technology and expertise in building scalable computer vision solutions, Lavy has led GeoX's expansion from the Japanese and Australian markets into the United States.

Jacob Grob is the EVP of Sales for US Markets at GeoX, bringing 20 years of insurance data expertise to the conversation. Previously a senior leader at CoreLogic, where he gained deep exposure to building characteristics, catastrophe modeling, and replacement cost data, Grob now focuses on solving critical data blind spots through computer vision and scalable AI.

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 Kristoffer Lundberg, CEO of Insurtech Insights, to explore how AI is transforming insurance from a story of disruption into one of collaboration. Recorded at InsureTech Insights in New York, the conversation examines what it takes to deploy AI at scale, from defining clear business goals and building the right partnerships to redesigning operating models around automation. 

Kristoffer shares lessons from real-world AI implementations, including claims transformation, and explains why insurers must “think slow, execute fast” to create lasting value. The episode reveals how ecosystem partnerships, human-centered design, and measurable outcomes will shape the next era of insurance innovation. 

Kristoffer Lundberg is the CEO of Insurtech Insights, a global insurance technology community connecting insurers, startups, investors, and technology leaders to accelerate innovation across the industry. Since joining Insurtech Insights in 2018, Kristoffer has helped grow the platform into a leading global destination for insurance transformation, hosting major conferences across Europe, the U.S., and Asia. His work focuses on bringing industry stakeholders together to explore emerging technologies, collaboration, and the future of 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

In this episode of Making Risk Flow, Juan de Castro sits down with Greg Brown, Partner at Oxbow Partners, to explore the strategic choices reshaping the London insurance market. As market conditions soften and technology advances accelerate, Greg explains why firms must clearly define whether they are true leaders, niche leaders, capacity leaders, or followers, and align their operating models accordingly. 

The conversation examines how misalignment between market position and business architecture can erode profitability and competitive advantage. Greg also discusses the growing importance of portfolio management, the evolution of facilities from cyclical tools to permanent market infrastructure, and the role of AI in enhancing underwriting decision-making. 

Greg Brown is a Partner at Oxbow Partners, a strategic advisory firm focused exclusively on the insurance industry. He specializes in helping Lloyd's and London Market organizations navigate strategic transformation, from underwriter modernization to launching digital business units. Combining expertise in strategy, operations, and technology, Greg helps insurers develop ambitious, practical plans that drive sustainable growth and 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 your climate risk assessments could predict the future with greater accuracy than historical data alone?

In part two of this conversation on Making Risk Flow, Jake Harding continues his discussion with Joan Saladich, Founder of Geoskop, exploring how insurers can move beyond static climate risk models and embrace a more sophisticated, forward-looking approach to decision-making. Joan explains why annual climate model updates can create misleading conclusions, how vegetation and soil dynamics reshape wildfire risk, and why relying on single-source data leaves carriers exposed to blind spots. 

The conversation also examines the role of AI and large language models in processing complex climate datasets, emphasising that technology should enhance, not replace, human judgment. Joan outlines a practical framework for combining historical data, future climate projections, alternative statistical models, and socioeconomic context to generate more accurate, explainable, and actionable climate risk intelligence. 

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 climate risk data you're using to underwrite policies is fundamentally flawed?

In this first of two-part episode of Making Risk Flow, host Jake Harding speaks with Joan Saladich, CEO and co-founder of Geoskop, about why traditional climate risk scores often fail insurers and what a more sophisticated approach looks like. Joan explains how deterministic ratings and traffic-light systems oversimplify complex climate realities, making them unsuitable for underwriting decisions. He explores the value of probabilistic climate modeling, AI-powered analysis, and uncertainty quantification in assessing evolving risks. 

The conversation also examines changing reinsurance dynamics, which are pushing more climate-related exposure onto commercial insurers. Joan discusses the importance of validating climate models through measurable accuracy and transparency, while highlighting how outdated scenario assumptions can distort risk assessments. Together, they show how embracing data complexity can create a meaningful competitive advantage in modern insurance underwriting. 

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