The Future of Underwriting: People, AI and Judgment with Simon Jackson

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.

In this episode you'll learn:

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.

Key Takeaways

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.

Key Advice from Simon

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.