In this Greatest Hits episode of Making Risk Flow, host Jake Harding speaks with Bryan Falchuk, author of the Future of Insurance series, about why insurance’s next competitive edge lies in intelligence, not efficiency. Bryan argues that carriers focus too heavily on operational optimisation when profitability depends on understanding and managing loss ratios. He introduces the “how might we” mindset as a way to break through cultural resistance and reframe constraints as opportunities. 

The conversation explores AI as a bridge between legacy systems and modern analytics, enabling transformation without massive system overhauls. Bryan also examines how misaligned incentives, complacency, and leadership hubris quietly undermine long-term strategy. Ultimately, he makes the case that curiosity, humility, and proactive risk intelligence will define the insurers that thrive in an era of rapid technological change.

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, host Juan de Castro brings together eight leaders from across insurance, technology, insurtech, and brokerage to explore how AI, operating model transformation, and modern technology architecture are reshaping the future of insurance.

Ann Haug, David McMillan, Christian Stobbs, Kristoffer Lundberg, Greg Brown, Sam Lewis, Allison Hamilton, and Nick Zerbib examine why insurers need more than new technology to gain a competitive advantage. The discussion explores building operating models for scale, creating decision-led technology architectures, accelerating underwriting workflows, and using AI to augment human judgment rather than simply automate existing processes.

The group also considers AI-driven claims transformation, intelligent submission routing, the future role of underwriters, customer obsession, and how brokers can prepare for growing market and private equity pressures. Together, these perspectives reveal how culture, technology, speed, and strategic clarity can help insurers become more agile, scalable, and resilient in an increasingly competitive market.

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 Greatest Hits episode of Making Risk Flow, host Juan de Castro is joined by Jean-Jacques Henchoz (JJ), Non-Executive Director, Brit Insurance, and a non-executive director across the insurance value chain, to explore the future of insurance. With over 25 years of industry experience, JJ shares his perspectives on how insurers can remain relevant by addressing protection gaps, improving affordability, and embracing cultural and technological transformation. 

The discussion highlights how AI, automation, and innovation are reshaping customer experience while reducing inefficiencies. Juan and JJ also examine the importance of attracting tech-savvy talent, breaking down silos, and fostering collaboration across the sector. Packed with insights, this conversation offers a roadmap for insurers seeking to stay customer-centric and resilient in a rapidly evolving world.

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, host Jake Harding brings together ten leaders from across insurance, data, and technology to explore how spatial intelligence, real-time data, and climate modeling are reshaping risk assessment and underwriting. 

Mark Varley, Simon De La Hoyde, Izik Lavy, Jacob Grob, Joan Saladich, Caroline Grey, Pierre-Henri Janssens, Bryan Falchuk, Jay Wallace, and Nick Franz examine why insurers need more than greater data volumes to gain an advantage. The discussion explores point-of-quote accumulation, property-level geospatial analysis, probabilistic climate intelligence, and the value of embedding spatial context early in underwriting workflows. 

The group also considers emerging opportunities in post-binding cyber intervention and agricultural risk data, while examining how integrated technology, proactive portfolio analysis, and clean-sheet thinking can improve risk selection, profitability, and long-term competitive advantage across insurance markets.

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 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