Cyber Insurance Leaders

Hollywood sells cyber apocalypse. The data tells a different story.For years, cyber war has been framed as the systemic threat that could destabilize the insurance market overnight. But does the evidence support that assumption, or are we pricing a risk that hasn’t materialized at the scale we fear?In this episode, host Anthony Hess speaks with Tom Johansmeyer, Global Head of Index Classes at Price Forbes Re, and a doctoral researcher examining the intersection of insurance, economic security, and cyber conflict.Drawing on case studies from NotPetya to large-scale infrastructure outages, Tom challenges how the industry thinks about cyber war exclusions, systemic cyber risk, and catastrophe benchmarks. He argues that many feared scenarios are either bounded in scale or comparable to natural catastrophe events the market already absorbs.If that’s true, what does it mean for capital allocation, reinsurance structures, quota shares, and pricing discipline? This episode reframes the debate around systemic cyber risk, and explores what a more rational, scalable cyber insurance market could look like.You’ll learn:1. Why systemic cyber war risk may be overstated2. How NotPetya reshaped underwriting psychology3. What catastrophe benchmarks reveal about cyber scale4. How fear impacts capital and reinsurance strategy5. What a healthier cyber insurance market could look like___________Get in touch with Tom Johansmeyer on LinkedIn: https://www.linkedin.com/in/tjohansmeyer/___________About the host Anthony Hess:Anthony is passionate about cyber insurance. He is the CEO of Asceris, which supports clients to respond to cyber incidents quickly and effectively. Originally from the US, Anthony now lives in Europe with his wife and two children.Get in touch with Anthony on LinkedIn: https://www.linkedin.com/in/anthonyhess/ or email: [email protected].___________Thanks to our friends at SAWOO for producing this episode with us!

In incident response, if you wipe systems first and ask questions later, you’re deleting the truth.In this episode, host Anthony Hess sits down with Devon Ackerman, Global Head of Digital Forensics and Incident Response at Cybereason, to unpack what serious DFIR looks like when your audience is regulators, legal counsel, and insurance carriers and brokers. A former FBI Supervisory Special Agent and Senior Forensic Examiner, Devon explains why his team approaches every matter as if it could end up in court, and what that changes in practice.He breaks down how to scope an incident from the first call, preserve evidence before “fixing” the environment, and pressure-test tool output instead of blindly trusting it. Anthony and Devon also dig into AI and automation in DFIR, the central role of timelines and logging in telling a credible breach story, and why third- and fourth-party access, zero trust, and contracts are now defining systemic cyber risk for boards and insurers alike.You'll learn:1. Why “defensible truth” is the real product in high-stakes incident response2. How forensic-science DFIR changes scoping, evidence preservation, and decision-making3. Where AI speeds up investigations and where it creates blind spots for junior teams4. Why timelines and logging shape what carriers, regulators, and boards believe happened5. How vendor access and contracts drive third- and fourth-party cyber risk at scale___________Get in touch with Devon Ackerman on LinkedIn: https://www.linkedin.com/in/devonackerman/___________About the host Anthony Hess:Anthony is passionate about cyber insurance. He is the CEO of Asceris, which supports clients to respond to cyber incidents quickly and effectively. Originally from the US, Anthony now lives in Europe with his wife and two children.Get in touch with Anthony on LinkedIn: https://www.linkedin.com/in/anthonyhess/ or email: [email protected].___________Thanks to our friends at SAWOO for producing this episode with us!

During incident response, what separates good from great counsel is bedside manner.In this episode, host Anthony Hess sits down with Josh Mooney, Partner and US Head of Cyber and Data Privacy at Kennedys Law, for a candid look at effective cyber response leadership.Josh explains why empathy and communication are as critical as legal precision when guiding clients through chaos. He also shares how US courts are reshaping ransomware incentives, why data governance failures attract OCR scrutiny, and how privacy law is edging toward a fifth fundamental right, namely the right not to be tracked.From the psychology of crisis response to courtroom strategy and compliance realities, Josh reveals how the next decade of cyber risk will test not only systems, but the people behind them.You’ll learn:1. Why empathy and trust are strategic tools in breach response2. How US court rulings are driving ransom payment dilemmas3. What OCR investigations reveal about weak governance4. Why data inventory discipline determines breach outcomes5. How privacy law may soon expand to include a “right not to be tracked”___________Get in touch with Josh Mooney on LinkedIn: https://www.linkedin.com/in/joshua-mooney-cybersecurity/___________About the host Anthony Hess:Anthony is passionate about cyber insurance. He is the CEO of Asceris, which supports clients to respond to cyber incidents quickly and effectively. Originally from the US, Anthony now lives in Europe with his wife and two children.Get in touch with Anthony on LinkedIn: https://www.linkedin.com/in/anthonyhess/ or email: [email protected].___________Thanks to our friends at SAWOO for producing this episode with us!

Telemetry is changing the underwriting game, enabling a shift from clunky forms to real-time, verifiable risk data.In this episode, host Anthony Hess sits down with Alex Jomaa, Chief Underwriting Officer at Onda, to explore how real-time data is transforming cyber underwriting, and why it’s time the industry stopped relying on outdated processes that frustrate clients and slow brokers down.Alex explains how Onda’s Navigator platform integrates directly with a client’s infrastructure to deliver objective, verifiable cyber risk insights, thereby eliminating the back-and-forth of long-form questionnaires. In addition, he unpacks the biggest hurdles to cyber adoption, from poor timing and over-complication to misaligned incentives and volatile pricing cycles.You'll learn:1. How telemetry brings scale, accuracy, and speed to cyber underwriting2. What really stops buyers from purchasing cyber policies3. How brokers can sell cyber coverage more effectively4. The key signals Onda uses to assess cyber hygiene and risk quality5. Why market volatility is damaging long-term trust in cyber insurance___________Get in touch with Alex Jomaa on LinkedIn: https://www.linkedin.com/in/alex-jomaa-b84b8520/ ___________About the host Anthony Hess:Anthony is passionate about cyber insurance. He is the CEO of Asceris, which supports clients to respond to cyber incidents quickly and effectively. Originally from the US, Anthony now lives in Europe with his wife and two children.Get in touch with Anthony on LinkedIn: https://www.linkedin.com/in/anthonyhess/ or email: [email protected].___________Thanks to our friends at SAWOO for producing this episode with us!

When the market softened, Ridge didn’t follow the crowd. Here’s how discipline became their competitive edge. In this episode, host Anthony Hess sits down with Greg Markell, President & CEO at Ridge Canada Cyber Solutions Inc., for a candid conversation on what it takes to build a sustainable cyber MGA.Greg shares how Ridge has resisted the pull of chasing market share during soft cycles—maintaining its underwriting standards since 2020—and why he believes cyber risk transfer must be earned, not assumed. He unpacks Ridge’s strategy of building proprietary underwriting tools in-house, explains why AI is an efficiency enhancer (not a replacement for people), and introduces the company’s new “risk marketplace,” which helps brokers turn declines into actionable paths to coverage. You’ll learn:1. Why consistent underwriting is Ridge’s strategy for long-term profitability2. Why cyber coverage should depend on client maturity, not market capacity3. How Ridge balances internal tech and AI with human-led underwriting4. What Ridge’s “risk marketplace” offers when clients aren’t ready for coverage5. Why trusted vendor partnerships are core to a strong claims experience___________Get in touch with Greg Markell on LinkedIn: https://www.linkedin.com/in/gregmarkell/___________About the host Anthony Hess:Anthony is passionate about cyber insurance. He is the CEO of Asceris, which supports clients to respond to cyber incidents quickly and effectively. Originally from the US, Anthony now lives in Europe with his wife and two children.Get in touch with Anthony on LinkedIn: https://www.linkedin.com/in/anthonyhess/ or email: [email protected].___________Thanks to our friends at SAWOO for producing this episode with us!

What if the biggest threat to your cyber claims portfolio isn’t ransomware—but a spreadsheet buried in someone’s inbox?In this episode, host Anthony Hess chats with John Spiehs, Head of Claims at Converge, about what’s shifting in the cyber claims space—and what insurance professionals should have on their radar.John breaks down how Converge is leading efforts to simplify Business Interruption (BI) claims with a cleaner, more intuitive, top-down approach. He also digs into the growing exposure around data privacy, where even small incidents can trigger costly class actions. Finally, he explains what’s getting lost as the market softens, why vendor relationships matter more than price tags, and the kind of talent today’s claims teams really need.You'll learn:1. Why BI claims are evolving, and how Converge is simplifying the process2. Why data privacy and class actions are emerging as cyber’s new frontier3. Why soft market dynamics threaten underwriting discipline4. How poor email habits can explode breach costs overnight5. What defines a strong vendor partnership, beyond cut-rate solutions___________Get in touch with John Spiehs on LinkedIn: https://www.linkedin.com/in/john-s-b981337/___________About the host Anthony Hess:Anthony is passionate about cyber insurance. He is the CEO of Asceris, which supports clients to respond to cyber incidents quickly and effectively. Originally from the US, Anthony now lives in Europe with his wife and two children.Get in touch with Anthony on LinkedIn: https://www.linkedin.com/in/anthonyhess/ or email: [email protected].___________Thanks to our friends at SAWOO for producing this episode with us! 

Cyber insurers can’t just assess risk—they need to actively protect businesses from evolving threats.In this episode, host Anthony Hess welcomes Daniel Woods, Principal Security Researcher at Coalition, to explore how cyber insurers can move beyond risk transfer and take an active role in cybersecurity. Daniel explains how Coalition’s mission-driven approach sets it apart, and why active insurance has an edge in an era of escalating threats.You'll learn:1. Why cyber insurers must go beyond risk assessment and actively protect policyholders2. How web privacy litigation from the plaintiffs’ bar mirrors cybercriminal tactics3. The biggest blind spots in systemic cyber risk, and why a privacy casualty catastrophe is worth thinking about4. How insurers can build real-time risk mitigation into their coverage models5. The future of cyber insurance: Where the industry is headed and how insurers can stay ahead___________Get in touch with Daniel Woods on LinkedIn: https://www.linkedin.com/in/daniel-woods-82555199/___________About the host Anthony Hess:Anthony is passionate about cyber insurance. He is the CEO of Asceris, which supports clients to respond to cyber incidents quickly and effectively. Originally from the US, Anthony now lives in Europe with his wife and two children.Get in touch with Anthony on LinkedIn: https://www.linkedin.com/in/anthonyhess/ or email: [email protected].___________Thanks to our friends at SAWOO for producing this episode with us! 

Can your cyber insurance policy really deliver when it counts? Find out what separates a winning policy from a risky gamble.In this episode, host Anthony Hess welcomes David Anderson, Vice President of Cyber at Woodruff Sawyer, to explore the evolving cyber insurance landscape. David dives into the current trends shaping the market, sharing insights into what 2025 holds for privacy underwriting, ransomware risks, and premium stabilization. He reveals the common missteps that leave organizations vulnerable and offers actionable strategies to ensure your cyber insurance policy performs effectively in the event of a claim.You'll learn:1. Why privacy underwriting is the focal point of 2025 renewals2. How policy misalignment can lead to disastrous claims outcomes3. The must-have policy elements for manufacturing and tech firms4. Strategies to improve collaboration between CISOs and financial buyers5. Why underwriter scrutiny is shifting from quantity to efficacy of tools___________Get in touch with David Anderson on LinkedIn: https://www.linkedin.com/in/dava988/___________About the host Anthony Hess:Anthony is passionate about cyber insurance. He is the CEO of Asceris, which supports clients to respond to cyber incidents quickly and effectively. Originally from the US, Anthony now lives in Europe with his wife and two children.Get in touch with Anthony on LinkedIn: https://www.linkedin.com/in/anthonyhess/ or email: [email protected].___________Thanks to our friends at SAWOO for producing this episode with us! 

How can insurers, brokers, and clients all win through proactive risk management? Discover the strategies reshaping the cyber insurance ecosystem.In this episode, host Anthony Hess sits down with Sidd Gavirneni, Global Product Owner, Digital Risk Management at HSB. With a background spanning cybersecurity, entrepreneurship, and InsurTech innovation, Sidd shares his insights into transforming the cyber insurance landscape. He highlights how pre-breach services benefit insurers, brokers, and clients. This episode also explores personal cyber insurance, AI’s dual role in cybersecurity, and the value of partnerships in the cyber insurance ecosystem.You'll learn:1. Why pre-breach solutions are key to reducing claims and enhancing client trust2. How the insurance industry can unlock the potential of personal cyber coverage3. The challenges of data utilization in underwriting and ways to overcome them4. The role of AI as both a cybersecurity asset and a growing threat5. How closer collaboration between insurers and cybersecurity vendors drives innovation___________Get in touch with Sidd Gavirneni on LinkedIn: https://www.linkedin.com/in/siddgavirneni/___________About the host Anthony Hess:Anthony is passionate about cyber insurance. He is the CEO of Asceris, which supports clients to respond to cyber incidents quickly and effectively. Originally from the US, Anthony now lives in Europe with his wife and two children.Get in touch with Anthony on LinkedIn: https://www.linkedin.com/in/anthonyhess/ or email: [email protected].___________Thanks to our friends at SAWOO for producing this episode with us! 

In a market defined by uncertainty, is it possible to ever be ‘good’ at cyber insurance? Daniel Kasper thinks not—at least for now.In this episode, Daniel Kasper, CEO of QualRisk Cyber Insurance Center, joins host Anthony Hess to explore why the cyber insurance market is still in its infancy. Drawing from examples like the ransomware epidemic of 2019-2022, Daniel explains how the lack of historical systemic event data, a fast-evolving threat landscape, and inherent unpredictability make cyber insurance uniquely challenging.You'll learn:1. Why a standardized framework for cyber events could revolutionize the industry2. How to balance data-driven decisions with expert judgment in an imperfect market3. What makes cyber insurance uniquely difficult to master in today’s evolving landscape4. The consolidation wave reshaping the MGA sector and what it means for market players5. Why mastering cybersecurity fundamentals is essential for insurance professionals___________Get in touch with Daniel Kasper on LinkedIn: https://www.linkedin.com/in/daniel-kasper-cyber/___________About the host Anthony Hess:Anthony is passionate about cyber insurance. He is the CEO of Asceris, which supports clients to respond to cyber incidents quickly and effectively. Originally from the US, Anthony now lives in Europe with his wife and two children.Get in touch with Anthony on LinkedIn: https://www.linkedin.com/in/anthonyhess/ or email: [email protected].___________Thanks to our friends at SAWOO for producing this episode with us!