INTERVIEW
How AI Is Changing Insurance Work – with Michelle Middleton

Michelle Middleton, Chief Operating Officer at Fall Line Specialty, discusses talent, technology, and AI.
As insurers face a growing talent gap and increased pressure to modernize, Michelle reflects on her career in insurance while discussing talent, technology, and what AI means for the future of the industry. Drawing on decades of experience, she shares insights on how insurers can attract the next generation of talent, adapt to ongoing technological change, and adopt AI in practical, responsible ways.
The Roots team would like to thank Michelle Middleton for participating in this interview.
Why It Matters
As insurers face a growing talent gap and rising pressure to modernize, AI is reshaping how insurance work gets done. This conversation explores how talent, technology, and AI intersect in today’s insurance organizations.
Episode Highlights
- The insurance talent gap is accelerating as long-standing training programs disappear and younger workers expect faster growth and modern tools.
- Technology has consistently increased speed and expectations in insurance without replacing the importance of human judgment and relationships.
- AI is most valuable in insurance when it removes low-value, manual work and gives professionals more time for decision-making and customer experience.
- Insurers that block AI entirely risk disengaging newer talent who already expect to use it as part of their work.
- Responsible AI adoption in insurance requires clear guardrails, strong security practices, and human accountability for outcomes.
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