Inside the Deal

Artificial intelligence is transforming financial services, but how should it be regulated?In this episode of Inside the Deal, we sit down with George Alayon, Assistant Director at the Bermuda Monetary Authority, to discuss the BMA’s recent AI discussion paper and what it means for Bermuda’s insurance and reinsurance market. George shares the regulator’s perspective on balancing innovation with oversight, the opportunities and risks AI presents for financial institutions, and why Bermuda is well-positioned to lead in this space.If you want to understand how AI could reshape compliance, supervision, and the future of insurance, this episode offers insights straight from the source.

In this episode of Inside the Deal, VIPR CEO Paul Templar pulls back the curtain on how his company is transforming the way insurers, MGAs, and TPAs handle data, compliance, and scale. From streamlining bordereaux to unlocking growth opportunities, Paul shares the secrets behind VIPR’s rise and why smarter operations are the key to staying ahead in today’s market.If you’re serious about efficiency, innovation, and the future of underwriting, this is one conversation you don’t want to miss.

In this episode of Inside the Deal, host Helen Souza sits down with InEvo Re's Chief Risk Officer, Andrew Sooboodoo to unpack Oliver Wyman’s recent report examining whether Bermuda’s long-term (re)insurance sector, home to over a $1 trillion in life reserves, poses systemic risk to the global financial system.From stress-test scenarios like credit crises and asset fire sales to the growing influence of private equity ownership, this conversation offers a clear-eyed view of Bermuda’s role as an innovation hub and financial powerhouse. Helen and Andrew explore the island’s regulatory resilience, future challenges, and why global markets continue to look to Bermuda as a trusted jurisdiction.

In this episode of Inside the Deal, we sit down with Mervyn Skeet, CEO of Bermuda's newly formed Corporate Income Tax Agency (CITA), to unpack Bermuda's corporate income tax: what it is, what it’s not, and what it means for the island’s global insurance and reinsurance players. From myths and misunderstandings to strategic implications, this discussion offers clarity on one of the most talked-about developments shaping Bermuda’s position in the global financial services market. Whether you're a CEO, CFO, underwriter, or policymaker, this conversation offers practical insight and real-world perspective.

In this episode of Inside the Deal, we sit down with Martin Wiggins, Founder and CEO of Brandformula, as he shares his unexpected journey from insurance broker to brand strategist. Martin unpacks what inspired his leap into marketing, the value of storytelling in a risk-based industry, and why brand is a strategic asset and not just a logo.We explore the critical differences between a rebrand and a brand refresh, and why getting it right matters more than ever in today’s digital-first world. If you work in re/insurance and want to stay relevant in a competitive, global market, this is an episode you can’t afford to miss.

In this episode of Inside the Deal, we speak with Anirudha Balasubramanian, founder of Tailshift, whose journey from commodities trading to a PhD in market design now fuels a bold reimagining of casualty risk transfer. We dive into Tailshift’s experience in Lloyd’s Lab Cohort 14, their growing footprint in Bermuda across captives, program (re)insurers, and legacy acquirers, and how they’re using AI to bring clarity, speed, and structure to an often opaque market. 

In this episode of Inside the Deal, we sit down with Suzanne Williams-Charles, CEO of Bermuda International Long Term Insurers and Reinsurers (BILTIR), to explore the growing impact and global relevance of Bermuda’s long-term insurance and reinsurance sector. Suzanne shares insights on how BILTIR is advocating for the industry, supporting regulatory engagement, and building awareness of the island’s unique strengths in life, annuity, and retirement risk.Additionally, we discuss key trends shaping the long-term space, the importance of local talent development, and how Bermuda is positioning itself as a forward-looking hub in an evolving global risk environment. Whether you're new to the life and annuity sector or a seasoned player, this conversation offers a sharp look at what’s ahead for Bermuda and BILTIR.

In this episode of Inside the Deal, we sit down with Greg Zarin, founder of Subrosmart, to unpack the often-overlooked world of subrogation and how his firm turned a niche legal service into a global operation. Greg shares the story behind Subrosmart’s humble beginnings and its impressive growth to over 60 team members across three offices, working with more than 40 insurance carriers in the London market.We dive into the mechanics of subrogation, what makes it so critical in today’s claims environment, and how Subrosmart continues to innovate while building lasting partnerships with insurers around the world. It’s a conversation full of practical insights, entrepreneurial grit, and global perspective.

In our final episode of Inside the Deal live from the Bermuda Captive Conference, we wrapped up the week with an insightful and diverse panel of guests who each brought a unique lens to the captive insurance conversation.Carolyn Fahey, Executive Director of AIROC, kicked things off with a discussion on exit strategies for captives, what options are out there, how to plan ahead, and why it's becoming a more prominent topic in today's evolving market.Chiara Nannini of Conyers provided a legal perspective on the changing dynamics in Bermuda’s regulatory landscape and what global clients are looking for when choosing Bermuda as a domicile.Founder of PRP Performa, Hugh Barit, shared a fascinating investor's view into managing captive assets, how the firm has grown in tandem with the Bermuda captive space, and the factors shaping investment decisions today.And finally, Christian Dunleavy, Group President of Aspen Insurance, offered a re/insurer’s take on Bermuda’s strategic position globally, the opportunities for innovation, and Aspen’s ongoing commitment to the market.Each guest shared insights from their area of expertise, their thoughts on Bermuda’s value and of course, their favorite local drink. A perfect close to an insightful week!

Part 1: The final day of Inside the Deal coverage, Kevin Yousif of Yousif Capital Management shared insights on risk financing, capital efficiency, and how captives are adapting to macroeconomic pressures and evolving regulatory demands. He also reflected on Bermuda’s enduring relevance in the global captive market and where strategic focus should lie going forward.Later, we sat down with Tanja Korff of Marsh to explore key takeaways from the past two days, including the shifting needs of captive owners, the emergence of new risk themes, and how managers are helping clients navigate change. Our conversation closed with a forward-looking discussion on talent development and innovation as Marsh helps future-proof the next generation of risk leaders.