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.

Fan Mail: Got a challenge digitizing your intake? Share it with us, and we’ll unpack solutions from our experience at Cytora.

To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'.

Our previous guests include: Bronek Masojada of PPL, Craig Knightly of Inigo, Andrew Horton of QBE Insurance, Simon McGinn of Allianz, Stephane Flaquet of Hiscox, Matthew Grant of InsTech, Paul Brand of Convex, Paolo Cuomo of Gallagher Re, and Thierry Daucourt of AXA.

Check out the three most downloaded episodes:

• The Five Pillars of Data Analytics Strategy in Insurance | Craig Knightly, Inigo
• 20 Years as CEO of Hiscox: Personal Reflections and the Evolution of PPL | Bronek Masojada
• Implementing ESG in the Insurance and Underwriting Space | Simon Tighe, Chaucer, and Paul McCarney, Moody's

In this episode of Making Risk Flow: 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.

Fan Mail: Got a challenge digitizing your intake? Share it with us, and we’ll unpack solutions from our experience at Cytora.

To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'.

Our previous guests include: Bronek Masojada of PPL, Craig Knightly of Inigo, Andrew Horton of QBE Insurance, Simon McGinn of Allianz, Stephane Flaquet of Hiscox, Matthew Grant of InsTech, Paul Brand of Convex, Paolo Cuomo of Gallagher Re, and Thierry Daucourt of AXA.

Check out the three most downloaded episodes:

• The Five Pillars of Data Analytics Strategy in Insurance | Craig Knightly, Inigo
• 20 Years as CEO of Hiscox: Personal Reflections and the Evolution of PPL | Bronek Masojada
• Implementing ESG in the Insurance and Underwriting Space | Simon Tighe, Chaucer, and Paul McCarney, Moody's

In this episode of Making Risk Flow, 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.

Fan Mail: Got a challenge digitizing your intake? Share it with us, and we’ll unpack solutions from our experience at Cytora.

To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'.

Our previous guests include: Bronek Masojada of PPL, Craig Knightly of Inigo, Andrew Horton of QBE Insurance, Simon McGinn of Allianz, Stephane Flaquet of Hiscox, Matthew Grant of InsTech, Paul Brand of Convex, Paolo Cuomo of Gallagher Re, and Thierry Daucourt of AXA.

Check out the three most downloaded episodes:

• The Five Pillars of Data Analytics Strategy in Insurance | Craig Knightly, Inigo
• 20 Years as CEO of Hiscox: Personal Reflections and the Evolution of PPL | Bronek Masojada
• Implementing ESG in the Insurance and Underwriting Space | Simon Tighe, Chaucer, and Paul McCarney, Moody's

In this episode of Making Risk Flow: 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. 

Fan Mail: Got a challenge digitizing your intake? Share it with us, and we’ll unpack solutions from our experience at Cytora.

To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'.

Our previous guests include: Bronek Masojada of PPL, Craig Knightly of Inigo, Andrew Horton of QBE Insurance, Simon McGinn of Allianz, Stephane Flaquet of Hiscox, Matthew Grant of InsTech, Paul Brand of Convex, Paolo Cuomo of Gallagher Re, and Thierry Daucourt of AXA.

Check out the three most downloaded episodes:

• The Five Pillars of Data Analytics Strategy in Insurance | Craig Knightly, Inigo
• 20 Years as CEO of Hiscox: Personal Reflections and the Evolution of PPL | Bronek Masojada
• Implementing ESG in the Insurance and Underwriting Space | Simon Tighe, Chaucer, and Paul McCarney, Moody's

In this episode of Making Risk Flow: 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. 

Fan Mail: Got a challenge digitizing your intake? Share it with us, and we’ll unpack solutions from our experience at Cytora.

To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'.

Our previous guests include: Bronek Masojada of PPL, Craig Knightly of Inigo, Andrew Horton of QBE Insurance, Simon McGinn of Allianz, Stephane Flaquet of Hiscox, Matthew Grant of InsTech, Paul Brand of Convex, Paolo Cuomo of Gallagher Re, and Thierry Daucourt of AXA.

Check out the three most downloaded episodes:

• The Five Pillars of Data Analytics Strategy in Insurance | Craig Knightly, Inigo
• 20 Years as CEO of Hiscox: Personal Reflections and the Evolution of PPL | Bronek Masojada
• Implementing ESG in the Insurance and Underwriting Space | Simon Tighe, Chaucer, and Paul McCarney, Moody's

In this episode of Making Risk Flow, host Juan de Castro 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.

Fan Mail: Got a challenge digitizing your intake? Share it with us, and we’ll unpack solutions from our experience at Cytora.

To receive a custom demo from Cytora, click here and use the code 'Making Risk Flow'.

Our previous guests include: Bronek Masojada of PPL, Craig Knightly of Inigo, Andrew Horton of QBE Insurance, Simon McGinn of Allianz, Stephane Flaquet of Hiscox, Matthew Grant of InsTech, Paul Brand of Convex, Paolo Cuomo of Gallagher Re, and Thierry Daucourt of AXA.

Check out the three most downloaded episodes:

• The Five Pillars of Data Analytics Strategy in Insurance | Craig Knightly, Inigo
• 20 Years as CEO of Hiscox: Personal Reflections and the Evolution of PPL | Bronek Masojada
• Implementing ESG in the Insurance and Underwriting Space | Simon Tighe, Chaucer, and Paul McCarney, Moody's

In this episode of Making Risk Flow, host Jake Harding 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.

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

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.

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

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.

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

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.

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