Just a quick note that we are taking a short break for a couple of weeks to enjoy the summer, but the rest of Season 7 will be back soon!

In the meantime, this is a great opportunity to catch up on the back catalogue of the show, or get The Future of Insurance books from Audible to keep listening to inspiring stories of how companies in the insurance industry are overcoming challenges, innovating and evolving.

Just visit www.future-of-insurance.com or search for The Future of Insurance on Audible or Amazon.

Episode Info

Mary Boyd is a seasoned senior executive with over 30 years of experience leading businesses through transformative phases in their history that span invention, renovation, integration and rebuilding. Beyond her reputation for building, revitalizing, and integrating businesses, Mary has a proven track record of successfully translating strategic vision into reality. Her career is distinguished by spearheading large-scale operational, technological, and team transformations, driving significant growth and innovation across organizations. Mary’s success lies in her ability to blend innovation with an agile approach, excelling at both seeing the big picture and identifying strategic opportunities in the finer details.

Since 2006, Mary has held CEO, President and division leadership roles, consistently improving net income by optimizing channel economics, fostering best-in-class partnerships, building high-performance teams, and advancing operational excellence. 

Mary currently serves as Chief Executive Officer of Hiscox USA, leading the business through its next phase of growth and commitment to supporting the small business landscape. In her role, Mary oversees the financial operations of Hiscox USA’s nearly $1 billion commercial property and casualty business. She collaborates closely with her teams to drive near-term profitable growth while implementing a strategic vision that will markedly expand their reach to more of America’s entrepreneurs.

Mary joined Hiscox from Plymouth Rock Assurance Corporation, where she served as President and CEO of their Independent Agency Group, overseeing personal insurance and commercial auto businesses. Before that, she led Hartford’s personal lines Direct-to-Consumer and Agency channels, following 15 years in high-net-worth personal lines. Mary began her insurance career at Chubb as an actuarial trainee, progressing through roles in Product and Pricing. She ultimately launched the Predictive Analytics practice for Chubb’s Personal Lines division and later spent five years at ACE (now Chubb), where she served as President of their Private Risk Services division. 

Mary earned her Bachelor of Arts degree in Applied Mathematics and Economics from Rutgers University. As a coach of youth sports, ambitious professionals, and entrepreneurs 

Episode Highlights

Introduction and Background

• Mary shares her experience and background in the insurance industry, highlighting her 30-year career and her role at Hiscox USA.

• Hiscox USA, part of a long-standing London-based company, started its operations in the US in 2006.

Business Model and Growth

• Hiscox USA has transformed the small commercial business sector by offering online binding and digital partnerships, expanding its business to nearly a billion dollars.

• The company operates as an omnichannel business, engaging in direct sales, digital partnerships, and wholesale brokerage.

Challenges and Opportunities

• The conversation touches on the challenges small business owners face, such as being underinsured, and how Hiscox aims to support them through education and tailored insurance solutions.

• The company is focused on being a leading insurer for entrepreneurs, emphasizing the need for holistic support beyond just sales.

Innovation

• The discussion emphasizes the importance of AI and advanced tools in improving underwriting and efficiency across the insurance value chain.

• Hiscox has partnered with Google to leverage AI for better underwriting and insights.

Future Outlook

• Mary discusses the future of Hiscox, highlighting the integration of data and analytics to enhance product offerings and maintain competitivenes.

• The company aims to continue its growth by being a better partner and protector for businesses, focusing on insights and protection rather than just speed.

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

As innovation continues to change at a relentless pace, cutting through a noisy marketplace has never been more essential.

Such change brings exciting opportunities but also potential risks. Solve the right issues with the right tech, and you can bolster bottom lines and future-proof operations. Identify the wrong challenges and the wrong technology, and you risk trust, reputation, and even market share.

Learn how to identify the right opportunities with MetLife's Bill Pappas in this episode from our conversation on the main stage at ITI NYC 2025 session, 'From Enable to Empower:

Harnessing Technology to Drive Business Growth.' Join us as Bill outlines the innovations that help shape MetLife's strategy and how his team has evolved tech deployment from an enabler to an empowerer of business growth.

Episode Summary

The episode discusses the evolving role of technology and AI in business operations, particularly at MetLife. Bill Pappas, a leader in technology and operations, highlights the integration of traditional technology with client experience and operational processes. He emphasizes the importance of adapting to rapid technological changes and the need for new execution playbooks, as traditional methods become obsolete quickly.

The discussion also covers the balance between human and AI collaboration, suggesting that while AI presents significant opportunities, humans will continue to play a crucial role, especially in areas requiring critical thinking. Bill stresses the importance of a commercial mindset for business leaders, understanding both the financial aspects and the competitive landscape.

Furthermore, the Bill addresses the challenges of digital transformation, noting that many companies struggle with integrating new tools into existing ecosystems due to legacy technical debt and fragmented data. He advises business leaders to focus on the value proposition of new technologies and ensure their data is fit for purpose.

1. Role of Technology and AI:

   • Exploration of how technology and AI are transforming business operations at MetLife.

   • Integration of traditional technology with client experience and operational processes.

2. Adapting to Technological Changes:

   • Importance of adapting to rapid technological advancements.

   • Need for new execution playbooks as traditional methods become quickly outdated.

3. Human and AI Collaboration:

   • Discussion on the balance between human roles and AI capabilities.

   • Emphasis on the continued importance of human involvement in areas requiring critical thinking.

4. Commercial Mindset:

   • Importance of a commercial mindset for business leaders.

   • Understanding financial aspects and the competitive landscape.

5. Challenges of Digital Transformation:

   • Challenges companies face with digital transformation.

   • Issues with integrating new tools due to legacy technical debt and fragmented data.

6. Focus on Value Proposition:

   • Advice for business leaders to focus on the value proposition of new technologies.

   • Ensuring data is fit for purpose to maximize technology benefits.

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 Merideth is a seasoned insurance industry professional, public policy strategist, and Republican candidate for Oklahoma Insurance Commissioner in 2026. With a career spanning agency operations, catastrophe response, and legislative advocacy, Chris brings a rare 360-degree view of the insurance ecosystem—having worked with agents, adjusters, consumers, and lawmakers from across the country.

Currently serving in government affairs for a major national carrier, Chris has been on the front lines of some of the most pressing issues facing the market: skyrocketing premiums, litigation abuse, disappearing availability, and the urgent need for property resilience in a high-risk state like Oklahoma.

Chris’s campaign is built on grassroots leadership, free-market reform, and a clear promise: make insurance work for people again. His bold policy agenda includes reducing reinsurance pressure, incentivizing fortified home construction, streamlining regulatory red tape, and launching transparency tools like a Prior Authorization Report Card and a Claims Complaint Scoreboard.

Known for his energy, grit, and straight talk, Chris is leading a grassroots movement of agents and consumers to restore trust and accountability in the insurance system—before it’s too late.

Follow his campaign at www.ChrisMeridethForOK.com

Episode Summary

The video features a conversation with Chris Meredith, a candidate running for the position of Commissioner of Insurance in Oklahoma. The discussion centers around the challenges and solutions related to insurance and fortified homes in the state. Here are the key points covered in the video:

1. Background and Motivation:

   • Chris emphasizes that their campaign is not about politics but about protecting people and doing the right thing.

   • He has extensive experience in the insurance industry, having worked across various states and attended national meetings.

2. Insurance Challenges:

   • There is a nationwide issue with insurance affordability, where people struggle to afford insurance, and carriers find it economically challenging to provide coverage.

   • The frequency and severity of storms, particularly hailstorms, are increasing, making it more likely for homes to be hit.

3. Fortified Homes Initiative:

   • Chris advocates for fortified homes, which are designed to withstand severe weather conditions. This includes using hail-resistant shingles and securing roof decking.

   • They highlight the success of similar programs in Alabama and stress the need for Oklahoma to adopt these best practices.

4. Legislative and Grassroots Efforts:

   • Chris discusses the importance of legislative changes and grassroots efforts to push for fortified home initiatives.

   • He emphasizes collaboration over conflict, urging local agents, roofers, and contractors to work together to influence legislative priorities.

5. Future Plans and Commitment:

   • Chris is committed to implementing these initiatives if elected, drawing on private funding and legislative support.

   • He expresses a personal connection to the cause, having witnessed the impact of insurance in disaster recovery.

OverallOverall, the interviedw highlights Chris's vision for improving insurance practices in Oklahoma through fortified homes and collaborative efforts.

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

Over the last decade, the insurtech landscape has rapidly evolved, transitioning from a space dominated by startups innovating at the fringes to becoming a thriving industry amassing huge investment and innovation.

But how did we get here, and more importantly, where do they go next?

Hippo CEO, Rick McCathron, joins Bryan Falchuk for this conversion, titled, "A Decade of Insurtech: From Startup to Success Story in 10 Years," recorded live from the main stage of ITI NYC 2025. Rick reflects on a decade of progress at Hippo, exploriing the strategies that have propelled insurtechs from industry disruptors to established market players, offering insights into what it takes to scale, sustain growth, and maintain operational excellence.

Episode Summary

This episode provides insights into effective sales and networking strategies for those selling to insurance companies. It challenges conventional sales tactics and emphasizes the importance of personalized and informed approaches.

Industry Challenges and Adaptation

Rick emphasizes the dynamic nature of the business world, noting that successful companies are those that can pivot and adapt quickly to new learnings, data, and shifts in consumer appetites.

He shares insights on the importance of making decisions with imperfect information and the need to adjust those decisions as more information becomes available.

Financial Performance and Future Outlook

Hippo has successfully met and exceeded its financial metrics, and Rick expresses confidence in the company's ability to continue this trend. He mentions an upcoming presentation to the investment community to outline their future plans.

Customer Experience and Industry Transformation

The discussion touches on the need for the insurance industry to improve customer experience, drawing parallels to Amazon's customer-centric approach. Despite progress, Rick believes there is still room for improvement.

Transparency and Management

Rick highlights the importance of transparency and ownership in management, acknowledging past mistakes and the need for change. He credits Hippo's management team for their ability to adapt and overcome challenges.

Collaboration and Industry Opportunities

The conversation also covers the need for collaboration within the industry, emphasizing that there is ample opportunity for different companies to succeed without a winner-takes-all mentality.

OverallThe interview provides a comprehensive look at Hippo Insurance's strategies, challenges, and future plans, along with broader insights into the insurance industry's evolution.

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

After a series of conferences where I saw some sales tactics that were having the opposite effect from what the person employing them would have wanted, I thought I'd use an episode to share some of the advice I give to companies I've advised over the years. It's informed by my direct experience having been an executive at insurance companies who got sold to, and running the sales function for a B2B SaaS insurtech solution provider.

Hopefully this is valuable to anyone trying to sell into the insurance industry (and to those of us on the receiving end of those sales efforts!).

Episode Summary

This episode provides insights into effective sales and networking strategies for those selling to insurance companies. It challenges conventional sales tactics and emphasizes the importance of personalized and informed approaches.

Key Points:

1. Personalized Outreach:

   • Avoid blanket approaches like mass emails or messages. Instead, invest time in understanding if the recipient is a genuine prospect.

   • Tailor your messages to address specific needs and demonstrate genuine interest.

2. Challenges with Conventional Tactics:

   • Many sales playbooks advocate for reaching out to everyone, but this often leads to brand damage and wasted efforts.

   • The video argues that the insurance industry requires a different approach due to its unique nature.

3. Effective Networking:

   • Utilize platforms like LinkedIn for meaningful connections rather than relying solely on event apps, which are often underutilized.

   • Be mindful of social etiquette, such as not interrupting ongoing conversations or meetings.

4. Building Relationships:

   • Focus on being informed and culturally aware to foster genuine relationships.

   • The goal is to reach a point where the prospect feels understood and sees you as a potential solution to their challenges.

5. Practical Advice:

   • Spend a few moments researching potential clients to ensure they are the right fit.

   • Be upfront about your intentions to avoid wasting time on both sides.

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

Luca Russignan is an insurance expert with more than 15 years of experience with industry-leading consultancies and insurers. At Capgemini, he enables CxO conversations in the insurance sector through data-driven thought leadership to shape insurance business strategy focusing in particular on North America and Europe. He holds an MBA in Strategy and Finance from Hult International Business School.  

Episode Summary

The interview discusses the future of the insurance industry, focusing on demographic changes and the role of technology, particularly AI, in shaping this future. Overall, the interview provides a forward-looking analysis of the insurance industry, urging stakeholders to consider demographic trends and technological advancements in their strategic planning.

Key Points:

1. Demographic Shifts:
   • The interview highlights a significant demographic shift where the population pyramid is flipping, meaning there will be more older people than younger ones. This change is expected to fundamentally alter who buys insurance, the risks they face, and how these risks interconnect.
2. Actionable Insights:
   • The discussion emphasizes the importance of making insights actionable. The goal is not just to provide new information but to explain why it matters and how to start acting on it. This involves connecting future forecasts with present-day actions.
3. Role of AI:
   • AI is seen as a silver lining, offering opportunities to address challenges like a shrinking workforce and climate change. It is viewed as a tool that can enable successful aging of the population and unlock productivity gains.
4. Strategic Conversations:
   • The interview stresses the need for integrating demographic considerations into strategic conversations today. This integration is crucial for preparing for future challenges and opportunities.
5. Future Projections:
   • The interview looks ahead to 2050, considering how current trends will evolve. It encourages taking "no regret" actions today that will be beneficial regardless of how the future unfolds.

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

Debbie Brackeen leads CSAA Insurance Group in strategy, partnerships, innovation and venture investing. She has more than 25 years of experience and leadership at innovative high-tech companies, including Apple, Sun, HP, and eBay, and, most recently, serving as the global head of innovation at Citigroup. She has served as an adviser to the Astia Technology Committee since 2008, and was an adviser on the corporate board of the National Venture Capital Association. Ms. Brackeen earned a degree in American Studies from Stanford University and has completed executive programs at the Northwestern Kellogg School of Management, INSEAD and the Stanford Graduate School of Business.  

Highlights from the Show

The video features a discussion with David, who has over 35 years of experience in the insurance industry, focusing on casualty underwriting and management. He currently serves as the Head of Casualty at Argo Group, where he oversees various liability lines, including primary and excess casualty, environmental liabilities, construction liabilities, and workers' compensation. The conversation highlights Argo's niche focus on the U.S. market, with some operations in Bermuda, and its recent acquisition by Brookfield Wealth Solutions.

David shares insights into the challenges faced by the Casualty insurance sector, such as social inflation, litigiousness in the U.S., and the economic viability of Casualty lines. He discusses the importance of capacity management and the need for insurance carriers to be nimble in managing their portfolios. The conversation also touches on the impact of distracted driving on auto insurance claims and the necessity for the industry to adapt to changing conditions.

The video concludes with a discussion on the future of the insurance industry, emphasizing the need for innovation and the importance of attracting new talent to sustain the industry. David expresses optimism about the industry's ability to adapt and continue providing necessary coverage despite current challenges.

Episode Summary

The video features a discussion on the strategic implementation of Artificial Intelligence (AI) within a corporate setting, specifically focusing on the insurance industry. The conversation is led by Debbie Brackeen, who heads innovation and corporate development at CSAA Insurance Group, a part of the AAA insurance companies in the US. 

Key Points

1. AI Strategy and Implementation: The focus is on harnessing the power of Generative AI (Gen AI) to transform business operations and create sustainable business value. The strategy involves embedding AI as a strategic capability within the company to gain a competitive advantage.

2. AI in Insurance: The conversation highlights the potential of AI to revolutionize the insurance industry by improving efficiency and accuracy in claims processing and underwriting. The use of AI is seen as a way to manage both structured and unstructured data more effectively.

3. Challenges and Opportunities: There is an acknowledgment of the challenges posed by AI, such as the need for governance, controls, and regulatory compliance. However, the potential benefits, such as faster claims processing and better customer service, are emphasized.

4. Future Outlook: The discussion reflects optimism about the future impact of AI, comparing its transformative potential to that of the Internet. There is a belief that AI will lead to new job roles and opportunities, rather than just eliminating existing ones.

Overall, the video provides insights into how AI is being strategically integrated into business processes to enhance efficiency and create new opportunities within the insurance sector.

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

David Corry joined Argo Group in September 2020. As Head of Casualty, he is responsible for leading Primary Casualty, Excess Casualty, Construction, Environmental, Rockwood, and Bermuda Casualty.  Corry previously served as Senior Vice President, Head of Environmental at Argo Group. He has in-depth experience in all lines of casualty insurance, having served as Senior Director at Markel Specialty and Vice President at Liberty Mutual. He also held senior positions at Chubb and Crum & Forster. Corry is a veteran of the armed forces, having served for 29 years in the Air National Guard, retiring with the rank of Lieutenant Colonel. 

Highlights from the Show

The video features a discussion with David, who has over 35 years of experience in the insurance industry, focusing on casualty underwriting and management. He currently serves as the Head of Casualty at Argo Group, where he oversees various liability lines, including primary and excess casualty, environmental liabilities, construction liabilities, and workers' compensation. The conversation highlights Argo's niche focus on the U.S. market, with some operations in Bermuda, and its recent acquisition by Brookfield Wealth Solutions.

David shares insights into the challenges faced by the Casualty insurance sector, such as social inflation, litigiousness in the U.S., and the economic viability of Casualty lines. He discusses the importance of capacity management and the need for insurance carriers to be nimble in managing their portfolios. The conversation also touches on the impact of distracted driving on auto insurance claims and the necessity for the industry to adapt to changing conditions.

The video concludes with a discussion on the future of the insurance industry, emphasizing the need for innovation and the importance of attracting new talent to sustain the industry. David expresses optimism about the industry's ability to adapt and continue providing necessary coverage despite current challenges.

Key Points:

1. Challenges in Casualty Insurance:

   • Social inflation and increased litigiousness in the U.S.

   • Economic viability of casualty lines.

   • Importance of capacity management and nimbleness in portfolio management.

2. Impact of Distracted Driving:

   • Significant effect on auto insurance claims.

   • Necessity for the industry to adapt to changing conditions.

3. Future of the Insurance Industry:

   • Need for innovation and attracting new talent.

   • Optimism about the industry's ability to adapt and provide necessary coverage despite challenges.

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

The Insurance Industry is facing a number of challenges today. And yet the number of strategies tools we can use to overcome those challenges is equally numerous.

That's the spirit of the conversations my good friend Nick Lamparelli and I get into whenever we talk, and now, you get to hear what we talk about because we got together to take over Dave Wechsler's InsurTech Rap a couple of weeks ago, and I am releasing that episode on my show for all of you!

Highlights from the Show

The interview delves into the current challenges and innovations within the insurance market, focusing on the years 2023 and 2024. Key issues discussed include the impact of inflation, tariffs, and natural catastrophes on the industry. The conversation highlights the structural changes in the market, particularly the broken cycle of rate adjustments post-crises, and the ongoing struggle to balance profitability with affordability for both carriers and consumers.

Regulatory challenges, such as difficulties in obtaining rate approvals, are examined, alongside the industry's frustration with continuous rate increases. The discussion also explores innovative solutions like parametric insurance, which offers a viable alternative to traditional models, and emphasizes the importance of diversification in business models, especially for mutual insurers.

The interview touches on the economic effects of tariffs on trade flow and currency attractiveness, as well as the long-term cost of capital. Audience interaction enriches the conversation, providing additional insights into market challenges and potential solutions. The session concludes with gratitude towards participants and a teaser for future discussions on community-based insurance solutions.

Key Points:

1. Market Dynamics and Challenges:
   • The conversation explores the structural changes in the insurance market, emphasizing the broken cycle of rate adjustments following crises.
   • Challenges in finding a balance between profitability and affordability for carriers and consumers are highlighted.
2. Regulatory and Rate Issues:
   • The difficulty in obtaining rate approvals and the impact of regulatory actions on market dynamics are discussed.
   • The conversation touches on the frustration within the industry regarding continuous rate increases and the need for alternative solutions.
3. Parametric Insurance Solutions:
   • The rise of parametric insurance as a viable alternative to traditional models is explored, noting its benefits and cost implications.
4. Diversification and Innovation:
   • The importance of diversification in business models, especially for long-standing mutual insurers, is emphasized.
   • The potential for creative solutions like reciprocal models and community-based insurance solutions is discussed.
5. Impact of Tariffs and Economic Factors:
   • The conversation delves into the effects of tariffs on trade flow, currency attractiveness, and the long-term cost of capital.

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.