The Future of Insurance

Episode Detail
Season 9 of The Future of Insurance opens with a conversation about what happens when a $10 billion specialty insurer decides its own scale isn't a reason to move slowly. Bryan Falchuk talks with Simon Wilson, CEO of Markel Insurance, about his vision for the specialty market through 2030, and the deliberate choice to ask his teams to double their businesses in five years rather than chase another few points of incremental growth. The conversation moves into how that same mindset shows up in Markel's approach to AI: not bolting tools onto individual tasks, but rebuilding entire underwriting processes end to end — from a brand-new AI-native business built and launched in twelve weeks, to a legal document review process that now runs in minutes instead of weeks, to a grassroots fund that hands frontline employees real budget and real autonomy to solve the problems they see every day.
An organization doesn't need to be small or newly founded to reimagine itself. It needs leaders willing to ask a bigger question.
Guest Bio

Simon Wilson is CEO of Markel Insurance, appointed in March 2025 to lead Markel Group's three primary underwriting businesses — Markel Specialty, Markel International, and Markel Global Reinsurance. He was also named an Executive Vice President of Markel Group in February 2026, reporting to Group CEO Tom Gayner. Wilson joined Markel in 2010 to lead international business development and became the primary architect of Markel International's expansion beyond London, scaling operations across Europe, Canada, and Asia to $2.5 billion in annual gross written premium. He was appointed Managing Executive of Global Strategy for Markel in January 2020, then President of Markel International in 2021, a role in which the division grew gross written premiums by nearly 40% and net underwriting profit by more than 250%. Before joining Markel, he led the Lloyd's Asia platform in Singapore, and spent seven years at Lloyd's prior to that. He has more than 20 years of experience scaling large specialty insurance organizations.

Show Notes:

The Doubling Question:
Markel writes roughly $10 billion of the $700 billion global specialty insurance market — Wilson's read: that's room to grow, not a ceiling.

Instead of asking a business leader to grow 5-6%, Wilson asks how they'd double the business in five years, a question designed to surface bigger ideas rather than incremental optimization.

New categories are expanding the specialty pool itself: data center risk, satellite and space exposure, and marine war coverage in the Persian Gulf are all recent, fast-growing additions.

Guardrail on growth: "Top line is vanity, bottom line is sanity." The doubling mindset is paired with underwriting discipline, not a trade against it.

Specialty Insurance's Moment:
Wilson draws a parallel to media: just as audiences moved from four TV channels to infinite, personalized content, commercial insureds increasingly want coverage built around their specific risk rather than a generic product.

He's candid about a unique challenge: people don't want to buy insurance and don't want to use it, which puts pressure on specialty insurers to earn the sale.

Rebuilding AI End to End, Not Task by Task:
Markel Insurance is now organized into 14 business units (roughly 60 specialisms), each with a single accountable leader charged with reimagining their product and process around AI.

Wilson's caution against partial AI adoption: applying it to only one step of a process without rethinking the whole thing creates a bottleneck, "like putting a rocket jet on the back of a bicycle."

Cortex, a new AI-native business built end-to-end on Claude with a pricing engine called Hyperexponential, was built in 12 weeks and targets difficult-to-place US casualty risk.

Markel's Warranties & Indemnities team in London used the legal AI model Harvey to cut the time to reach a decision-ready view on an M&A data room from about a month to roughly seven minutes, with accuracy Wilson estimates at 97%, a five-point improvement in underwriting pick, and premium in that line more than doubling over the past year.

Guardrails, Culture, and Reverse Mentoring:
Every large language model Markel staff use runs inside Markel's own environment so company data doesn't leave the firewall — inside that boundary, teams have wide latitude to experiment.

Markel's Accelerator Fund put $1 million behind ten employee-pitched AI ideas, built out in six weeks; Wilson expects more than $10 million in returns from that investment in its first year.

Wilson credits reverse mentoring — biweekly sessions with a junior colleague — with reshaping how he personally thinks about AI and how the next generation approaches problem-solving.

AI as an Equalizer for Small, Specialized Businesses: Wilson argues AI has democratized technology for niche specialty lines that were previously too small to justify major core-system investment, moving technology decisions closer to the underwriters who understand the customer.

This episode is brought to you by The Future of Insurance book series (future-of-insurance.com) from Bryan Falchuk.
Follow the podcast at future-of-insurance.com/podcast for more details and other episodes.
Music courtesy of Hyperbeat Music, available to stream or download on Spotify, Apple Music, and Amazon Music and more.

Episode Info

Chris is a business-facing CIO and CTO level technology leader with over 10 years in London Market environments and 25+ years across insurance. He is typically brought in to reset technology functions, lead complex regulated transformation, and help businesses use data, automation and AI to improve control, decision making and pace of delivery. His experience spans carriers, syndicates, delegated operations, underwriting, claims and claims services, combining cloud and infrastructure oversight, architecture governance, modern engineering and operating model change.
Chris has held executive roles at Ki Insurance, Crawford & Company, Hiscox, QIC and Capco, where he has built and reshaped technology functions, modernised core systems, led carve outs and integrations, and improved resilience, insight and execution across multi-country operations. He is strongest in high pressure environments that require commercial grip, disciplined delivery and visible executive leadership, helping businesses apply AI with purpose to simplify operations, strengthen performance and move technology teams forward.

Episode Overview:

Data & Customer Experience: The ongoing need for better data is being addressed by AI, enabling more personalized customer experiences that cater to different needs and preferences.
AI's Practical Applications:
AI is being used for advanced data analysis, claim modeling, and improving underwriting accuracy.

It assists in processing information faster, enhancing efficiency in areas like claims.

AI can work with legacy systems, offering capabilities without immediate costly overhauls.

Human-AI Collaboration:
AI is seen as a tool to augment human capabilities, not replace them.

It aims to reduce mundane tasks, allowing humans to focus on complex issues, empathy, and innovation.

The "human in the loop" is still considered vital for oversight and decision-making.

Responsible Adoption: Implementing AI requires a strategic, responsible approach that considers the workforce, fosters a positive culture, and drives genuine operational improvements rather than just surface-level changes.
Democratizing Technology: AI tools have the potential to benefit businesses of all sizes, including niche and specialized insurers, by enabling custom application development and process optimization.
The Road Ahead: While challenges exist, the focus is on embracing AI's potential to create new opportunities, improve productivity, and ensure the industry remains relevant and innovative. The key is a proactive and adaptive mindset.
This episode is brought to you by The Future of Insurance book series (future-of-insurance.com) from Bryan Falchuk.
Follow the podcast at future-of-insurance.com/podcast for more details and other episodes.
Music courtesy of Hyperbeat Music, available to stream or download on Spotify, Apple Music, and Amazon Music and more.

Episode Info

Jason Cass is the co-owner of The Insurance Alliance, co-owner of Virtual Intelligence, founder of Agency Intelligence, and one of the most recognized voices in the independent insurance industry. A veteran agency owner, speaker, and podcaster, he built a profitable three-location agency that runs both virtually and digitally. He was named Illinois Young Agent of the Year in 2005, served as Chairman of the National Young Agents Council from 2011 to 2013, and authored Customer Service is Just Foreplay in 2013. His newest book, Future Ready: The Strategic Case for Structure, Routing, and Scale, co-authored with Mitch Gibson, lays out how independent agencies must evolve in the age of AI and automation. Jason hosts the Agent's Influence and Agency Intelligence podcast series and continues to be a leading advocate for independent agents across the country.

Episode Overview:

This episode of The Future of Insurance features Jason Cass, a prominent voice in the independent insurance agent channel, as he discusses the transformative impact of AI on the industry. Cass, who has been in the insurance industry since 2002 and owns multiple companies, shares his insights on how AI, particularly "agentic AI," is poised to reshape the role of agents and brokers.
Key Takeaways:
AI as a Disruptor and Enabler: Cass emphasizes that while AI won't eliminate agents, it will fundamentally change how they operate. He draws parallels to past technological shifts like the internet, noting that while agents feared obsolescence, the channel adapted and evolved. AI, however, presents a more significant shift.

Efficiency and Cost Reduction: AI's primary impact will be on operational efficiency, significantly reducing the cost of labor within agencies. Cass predicts that within two to three years, agencies adopting AI could see their people costs drop from 55-65% of revenue to 20-30%. This translates to substantial savings, enabling agencies to reinvest or grow.

The Evolving Workforce: The adoption of AI will lead to a shift in agency staffing. While immediate layoffs are unlikely, there will be a transition. Smart agencies will retrain existing staff, focusing on tasks that AI cannot perform. The "swing efficiency score" will be crucial in measuring this transition.

Shift in Licensed vs. Virtual Roles: Cass forecasts a significant change in the makeup of agency staff. Agentic bots, costing around $3,000-$5,000 annually, will replace some licensed roles that currently command salaries of $80,000+. Agencies will likely hire more virtual employees at lower costs to manage these bots, leading to a reduction in the number of highly paid, licensed individuals within an agency.

Regulatory and Licensing Considerations: The question of whether AI can be licensed as an agent is a complex one. Cass believes that currently, AI cannot be licensed, and there are significant regulatory hurdles to overcome. He speculates that this may evolve in the future but emphasizes the current need for licensed human oversight.

Opportunities Created by AI: Beyond cost savings, AI opens up new avenues for growth. Cass highlights the potential for AI to help agents better understand risk quality, align clients with the right markets, and navigate the complexities of policy forms and carrier appetites. The emergence of AI itself is also creating a need for new insurance coverages, similar to the rise of cyber insurance.

The Importance of Adoption and Education: Cass stresses that agents who embrace AI will thrive, while those who resist will be left behind. He advocates for education and training within agencies to help staff become comfortable with AI tools like Claude. The "Artificial Intelligence Utilization Score" (AIU) will become a key metric for success.

The Role of Carriers and Technology Providers: Carriers need to adapt by developing their own AI solutions and partnering with agents to facilitate AI adoption. Technology providers must focus on creating practical, integrated solutions that solve real agency problems, such as routing engines that effectively manage the workflow between humans and AI.

Beyond Fear: Embracing the Future: Cass acknowledges the fear surrounding AI but encourages a proactive approach. He believes that embracing AI will lead to greater job satisfaction, improved client service, and a more robust and attractive insurance industry overall. The key is to focus on the opportunities and develop a culture of adaptation.

This episode is brought to you by The Future of Insurance book series (future-of-insurance.com) from Bryan Falchuk.
Follow the podcast at future-of-insurance.com/podcast for more details and other episodes.
Music courtesy of Hyperbeat Music, available to stream or download on Spotify, Apple Music, and Amazon Music and more.

Episode Info

Celebrating her 26th year in the insurance industry, Meg McKeen, CIC, founded Adjunct Advisors LLC in 2018 with the essential belief that we can do more, and better, to support the professionals who choose a career here. Throughout her own career, working as an underwriter, agent, and leader within the industry, Meg has held a seat at the table during thousands of insurance negotiations. As an independent consultant, Meg now holds space at the crossroads of personal and professional development, for individuals and organizations as they grow their sales and leadership acumen through private coaching, consulting engagements, and the podcast she hosts, Bound & Determined℠. Known for her relatability and storytelling, Meg is a sought after speaker for insurance related conferences and events, as well as a regular columnist for Rough Notes magazine, and Meg's contributions to the insurance industry have been recognized with her inclusion in Insurance Business America's Hot 100 and Elite Women for 2021.
A graduate of Illinois Wesleyan University, Meg is currently a digital nomad in the midst of a thoughtful travel adventure. When she's not supporting insurance professionals, you can find Meg putting the "practice" into yoga practice, searching for the best vegan bakery, or cheering on her favorite independent musicians. Learn more at www.adjunctadvisors.com.

Episode Overview:

Meg's Industry Journey: From 26 years in insurance, including a pivotal moment of burnout and transition, to founding Bound & Determined.

The "Bound & Determined" Podcast: Its genesis, purpose to support women in insurance by discussing life beyond the industry, and its evolution into live events and retreats.

Culture and Connection: The significance of authentic connection and community in professional and personal life, contrasting with corporate environments that can stifle open dialogue.

Personal Evolution and Success: How personal growth and changing definitions of success shape our professional paths and the importance of honoring that evolution.

Navigating Change: Strategies for individuals seeking more intentionality and freedom in their careers, even when bound by traditional structures.

The Human Element in Business: Emphasizing that despite technological advancements like AI, human connection and emotional well-being are paramount for organizational success.

The Nomad Lifestyle: Meg's experience with a mobile lifestyle and how it has unlocked business opportunities and facilitated personal experiences.

Advice for Creating Change: Practical steps for embracing curiosity, setting boundaries, seeking supportive communities, and prioritizing action over perfection when launching new ventures.

This episode is brought to you by The Future of Insurance book series (future-of-insurance.com) from Bryan Falchuk.
Follow the podcast at future-of-insurance.com/podcast for more details and other episodes.
Music courtesy of Hyperbeat Music, available to stream or download on Spotify, Apple Music, and Amazon Music and more.

Episode Info

Scott A. White was appointed Commissioner of the Virginia State Corporation Commission's Bureau of Insurance in 2018. He was elected NAIC President in December 2025.
White joined the Bureau as a research analyst in 1998. From 1999 until 2011, he worked as an attorney advising the Bureau on all major insurance regulatory and compliance matters. In 2011 he became head of the Commission's financial services legal division, expanding his practice areas to include securities and banking.
At the NAIC, White has chaired the Financial Condition (E) Committee, the Long-Term Care Insurance (EX) Task Force, and the Southeast Zone. He is a member of the International Association of Insurance Supervisors (IAIS) Executive Committee, Macroprudential Committee, and Insurance Capital Standard Task Force.
White earned a Bachelor of Arts degree from the University of Virginia and a law degree from the University of Missouri. He and his wife, Jodi, have two grown daughters.

Episode Overview:

Key Issues in Virginia:
Affordability and Availability: While Virginia generally has good market availability, the state is addressing rising premiums and legislative interest in healthcare and property insurance.

Natural Catastrophes: The discussion touches on the impact of weather-related events, with a focus on windstorms, hurricanes, and the often-overlooked risk of flooding.

Risk Mitigation Programs: Virginia is exploring programs to incentivize hardening homes against perils like severe convective storms, including hail and wind.

Litigation and Tort Reform: The conversation addresses the impact of litigation activity on insurance rates and the legislative considerations surrounding tort reform.

The National Conversation on AI:
Industry Adoption: Commissioner White observes that the insurance industry often lags in adopting new technologies like AI, partly due to its inherent risk aversion and the paramount importance of trust.

Consumer Concerns: A significant concern is the potential for AI to be perceived as making critical decisions about healthcare authorization, leading to a growing distrust among consumers.

NAIC's Approach: The NAIC has adopted an iterative approach, starting with principles and moving to guidance through an AI bulletin. Their focus is on compliance, transparency, accountability, and safe systems.

AI Systems Evaluation Tool: The NAIC is piloting a tool to help state insurance departments assess how companies are using AI, focusing on governance and risk management. This aims to identify potential gaps in current laws.

Bias in AI: The discussion highlights the concerns around algorithmic bias and proxy discrimination, while also acknowledging that bias exists in current, non-AI-driven processes. The importance of data protection and operational resiliency against cyber threats is also emphasized.

The Future of Market Regulation:
Modernization Efforts: The NAIC is undertaking an ambitious "Future of Market Regulation" initiative to modernize its approach, recognizing that market regulation has not progressed as rapidly as financial solvency regulation.

Real-Time Surveillance: The goal is to move towards more real-time surveillance of companies, leveraging enhanced data and analysis, rather than relying solely on lengthy, complaint-driven examinations.

Training and Resources: There is a recognized need for regulators to develop new skills and obtain adequate training to effectively oversee AI and other emerging technologies.

This episode is brought to you by The Future of Insurance book series (future-of-insurance.com) from Bryan Falchuk.
Follow the podcast at future-of-insurance.com/podcast for more details and other episodes.
Music courtesy of Hyperbeat Music, available to stream or download on Spotify, Apple Music, and Amazon Music and more.