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.

If you enjoyed this episode, be sure to subscribe to Beyond the Desk, leave a review and share it with someone in your network.

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

In this episode of Beyond the Desk: Underwriting Edition, Sanjeev Vegad sits down with Mark Fellows, Divisional Director, Financial Lines, International at Westfield Specialty, to explore a career that spans claims, underwriting, leadership, and multiple successful business builds across the London insurance market.

Mark shares how he accidentally fell into insurance after university, why a move to Swiss Re completely changed the trajectory of his career, and what he has learned from building underwriting platforms from scratch. He also offers a candid view on the current financial lines market, the rise of broker facilities, and the opportunities and risks that AI presents for the next generation of underwriters.

This episode is packed with practical leadership advice, insights into market cycles, and a reminder that deep expertise, curiosity, and strong relationships remain the foundations of great underwriting.

• How Mark went from claims into underwriting almost by accident
• Why he believes leadership is about responsibility, not hierarchy
• What he looks for when hiring underwriters and building high-performing teams
• The realities of launching and growing an underwriting business from zero
• How Westfield Specialty has positioned itself in a highly competitive market
• His perspective on the current soft market and the impact of broker facilities
• Why AI will transform insurance—but shouldn't replace human judgement
• The biggest mistake young underwriters can make in their early careers
• Why reading, asking questions, and being in the office still matter
• The career advice he wishes he had taken himself

• Build deep expertise before chasing seniority.
• Great underwriting teams are built around culture, trust, and collaboration.
• Differentiation comes from people, service, and execution.
• AI should enhance underwriting, not replace relationships and judgement.
• The best opportunities often come from being willing to build something new.

Whether you're an underwriting assistant, an experienced underwriter, or a leader looking to build the next successful platform, this conversation offers a thoughtful and practical look at what long-term success in insurance really looks like.

In this episode of Beyond the Desk, host Sanjeev Vegad is joined by Talbir Singh Bains, founder of Volante Global and one of the insurance industry's most respected entrepreneurs.

Talbir reflects on a career spanning QBE, Willis Re, Swiss Re, Dual and the creation of Volante, sharing the lessons that shaped his leadership philosophy and entrepreneurial mindset.

The conversation explores how to build a business that aligns with capital, why culture should be lived rather than written down, the future of MGAs, attracting the next generation of insurance talent, and why the industry's greatest purpose is helping society recover from risk.

Whether you're an aspiring leader, underwriter, entrepreneur or simply interested in building great businesses, this episode is packed with practical insights and thought-provoking advice.

• How Talbir's career evolved from actuarial pricing into entrepreneurship.
• The lessons he learned from leaders at QBE, Willis Re, Swiss Re and Dual.
• Why Volante was built on a fundamentally different business model.
• How to balance growth with long-term underwriting profitability.
• Why culture is created through actions—not policies.
• What makes MGAs so attractive to underwriting talent.
• Why diversity and young talent are essential for innovation.
• The qualities future insurance leaders should develop.
• Why insurance plays a far greater role in society than many people realise.

Sustainable growth always beats growth for growth's sake.

The strongest businesses succeed when their interests are fully aligned with their investors and capital partners.

Great cultures are built through consistent leadership behaviours, not company policies.

Innovation comes from fresh thinking, diverse perspectives and empowering the next generation of leaders.

Insurance is ultimately about helping people and businesses recover when the unexpected happens.

If you enjoyed this episode, be sure to subscribe to Beyond the Desk, leave a review and share it with someone in your network.

Connect with Sanjeev Vegad and Talbir Singh Bains on LinkedIn to continue the conversation.

In this special Beyond the Desk: Underwriting Edition, host Sanjeev Vegad sits down with Simon Jackson, CEO of Amwins Underwriting, to discuss what it takes to build high-performing underwriting teams, embrace calculated career risks, and lead through one of the insurance industry's most transformative periods.

Drawing on leadership experience at Amlin, Beazley and now Amwins, Simon shares the lessons that have shaped his career, from developing underwriting talent and expanding international teams to navigating the rise of MGAs, artificial intelligence and changing market dynamics.

The conversation explores why underwriting remains a people business, how technology should empower rather than replace underwriters, and why curiosity may be the most valuable skill for the next generation entering the profession.

Whether you're an aspiring underwriter, experienced market professional or insurance leader, this episode is packed with practical insights on leadership, growth and the future of the industry.

How Simon's career evolved from traditional underwriting into executive leadership.

Why the best career moves often involve stepping outside your comfort zone.

The difference between being a great underwriter and a great underwriting leader.

How AI and technology are changing underwriting without replacing human judgement.

Why curiosity and relationship-building remain essential skills.

The opportunities and challenges facing MGAs.

How to build strong underwriting cultures across multiple locations.

Simon's outlook for the future of the Lloyd's and specialty insurance markets.

The best leadership opportunities often feel uncomfortable at first.

Great underwriters don't automatically become great leaders—leadership requires adaptability and emotional intelligence.

Technology should empower underwriters, not replace their judgement.

Curiosity, client engagement and relationship-building will always be competitive advantages.

Building successful teams starts with culture, trust and empowering people to make decisions.

Taking informed career risks often leads to the greatest long-term rewards.

Stay curious throughout your career.

Take calculated risks rather than waiting until you're completely comfortable.

Build genuine relationships across the insurance market.

Learn the businesses and industries you're underwriting.

Adapt your leadership style to your audience.

Use technology to make better decisions, not to replace them.

What does it actually take to go from growing up in one of Glasgow's most deprived areas to becoming a CEO in the insurance industry without a university degree, without a clear plan, and without ever making CEO your goal?

In this episode of Beyond the Desk, Mark Thomas sits down with Chris Barclay, CEO of Superscript, for one of the most candid career conversations the show has delivered. Chris traces 20+ years across claims, loss adjusting, commercial leadership, and insurtech including stints at Norwich Union, Crawford & Company, Thistle, and Marsh before joining Superscript as Chief Commercial Officer and being appointed CEO just over a year ago.

Chris opens up about the Glassdoor review that triggered genuine anxiety, the imposter syndrome that hit when he became CEO, the six months he spent trying to be someone else, and what pulled him back to himself. He also shares his take on AI in digital broking Superscript's mantra of "enabled by tech, powered by people" along with his three-year growth roadmap and a frank view on the talent and work ethic challenges facing insurance today.

Key topics include: non-traditional career paths in insurance, claims as a leadership foundation, turnaround leadership, CEO transition, mental health and resilience, insurtech strategy, and AI in broking.

If you work in insurance technology, broking, or insurtech or you're an ambitious leader trying to figure out what the next step looks like then this one is for you.

In this episode of Beyond the Desk, Mark Thomas is joined by Sally Peace, Chief of Staff and HR Director at Apollo, to discuss an unconventional career that has spanned actuarial science, catastrophe modelling, operations, business planning, HR and executive leadership.

Sally shares how embracing opportunities, rather than following a rigid career plan, helped shape her journey into one of the most unique leadership roles in the insurance market.

The conversation explores leadership, company culture, mentoring, diversity, flexible working, AI's impact on talent, and why saying "yes" before you feel completely ready can be one of the most powerful career decisions you'll ever make.

Whether you're leading teams today or aspiring to leadership tomorrow, this episode is packed with practical advice and honest reflections.

• Why you don't need a five or ten-year career plan.
• How sideways career moves often create the best leaders.
• The difference between management and leadership.
• Why confidence grows after saying yes not before.
• How Apollo approaches culture and flexible working.
• The role HR should really play in shaping a business.
• Why communication is leadership's most important skill.
• How AI is changing talent development in insurance.
• Why mentoring and coaching can accelerate your growth.

Careers don't have to follow a straight line embrace opportunities that stretch you.

Great leaders listen more than they speak.

Culture isn't created by HR alone it's everyone's responsibility.

Flexible working works best when it's built on trust rather than rigid policies.

Confidence comes from doing difficult things, not waiting until you feel ready.

AI won't replace great people but it will change the skills organisations need.

If you enjoyed this episode, make sure you subscribe to Beyond the Desk, leave a review and share it with someone in your network.

You can connect with Mark Thomas and Sally Peace on LinkedIn to continue the conversation.