Explore every episode of the podcast Making Risk Flow | The Future of Insurance
| Title | Pub. Date | Duration | |
|---|---|---|---|
| The Future of Insurance is Submissionless | Five Industry Leaders Explain Why | 06 Oct 2026 | 00:19:00 | |
Insurance is becoming more complex, but the way the industry works doesn’t have to be. In this compilation episode of Making Risk Flow, Juan de Castro and Jake Harding bring together insights from Luke Bills of Liberty Mutual, Patrick Meehan of Dun & Bradstreet, Simon de la Hoyde and Mark Varley of AddressCloud, and Ann Haugh of AXIS Capital to explore how technology can remove friction across the insurance value chain. To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'. | |||
| Stop Automating Broken Workflows: Insurers Need a New Operating Model, Not Another Tool | Patrick Meehan, Dun & Bradstreet | 29 Sep 2026 | 00:33:54 | |
What if the biggest opportunity for insurance AI isn't better automation, but better data? In this episode of Making Risk Flow, host Jake Harding sits down with Patrick Meehan, Senior Solution Director at Dun & Bradstreet UK – Insurance Services, to explore why trusted business data, entity resolution, and continuous monitoring are becoming critical to the future of commercial insurance. They discuss why insurers need to move beyond fragmented, policy-by-policy snapshots toward a shared view of the customer across underwriting, claims, compliance, and renewal. Patrick also explores the hidden concentration risks within seemingly diversified portfolios, the challenges of building and maintaining data infrastructure at scale, and why insurers should start with measurable business problems rather than massive enterprise data projects. Tune in to discover how connected data can reduce duplication, improve risk visibility, and help insurers build workflows designed for AI. To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'. | |||
| The Hidden Cost of Scale in Insurance Brokerage - and What Carriers Really Want from AI | Igno van Waesberghe, Aquiline | 22 Sep 2026 | 00:42:14 | |
What if the future of insurance isn't about bigger consolidation, but smarter specialization? In this episode of Making Risk Flow, host Juan de Castro sits down with Igno van Waesberghe, Managing Partner at Aquiline, to explore why MGAs and specialized brokers are reshaping the industry, how AI is fundamentally changing personal lines distribution, and the key strategies that separate durable insurance businesses from the rest. Packed with candid insights on broker consolidation across the Atlantic, the rise of alternative capital, and where real value is being captured in AI-enabled platforms, this conversation cuts through the hype to reveal what actually drives success in modern insurance. Tune in to discover why specialization, talent alignment, and technology integration are the real competitive advantages reshaping insurance today. To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'. | |||
| The Rekeying Trap: Why Insurance Needs to Stop Making Agents Do the Same Work Twice | Luke Bills | 15 Sep 2026 | 00:30:24 | |
What if you could eliminate the tedious data rekeying that eats up agents' days and instead focus on what truly matters: understanding risk and serving clients? In this episode of Making Risk Flow, host Juan de Castro sits down with Luke Bills, President of Independent Agent Distribution at Liberty Mutual, to explore how AI and automation can remove friction from insurance workflows. They discuss how technologies such as email-to-quote, API-driven processes, and SubmissionLess can eliminate repetitive data rekeying and streamline risk submissions. Luke explains why insurers should decouple intake channels from underwriting processes and use risk complexity, not premium size alone, to determine how submissions are handled. The conversation also explores how AI can amplify the value of independent agents by freeing them to focus on risk management, client relationships, and growth. Finally, Juan and Luke examine the importance of responsible AI governance, including model validation, privacy, human oversight, and cross-functional collaboration, when deploying AI across the insurance industry. To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'. | |||
| [Greatest Hits] The Iteration Trap: Why 'Improving' Your Underwriting is Killing Your Growth | Bryan Falchuk | 08 Sep 2026 | 00:45:55 | |
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. To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'. | |||
| The Agile Insurer: How AI, People and Strategy Are Reshaping Insurance | 8 Industry Leaders | 25 Aug 2026 | 00:18:38 | |
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. To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'. | |||
| [Greatest Hits] From Relevance to Resilience: Inside the Evolution of Modern Insurance | Jean-Jacques Henchoz | 18 Aug 2026 | 00:28:18 | |
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. To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'. | |||
| Beyond Risk Scores: The New Intelligence Driving Insurance Underwriting | 10 Industry Leaders | 11 Aug 2026 | 00:21:29 | |
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. To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'. | |||
| [Greatest Hits] Re-Architecting Insurance for Speed, Data and Resilience | David McMillan, Jensten | 04 Aug 2026 | 00:39:31 | |
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. To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'. | |||
| Why Operations Is the Ultimate Growth Engine in Insurance | Ann Haugh | 29 Jul 2026 | 00:37:33 | |
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. To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'. | |||
| [Greatest Hits] The Speed Advantage: How AI and Customer Obsession Are Reshaping Specialty Insurance | Christian Stobbs | 21 Jul 2026 | 00:40:00 | |
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. To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'. | |||
| Why Better Data Helps Underwriters Say 'Yes' More Often | Mark Varley & Simon de la Hoyde | 14 Jul 2026 | 00:34:29 | |
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. To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'. | |||
| Beyond Automation: The Real Drivers of Underwriting Transformation | Allison Hamilton | 09 Jul 2026 | 00:33:17 | |
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. To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'. | |||
| Property Intelligence at Scale: How Geospatial Data Is Redefining Insurance Underwriting | Izik Lavy and Jacob Grob | 30 Jun 2026 | 00:39:26 | |
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. To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'. | |||
| Think Slow, Execute Fast: The New Playbook for Vertical AI Transformation in Insurance | Kristoffer Lundberg | 23 Jun 2026 | 00:32:18 | |
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. To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'. | |||
| Lead, Follow, or Fall Behind? Positioning for Success in the Insurance Market | Greg Brown | 16 Jun 2026 | 00:41:10 | |
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. To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'. | |||
| Beyond Traffic-Light Risk Scores: Building Climate Risk Models That Actually Work | Joan Saladich (Part 2) | 09 Jun 2026 | 00:29:52 | |
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. To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'. | |||
| Beyond Traffic-Light Risk Scores: Building Climate Risk Models That Actually Work | Joan Saladich (Part 1) | 02 Jun 2026 | 00:26:02 | |
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. To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'. | |||
| Why Climate Data is Forming the Risk Intelligence Blueprint for Commercial Insurance | Caroline Grey | 26 May 2026 | 00:35:08 | |
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. To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'. | |||
| The Speed Advantage: How AI and Customer Obsession Are Reshaping Specialty Insurance | Christian Stobbs | 19 May 2026 | 00:40:00 | |
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. To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'. | |||
| Making Risk Flow Special Edition | 5 Insurance Leaders on Winning the AI Transformation Race | 12 May 2026 | 00:35:00 | |
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. To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'. | |||
| Risk, Reimagined: 11 Experts on Turning Data into Decisions | 05 May 2026 | 00:44:12 | |
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. To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'. | |||
| The Real-Time Data Edge: Why Speed and Accuracy Beat Volume in Underwriting | Pierre-Henri Janssens | 28 Apr 2026 | 00:32:18 | |
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. To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'. | |||
| The Iteration Trap: Why 'Improving' Your Underwriting is Killing Your Growth | Bryan Falchuk | 21 Apr 2026 | 00:45:55 | |
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. To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'. | |||
| Beyond CVSS: The New Cyber Underwriting Playbook | Jay Wallace of VulnCheck | 14 Apr 2026 | 00:40:33 | |
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. To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'. | |||
| The Broker Edge in an AI-Driven Insurance Market | Nicolas Zerbib of Stonepoint Capital | 07 Apr 2026 | 00:37:24 | |
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. To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'. | |||
| Beyond Postcodes: Mapping True Exposure | Nick Franz of Altitude Intelligence | 31 Mar 2026 | 00:28:13 | |
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. To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'. | |||
| Automating Risk Workflows End-to-End to Eliminate Friction | Sam Lewis of Cytora | 24 Mar 2026 | 00:41:57 | |
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. To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'. | |||
| Most Property Data Is Wrong. Here’s What That Means for Insurers | Jon Francis of Chimnie | 17 Mar 2026 | 00:23:38 | |
In this episode of Making Risk Flow: Exploring the Ecosystem, host Jake Harding speaks with Jon Francis, Chief Product Officer at Chimnie, about why the future of property insurance underwriting depends on transparent, high-quality data. Jon explains how flawed or overly averaged property data can distort rebuild cost models, misprice risk, and ultimately drive adverse selection across insurance portfolios. He outlines practical methods for validating external data providers at scale, including large-volume testing to uncover hidden discrepancies that vendor samples often miss. The conversation also introduces a structured approach for transitioning to more accurate data systems while maintaining internal trust and regulatory confidence. From uncovering edge-case property characteristics to enabling frictionless quote journeys, Jon shows how granular property intelligence can become a powerful competitive advantage for insurers willing to modernize their risk data infrastructure. To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'. | |||
| AI, Agents, and the Power of Connection in Insurance | Bill Harris & Drake Slaikeu-Lawhead of ITC Vegas | 10 Mar 2026 | 00:39:15 | |
In this episode of Making Risk Flow, host Juan de Castro speaks with Bill Harris and Drake Slaikeu-Lawhead of ITC Vegas about how insurance growth hinges less on tools and more on connection. They explore how Insurtech Connect’s “neighbourhood” model helps carriers, brokers, and agents navigate 700+ vendors by organising solutions around real business needs. The conversation dives into AI’s impact on distribution, streamlining ACORD processing, claims, and upstream risk transfer, while reinforcing that independent agents remain essential for trust-based advice. As pilots shrink from years to months, speed to impact becomes the new competitive edge. Yet in a digital-first era, they argue that face-to-face interaction still drives the most valuable outcomes. Serendipity, not just software, is what truly keeps risk flowing. To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'. | |||
| Adapt or Fall Behind: Why Cultural Evolution Equals Competitive Edge | Bryan Falchuk | 03 Mar 2026 | 00:41:20 | |
In this 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. To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'. | |||
| Re-Architecting Insurance for Speed, Data and Resilience | David McMillan, Jensten | 24 Feb 2026 | 00:39:31 | |
In this episode of Making Risk Flow, host Juan de Castro speaks 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. To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'. | |||
| Finding the 20–40% Your Portfolio Is Missing | Greg Johnson & John Petricelli, Confianza | 17 Feb 2026 | 00:34:14 | |
In this episode of Making Risk Flow: Exploring the Ecosystem, host Jake Harding speaks with Greg Johnson, CEO of Confianza, and Chief Data Officer John Petricelli about the hidden profitability most carriers overlook. They explore how legacy data strategies leave 20–40% of premium and portfolio value untapped, and why context-driven, niche data sources are reshaping underwriting and renewals. From tenant risk and household composition to commodity-linked replacement costs and behavioural indicators, Greg and John explain how richer inputs create sharper risk selection and pricing accuracy. The conversation also highlights portfolio optimisation as a powerful growth lever, identifying leakage, misclassified exposures, and cross-sell opportunities already within the book. It’s a practical discussion on engineering discipline in analytics and building a 360-degree view of risk to unlock measurable competitive advantage. To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'. | |||
| Making Risk Flow Across the Insurance Value Chain | Richard Hartley, Cytora (Applied Systems) | 10 Feb 2026 | 00:23:48 | |
In this episode of Making Risk Flow, recorded live at the ITC London 2026 event, host Juan de Castro speaks with Richard Hartley, CEO and Founder of Cytora (now part of Applied Systems), about what it really takes to digitize risk across the entire insurance value chain. They explore why transformation fails when insurers focus on isolated workflows instead of interconnected pain points across agents, brokers, and carriers. Richard breaks down how agentic AI is reshaping underwriting, why risk data must be treated as dynamic rather than static, and how channel-agnostic operating models unlock scale. The conversation offers practical insights on automation, buy-vs-build decisions, and what risk digitization will demand in 2026. To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'. | |||
| Unlocking Hidden Opportunities in Advanced Climate Modelling | Dave Wood, JBA Risk Management | 03 Feb 2026 | 00:34:34 | |
In this episode of Making Risk Flow: Exploring the Ecosystem, host Jake Harding speaks with Dave Wood, Managing Director at JBA Risk Management, about how AI and deep learning are reshaping catastrophe risk modeling. Dave explains how neural networks can simulate extreme climate scenarios that fall outside historical records, helping insurers better understand compound and tail risks. The conversation also explores why model transparency and rigorous validation are essential as AI adoption accelerates, and how insurers can scale advanced weather simulation without sacrificing accuracy. Dave also shares practical guidance on integrating best-in-class AI tools into existing risk platforms, rather than building everything from scratch in-house. To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'. | |||
| How Precision Climate Data Is Rewriting Insurance Risk Pricing | Duško Radulović, Climatig | 27 Jan 2026 | 00:26:17 | |
In this episode of Making Risk Flow: Exploring the Ecosystem, host Jake Harding speaks with Duško Radulović, Founder and CEO of Climatig, about how high-resolution climate intelligence is reshaping insurance underwriting and portfolio strategy. Duško explains why moving beyond regional averages to meter-level precision allows insurers to identify true physical risk and price policies more accurately and reduce loss volatility. The conversation explores how machine learning fills critical data gaps for perils like hail and landslides, why climate forecasts must align with policy durations rather than long-term averages, and how transparency and validation build trust in predictive models. The episode offers practical insights into using data-driven climate risk assessment as a competitive advantage for underwriters, MGAs, and portfolio managers. To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'. | |||
| Why Operating Model Beats Portfolio Strategy in Insurance | Antonio Grimaldi, McKinsey | 20 Jan 2026 | 00:39:42 | |
In this episode of Making Risk Flow, host Juan de Castro speaks with Antonio Grimaldi, Partner at McKinsey, about how London Market carriers can unlock growth by redesigning their operating models, not just optimising portfolios. They explore why execution drives the majority of performance, how underwriting workflows must be reimagined to free up judgement-led work, and what the shift towards facilities, MGAs, and alternative distribution means for competitive differentiation. The conversation cuts through the AI hype, outlining a pragmatic buy-versus-build framework and the real cost of “POC purgatory”. Antonio also reframes relationship-based service for 2026, arguing that speed, clarity, and decisive underwriting strengthen broker relationships more than manual processes; especially in a softening market. To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'. | |||
| Why Claims Accuracy Is Insurance’s Biggest ROI Lever | Evgeny Aleksandrov, PilotBird | 13 Jan 2026 | 00:23:54 | |
In this episode of Making Risk Flow, host Jake Harding speaks with Evgeny Aleksandrov, Founder and CEO of PilotBird, about why claims accuracy, and not speed, is the biggest lever in modern insurance. Evgeny explains how open-source intelligence and lifestyle analytics help insurers validate claims earlier, uncover organised fraud networks, and avoid costly post-payout recovery. The conversation explores how curated data can mislead adjusters, why a “trust and verify” approach is essential, and how early-lifecycle intelligence delivers outsized returns, often 14–56x ROI. They also discuss how better data tools improve adjuster satisfaction and retention, and what insurers must do to responsibly adopt emerging data sources at scale to future-proof their risk infrastructure. To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'. | |||
| Top Episodes of 2025: The Hartford’s Next Chapter: Building a Global Insurance Powerhouse | Carl Bach, The Hartford | 23 Dec 2025 | 00:30:42 | |
Welcome to a special end-of-the-year series on Making Risk Flow as we count down the weeks to the end of 2025. The series is a collection of our top episodes from this year. Each Tuesday, we will re-release one standout episode as we build up to releasing our top fan favourite on the last Tuesday. In this episode replay, host Juan de Castro sits down with Carl Bach, CEO of Hartford Underwriting Agency, about how a 200-year-old insurer is modernising for the future. They discuss Hartford’s brand refresh, maintaining its historic stag emblem while evolving its global identity. Carl outlines the company’s strategic transformation since 2019, which is focused on streamlining operations and ramping up specialisation in marine, energy, and financial lines. The conversation also covers Hartford’s international growth ambitions through Lloyd’s syndicate 1221, its approach to serving diverse market segments, and its use of AI and intelligent document processing in underwriting. Carl shares insights on balancing tradition with innovation, underscoring Hartford’s values, especially "own it with pace," as the company embraces change and seizes new opportunities in a fast-evolving industry. To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'. | |||
| Top Episodes of 2025: The Vertical Advantage: How Specialisation Drove Success in Insurance | Marcus Ryu, Guidewire | 16 Dec 2025 | 00:55:47 | |
Welcome to a special end-of-the-year series on Making Risk Flow as we count down the weeks to the end of 2025. The series is a collection of our top episodes from this year based on views, downloads, and overall engagement. Each Tuesday, we will re-release one standout episode as we build up to releasing our top fan favourite on the last Tuesday. In this episode, host Juan de Castro sits down with Marcus Ryu, former CEO and current strategic adviser at Guidewire Software. Marcus shares his journey from management consulting to co-founding one of the leading software providers for the property and casualty insurance industry. He offers candid insights into the trials and triumphs of entrepreneurship, including pivotal moments such as navigating a competitive lawsuit and transitioning to the public markets. A central aspect of Marcus's story is Guidewire’s contrarian belief in the power of vertical solutions. By developing mission-critical software tailored to the specific needs of the P&C insurance sector, Guidewire revolutionized how insurers manage claims, policies, and billing. Now a partner at Battery Ventures, Marcus discusses how his experiences at Guidewire inform his approach to investing in the next generation of startups. From the importance of customer-centricity to leveraging technology to solve real-world problems, this conversation is packed with actionable insights for founders and industry professionals alike. Whether you're revisiting the episode or viewing it for the first time, this episode offers tactical guidance for actionable insights for founders and industry professionals alike. To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'. | |||
| Top Episodes of 2025: Practitioner’s Guide: The Blueprint for Risk Digitization POCs | Zaheer Hooda and Richard Lewis, Cytora | 09 Dec 2025 | 00:28:24 | |
Welcome to a special end-of-the-year series on Making Risk Flow as we count down the weeks to the end of 2025. Each Tuesday, we will re-release one standout episode as we build up to releasing our top fan favourite on the last Tuesday. In this episode, Juan de Castro is joined by his colleagues, Rich Lewis, Cytora's Sales Director, and Zaheer Hooda, Head of North America, for a deep dive into what makes proof-of-concept (POC) initiatives in risk digitisation succeed or fail. Drawing on firsthand experience from working with leading carriers, they break down five essential capabilities insurers need to get right when implementing digitisation initiatives, from extraction accuracy and full-spectrum intake handling to scalable deployment and human-in-the-loop exception management. They also provide a practical, inside look at how insurers structure effective proof of concept processes, including live workshops, data preparation, success metrics, and how to align POC design with measurable business outcomes. Whether you're revisiting the episode or viewing it for the first time, this episode offers tactical guidance to ensure your technology investments deliver meaningful impact. To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'. | |||
| From Hype to Hard ROI: Making AI Actually Work in Insurance | Matthew Grant, InsTech | 02 Dec 2025 | 00:31:25 | |
In this episode of Making Risk Flow, host Jake Harding speaks with Matthew Grant, founder and CEO of Instech and a veteran of 33 years in catastrophe modelling. Matthew unpacks why insurance’s cautious approach to AI is more strategic than sceptical. Together, they explore how carriers can align technology adoption with real business problems, build trust in new data sources, and drive operational efficiency without disrupting core workflows. Matthew explains why consistency in user interfaces can mask major capability leaps, how to focus on outcomes rather than perfection in data quality, and why the industry’s measured pace reflects deep risk intelligence. The conversation offers insurers a clear roadmap on how a purposeful adoption of AI and cultural innovation can drive a durable competitive advantage. To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'. | |||
| Making Risk Flow – Season 7 Highlights | Top Lessons & Expert Takeaways | 25 Nov 2025 | 00:27:47 | |
In this special compilation episode of Making Risk Flow, host Juan de Castro revisits conversations with the industry leaders who shaped Season 7. Join Allison Thornicroft, Yaemish Rughoo, Mark Allan, Greg Hendrick, Bilge Mert, Jean-Jacques Henchoz, and Lambros Lambrou to explore why speed and efficiency matter in commercial insurance, how AI and technology are reshaping underwriting workflows, and the key strategies insurers are using to standardize processes and drive real value for clients. To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'. | |||
| Exploring the Ecosystem: From Reactive to Predictive: The Proactive Advantage Reshaping Cyber Insurance Today | 18 Nov 2025 | 00:28:48 | |
In this episode of Making Risk Flow, host Jake Harding speaks with Ross Wirth, Head of Strategic Tech Ecosystem at CyberCube, about why cyber insurance requires a new playbook for risk assessment. Ross explains how traditional underwriting struggles to keep pace with dynamic security environments, and why real-time data visibility is now essential for identifying concentration risk, single points of failure, and systemic exposures like cloud outages. The conversation explores shifting from static applications to continuous monitoring, balancing AI-driven insights with human judgment, and designing underwriting strategies that prioritise prevention over post-incident repair. Whether you're an underwriter, broker, or cyber risk leader, this episode offers practical guidance on using data intelligently while preserving the relationship-driven core of insurance. To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'. | |||
| Fast, Data-Driven Decisions and the Future of Risk | Mark Allan, Ki Insurance | 11 Nov 2025 | 00:30:34 | |
In this episode of Making Risk Flow, Juan de Castro sits down with Mark Allan, CEO of Ki Insurance, to explore how a digital-first, data-led approach is transforming underwriting in the London market. Mark shares how Ki combines algorithmic precision with human expertise to underwrite individual risks at unprecedented speed, while maintaining portfolio-level oversight. This episode explores Ki’s mission-driven culture, the challenges of blending technology and insurance talent, and how partnerships with brokers and carriers are amplifying the impact of their platform. From building a billion-dollar business to enabling a more seamless, data-driven flow of risk, Mark explains how Ki is reshaping the ecosystem and setting a new standard for efficiency, collaboration, and innovation in insurance. To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'. | |||
| Exploring the Ecosystem: How Relativity6 Is Powering AI That Works | Alan Ringvald, Relativity6 | 06 Nov 2025 | 00:13:22 | |
Welcome to a new episode of Making Risk Flow: Exploring the Ecosystem. Our host Jake Harding welcomes Alan Ringvald, CEO and co-founder of Relativity6, to unpack how AI and multi-source data are redefining underwriting. Together, they explore why insurers must move beyond generic AI tools toward workflow-specific solutions that integrate seamlessly into real underwriting environments. Alan shares how intelligent data aggregation can empower underwriters with trusted, actionable insights, without adding complexity, and why automation is now essential to handle rising submission volumes profitably. The conversation highlights a future where AI enhances, rather than replaces, human judgment, creating a true partnership between people and machines. Discover how early adopters of intelligent automation will lead the next era of efficient, insight-driven insurance. To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'. | |||
| Turning Risk into Opportunity: Inside Aon’s Data-Driven Approach | Lambros Lambrou, Aon | 28 Oct 2025 | 00:28:56 | |
In this episode of Making Risk Flow, host Juan de Castro welcomes Lambros Lambrou, Chief Strategy Officer at Aon, to explore how one of the world’s largest insurance brokers is transforming risk management through data, AI, and innovation. They discuss how global megatrends, trade, technology, weather, and workforce are reshaping the insurance landscape and why a shift from traditional risk protection to enabling upside growth is crucial. Lambrou explains how Aon’s “One Data Lake,” Risk Analyzers, and Broker Copilot tools provide real-time, predictive insights that help clients make smarter decisions across property, casualty, cyber, and health insurance. The conversation highlights the importance of breaking down silos, aligning teams around client outcomes, and leveraging technology to deliver integrated, intelligent risk solutions worldwide. To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'. | |||
| Maximising Hero Work: How AI is Transforming Commercial Insurance | Graham Blackwell, Applied Systems | 14 Oct 2025 | 00:33:21 | |
In this episode of Making Risk Flow, host Juan de Castro welcomes Graham Blackwell, President of Applied Systems, to explore the transformative power of technology in insurance. They discuss how Applied Systems and Cytora are joining forces to streamline workflows, reduce manual processes, and enhance collaboration between brokers and carriers. From reimagining commercial submissions to maximising “hero work,” Graham shares insights on leveraging AI to create a seamless, efficient, and connected insurance ecosystem. Discover how Applied Systems evolved into a market leader, the role of AI in eliminating mundane tasks, and the strategic vision for integrating agency workflows, carrier connectivity, and automation to accelerate insurance processes and empower professionals across the industry. To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'. | |||
| From Data to Decision | The AI-Driven Revolution in Commercial Underwriting | 30 Sep 2025 | 00:17:24 | |
In this special compilation episode of Making Risk Flow, host Juan de Castro revisits our conversations with industry leaders Carl Bach, Johan Slabbert, Bettina Dietsche, Cassandra Vukorep, and others to explore how digital transformation and AI are revolutionising the commercial insurance sector. This episode provides a discussion on efficient operating models, integrating external and historical data for better risk assessment, and balancing automation with human expertise. Our featured guests share insights on scaling AI adoption, building future-ready teams, and tackling the complexities of data standardisation. With a focus on practical implementation and change leadership, this episode offers valuable guidance for insurance professionals navigating the evolving landscape of risk, technology, and human capital. To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'. | |||
| From Relevance to Resilience: Inside the Evolution of Modern Insurance | Jean-Jacques Henchoz, Brit Insurance | 16 Sep 2025 | 00:28:18 | |
In this 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. To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'. | |||