What does it take to build a successful career in underwriting?

In this episode of Beyond the Desk Underwriting Edition, Sanj Vagad is joined by Charles Boorman to explore a career spanning broking, D&O, financial lines, underwriting leadership, turnarounds and the MGA market.

Charles shares how he first fell into insurance before discovering that specialising in D&O was the turning point that made him realise he could genuinely add value to clients. He talks through his move from broking into underwriting at QBE, taking on the leadership of an FI team outside his comfort zone, and the experiences that shaped his approach to building and turning around underwriting businesses.

The conversation also explores Charles' move into the MGA world and why an incubator-style model gave him the opportunity to focus on underwriting, building a team and growing a business without taking on the same level of risk as a traditional MGA start-up.

Sanj and Charles discuss the challenges of turning around an underwriting business, including managing people, maintaining broker relationships and communicating difficult decisions. Charles also shares his perspective on the current D&O and FI markets, the impact of increasing capacity and competition, and whether combining commercial D&O and FI underwriting makes sense.

Towards the end of the episode, Charles offers advice to underwriters looking to broaden their experience, emphasising the importance of taking baby steps, learning from experienced people and getting outside your comfort zone.

• How Charles accidentally fell into insurance
• Why specialising in D&O changed the trajectory of his career
• Making the move from broking into underwriting
• Taking on an FI leadership role outside his comfort zone
• The challenges of building and turning around underwriting businesses
• Why people are often the hardest part of a turnaround
• The importance of communication and broker relationships
• Charles' transition into the MGA market
• The advantages of an incubator-style MGA model
• Current dynamics across the D&O and FI markets
• Whether commercial D&O and FI should be brought closer together
• How underwriters can broaden their class experience
• Why taking "baby steps" matters when learning a new product
• The importance of concentrating on your strengths and managing your weaknesses
• Why getting outside your comfort zone is where you learn and grow

Charles also reflects on the career decisions that changed his own trajectory and why his biggest advice is simple: when an opportunity comes to step outside your comfort zone, put your hand up and say yes.

What can we learn from the people shaping the future of insurance?

In this special highlights episode of Beyond the Desk, Mark Thomas brings together some of the most insightful moments from conversations with senior leaders across the global insurance industry.

Across the series, guests have explored everything from leadership and career development to AI, underwriting, talent, culture and the changing insurance market.

This episode brings those conversations together, highlighting some of the biggest ideas, lessons and predictions from the people working at the forefront of the industry.

• Nigel Walsh: on the leap of faith it took to move his family to New York for an opportunity at Google and how AI is reshaping underwriting and claims.
• Christopher Barclay: Imposter syndrome stepping into a CEO role and the moment he realised that being himself was the key to leading successfully.
• Kirk Southern: on leadership, career development, the evolving role of the Chief People Officer and how businesses can use AI to empower their people.
• Carys Lawton-Bryce: sharing perspectives on people, culture and the changing world of work.
• John Wingate: exploring technology, AI and the opportunities emerging from rapid technological change.
• Sally Peace: discussing culture, leadership and building successful businesses as organisations grow.
• Simon Jackson: from the Underwriting mini-series, exploring the future of underwriting and the changing role of technology.
• Talbir Singh Banes: on underwriting leadership, talent and the evolution of the MGA market.
• Mark Fellows: sharing lessons from a career in underwriting, building teams and developing underwriting businesses.
• Scott Bailey: discussing underwriting, AI and why human expertise and relationships will continue to matter.

Leadership & career development

Why curiosity, humility and a willingness to learn can be more valuable than trying to accelerate your career too quickly. Kirk, for example, reflects on the importance of learning the foundations of a role and the people who helped shape his career.

The future of AI

How AI could transform the way insurance businesses operate, while still leaving human judgement, relationships and expertise at the heart of the industry.

Underwriting

What makes a great underwriter, what makes a great underwriting leader, and how technology can augment rather than replace underwriting expertise.

Talent & culture

How insurance businesses can attract, develop and retain the people they need as the skills required across the industry continue to change.

The changing insurance market

From the growth of MGAs and delegated authority to changing market cycles and the evolving role of technology, the series explores where the industry could be heading next.

Human expertise in an increasingly automated world

One recurring message throughout the conversations is that technology can remove repetitive work and enhance decision-making, but insurance remains fundamentally a relationship-driven business.

As technology transforms the way insurance works, what will remain uniquely human?

From leadership and culture to underwriting expertise and broker relationships, this episode brings together the ideas that could shape the next chapter of the insurance industry.

In this episode of Beyond the Desk, Underwriting Mini Series, host Sanj Vagad sits down with Scott Bailey, Head of Global Cyber Underwriting at CFC.

Scott looks back on a career spanning 25 years in cyber insurance, from joining Click for Cover (later CFC) as employee number two in 2001, through spells at CNA Hardy and Markel, to his return to CFC three and a half years ago. Along the way, he shares how the cyber market was built from scratch, why the SME protection gap remains so wide, where we are in the current pricing cycle, and why AI is both the biggest emerging threat and one of the industry's best defensive tools.

Whether you're an underwriter, broker or simply curious about how one of insurance's youngest classes of business came to be, this episode is packed with first-hand insight from one of the market's most experienced cyber leaders.

In This Episode You'll Learn

How Scott's career began in car insurance telesales before he joined Click for Cover (later CFC) as employee number two in 2001

What it was like building the cyber insurance product from scratch – before regulation, actuarial data, or even market awareness of the risk existed

The lessons learned moving between an MGA (CFC) and carrier platforms (CNA Hardy, Markel)

Why Scott returned to CFC after a decade away, and the difference between heading global cyber and heading global cyber underwriting

Why only 10–15% of SMEs in developed economies buy cyber insurance, and what the industry needs to do about it

Where we are in the cyber insurance pricing cycle, and why the market may need to firm up in certain geographies

Why AI is both the biggest emerging cyber threat and one of the sector's best defensive tools

Scott's advice for underwriters early in their career, and why curiosity is the most valuable skill in the market

Key Takeaways

Cyber insurance was built from scratch, with 25 years of data now one of CFC's biggest advantages – even though the fast-changing nature of the class limits how much any historical data set can really tell you.

MGAs and carriers each carry different risks and rewards; being nimble matters most in a fast-evolving class like cyber.

The SME cyber protection gap comes down to education, not price – the best policies offer far more value than indemnity alone.

Cyber pricing has softened for three years following the 2021/22 correction, but a well-diversified portfolio matters given the ongoing ransomware and AI threat.

AI is a double-edged sword for cyber insurance, a growing attack vector, but also a powerful underwriting and defensive tool.

Curiosity and a willingness to ask questions is, in Scott's words, one of the most valuable traits an underwriter can have.

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Connect with Sanj Vagad and Scott Bailey on LinkedIn to continue the conversation.