Making Risk Flow | The Future of Insurance

Cytora

Making Risk Flow is a podcast powered by Cytora. This insurance podcast is designed to bring clarity, know-how and inspiration in driving digital transformation for commercial insurers, paying particular attention to the automation of risk processing. This podcast, led by industry veteran Juan de Castro as well as insurance change-makers, will showcase their learnings, challenges and solutions that have, or haven’t, worked for them. If you are embarking on leading a transformational project in your insurance company and want to make sense of it all - this podcast is for you.

To discover out more about digital risk processing, visit https://www.cytora.com

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20 episodes
Updated Tuesday

Episodes20

Newest first

Tuesday · 39 min
[Greatest Hits] Re-Architecting Insurance for Speed, Data and Resilience | David McMillan, Jensten
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
July 29 · 37 min
Why Operations Is the Ultimate Growth Engine in Insurance | Ann Haugh
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
July 21 · 40 min
[Greatest Hits] The Speed Advantage: How AI and Customer Obsession Are Reshaping Specialty Insurance | Christian Stobbs
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
July 14 · 34 min
Why Better Data Helps Underwriters Say 'Yes' More Often | Mark Varley & Simon de la Hoyde
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
July 9 · 33 min
Beyond Automation: The Real Drivers of Underwriting Transformation | Allison Hamilton
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
June 30 · 39 min
Property Intelligence at Scale: How Geospatial Data Is Redefining Insurance Underwriting | Izik Lavy and Jacob Grob
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
June 23 · 32 min
Think Slow, Execute Fast: The New Playbook for Vertical AI Transformation in Insurance | Kristoffer Lundberg
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
June 16 · 41 min
Lead, Follow, or Fall Behind? Positioning for Success in the Insurance Market | Greg Brown
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
June 9 · 29 min
Beyond Traffic-Light Risk Scores: Building Climate Risk Models That Actually Work | Joan Saladich (Part 2)
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
June 2 · 26 min
Beyond Traffic-Light Risk Scores: Building Climate Risk Models That Actually Work | Joan Saladich (Part 1)
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
May 26 · 35 min
Why Climate Data is Forming the Risk Intelligence Blueprint for Commercial Insurance | Caroline Grey
What if the data you needed to price complex agricultural risks were available in near-real time instead of months later? In this episode of Making Risk Flow, host Jake Harding speaks with Caroline Grey, co-founder and CRO at Treefera, about how satellite imagery, AI, and scientific modelling are reshaping the future of insurance risk assessment. Caroline explains why the industry is moving beyond broad regional assumptions towards plot-level intelligence that enables faster underwriting, more accurate pricing, and entirely new insurance products. The conversation explores how insurers can use near-real-time agricultural and climate data to reduce claims exposure, improve operational efficiency, and respond proactively to supply chain volatility. Caroline also shares practical guidance on structuring complex datasets for different business stakeholders, building scalable partnerships, and validating new solutions through low-risk pilots. This episode offers valuable insight into how data-driven underwriting is creating a competitive advantage across commercial 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
May 19 · 40 min
The Speed Advantage: How AI and Customer Obsession Are Reshaping Specialty Insurance | Christian Stobbs
What if the insurance industry could move at the speed of modern technology? In this episode of Making Risk Flow, 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
May 12 · 35 min
Making Risk Flow Special Edition | 5 Insurance Leaders on Winning the AI Transformation Race
In this special compilation episode of Making Risk Flow, we bring together five standout conversations exploring how agentic AI, digital transformation, and organizational culture are reshaping the insurance industry. Featuring insights from leaders including Antonio Grimaldi of McKinsey & Company, Sam Lewis, Nicolas Zerbib, Richard Hartley, Bill Harris & Drake Slaikeu-Lawhead, the episode examines why AI leaders are generating dramatically stronger returns than competitors and how technologies like stateful agents, spatial intelligence, and headless orchestration are changing underwriting and distribution. Beyond technology itself, the discussion highlights the cultural shifts required to unlock transformation at scale. From reducing workflow friction to improving underwriting precision and scaling operations without proportional hiring, this episode offers practical frameworks for carriers, brokers, and tech leaders navigating insurance’s next era. 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
May 5 · 44 min
Risk, Reimagined: 11 Experts on Turning Data into Decisions
This “Best of the Year Thus Far” episode of Making Risk Flow brings together 11 standout conversations that map how insurance is being reshaped in real time. Across the conversations with AI leaders, risk modelers, and operators, a clear pattern emerges: the gap between leaders and laggards is widening, driven by speed of execution, not just strategy. Industry leaders explore how richer context, whether through spatial intelligence, stateful systems, or agentic workflows, is transforming underwriting from a static, data-driven exercise into a dynamic, decision-driven discipline. But technology alone isn’t the answer. Culture, incentives, and human relationships remain critical to unlocking value. Together, these insights reveal an industry shifting from managing risk as a probability to understanding it as a living, evolving system. 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
April 28 · 32 min
The Real-Time Data Edge: Why Speed and Accuracy Beat Volume in Underwriting | Pierre-Henri Janssens
What if real-time data and AI could transform compliance from a regulatory burden into a competitive advantage? In this episode of Making Risk Flow, Pierre-Henri Janssens, CEO and Cofounder of Topograph, joins host Jake Harding to rethink compliance in insurance from first principles. They discuss why treating compliance as a regulatory burden limits growth, while real-time data and transparent workflows turn it into a competitive advantage. Pierre-Henri explains how connecting directly to official registries improves data accuracy, how vertical AI enhances document extraction, and why prioritizing high-impact signals prevents data overload. The conversation also explores the build-versus-buy dilemma, the complexity of scaling across jurisdictions, and how orchestrating best-in-class solutions accelerates onboarding and improves conversion. It’s a pragmatic look at how insurers can transform compliance into measurable business value. 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
April 21 · 45 min
The Iteration Trap: Why 'Improving' Your Underwriting is Killing Your Growth | Bryan Falchuk
What if insurance workflows could evolve faster than regulation itself? In his third appearance on Making Risk Flow, Bryan Falchuk, best-selling author, speaker, life coach and President and CEO of PLRB, joins host Jake Harding to rethink modernization of Insurance from first principles. They discuss why layering AI onto legacy systems only reinforces the iteration trap, while agentic AI enables carriers to redesign processes around real-time data orchestration. Bryan explains why implementation can shrink from years to weeks, how orchestration replaces brittle workbenches, and why design thinking is the unlock for cultural change. The conversation also explores the shifting role of underwriters and claims professionals, from data processors to strategic advisors. It’s a clear-eyed look at how insurers can build adaptive, future-ready operations without wholesale system replacement today. 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
April 14 · 40 min
Beyond CVSS: The New Cyber Underwriting Playbook | Jay Wallace of VulnCheck
In this episode of Making Risk Flow: Exploring the Ecosystem, host Jake Harding sits down with Jay Wallace of VulnCheck about how real-time exploit intelligence is reshaping cyber insurance. They unpack why traditional CVSS scoring falls short and how modeling threat actor behaviour offers a clearer picture of risk. Jay explains how carriers can use machine-readable data feeds to automate underwriting and continuously monitor exposure post-binding. The conversation also highlights the value of proactive threat notifications in reducing claims and strengthening client trust. Jay and Jake also explore how AI and automation enhance, not replace, analysts, and why the most successful insurers are shifting from a profit-centric mindset to a partnership-driven approach focused on prevention, resilience, and long-term value creation. 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
April 7 · 37 min
The Broker Edge in an AI-Driven Insurance Market | Nicolas Zerbib of Stonepoint Capital
In this episode of Making Risk Flow: Exploring the Ecosystem, host Juan de Castro sits down with Nicolas Zerbib, Co-President and CIO at Stone Point Capital, to unpack how AI is reshaping, not replacing, the insurance brokerage model. Nick explains why retention and complexity remain the strongest defenses against disruption, and how brokers can use AI to improve efficiency without losing their edge. From reducing operating costs to enhancing onboarding and preserving institutional knowledge, AI emerges as a powerful enabler rather than a threat. The conversation also highlights the structural advantages of the broker channel, including regulatory accountability and E&O risk, which AI cannot easily replicate. For brokers and investors alike, this episode offers a clear, tactical playbook for thriving in a rapidly evolving insurance landscape. 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
March 31 · 28 min
Beyond Postcodes: Mapping True Exposure | Nick Franz of Altitude Intelligence
In this episode of Making Risk Flow: Exploring the Ecosystem, host Jake Harding speaks with Nick Franz, founder of Altitude Intelligence, on why traditional underwriting data can obscure true risk exposure. Due to his background in intelligence, Nick has asked that we protect his identity. Nick shares how geospatial and spatial intelligence, rooted in military tradecraft, can transform insurance decision-making. They explore why risk must be understood as a dynamic system, not a static label, and how embedding context at data ingestion enables faster, more accurate underwriting. From identifying hidden dependencies to avoiding outdated datasets, the conversation reveals how leading insurers are building a durable competitive edge. The takeaway is clear: those who integrate intelligence-driven insights today will outperform, while others risk compounding losses and blind spots. 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
March 24 · 41 min
Automating Risk Workflows End-to-End to Eliminate Friction | Sam Lewis of Cytora
In this episode of Making Risk Flow: Exploring the Ecosystem, host Juan de Castro speaks with Sam Lewis, VP of Product, Engineering, and Data at Cytora, about how agentic AI is reshaping insurance workflows. They explore the shift from manual, fragmented processes to seamless, stateful systems that use memory and context to manage end-to-end submissions. Sam explains why the real barrier to digitization has been behavioral, not technical, and how designing for zero workflow disruption drives adoption among brokers. The conversation unpacks how AI agents increase underwriting capacity, improve responsiveness, and enable more consistent risk selection. They also discuss routing submissions intelligently, closing data gaps through enrichment, and freeing underwriters to focus on judgment-based decisions. The result is a more scalable, efficient, and accessible insurance ecosystem powered by always-on automation and intelligent orchestration. 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