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 conver...
May 19, 2026•40 min•Season 8Ep. 18
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 tech...
May 12, 2026•35 min•Season 8Ep. 17
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 underwr...
May 05, 2026•44 min•Season 8Ep. 16
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 of...
Apr 28, 2026•32 min•Season 8Ep. 15
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 implementat...
Apr 21, 2026•46 min•Season 8Ep. 14
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...
Apr 14, 2026•41 min•Season 8Ep. 13
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...
Apr 07, 2026•37 min•Season 8Ep. 12
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, ...
Mar 31, 2026•28 min•Season 8Ep. 11
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...
Mar 24, 2026•42 min•Season 8Ep. 10
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, includi...
Mar 17, 2026•24 min•Season 8Ep. 9
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 reinforc...
Mar 10, 2026•39 min•Season 8Ep. 8
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 exp...
Mar 03, 2026•41 min•Season 8Ep. 7
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 t...
Feb 24, 2026•40 min•Season 8Ep. 6
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 ind...
Feb 17, 2026•34 min•Season 8Ep. 5
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...
Feb 10, 2026•24 min•Season 8Ep. 4
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 ac...
Feb 03, 2026•35 min•Season 8Ep. 3
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...
Jan 27, 2026•26 min•Season 8Ep. 2
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 conversati...
Jan 20, 2026•40 min•Season 8Ep. 1
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, an...
Jan 13, 2026•24 min•Season 7Ep. 16
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 ...
Dec 23, 2025•31 min•Season 7Ep. 15
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 journ...
Dec 16, 2025•56 min•Season 7Ep. 14
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...
Dec 09, 2025•28 min•Season 7Ep. 13
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 ...
Dec 02, 2025•31 min•Season 7Ep. 12
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. D...
Nov 25, 2025•28 min•Season 7Ep. 11
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 stat...
Nov 18, 2025•29 min•Season 7Ep. 10
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 partners...
Nov 11, 2025•31 min•Season 7Ep. 9
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, witho...
Nov 06, 2025•13 min•Season 7Ep. 8
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 Analyze...
Oct 28, 2025•29 min•Season 7Ep. 7
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 connecte...
Oct 14, 2025•33 min•Season 7Ep. 6
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...
Sep 30, 2025•17 min•Season 7Ep. 5
