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LIVE WEBINAR

Reskilling for AI: Strategies to Retrain and Retain Insurance Employees 

March 19, 2026  |  2pm ET  |  45 minutes

 

AI is changing how work gets done across insurance operations. As repetitive and preparation-heavy tasks become automated, day-to-day responsibilities are shifting toward review, exception handling, judgment, and stronger customer interaction. This is not just a technology shift. It requires clear decisions about roles, practical workflow adjustments, and steady leadership so employees understand what is changing and what is expected of them. 

This session focuses on straightforward workforce strategies that help organizations manage that transition well. We will discuss how to identify which workflows are likely to change, define future responsibilities early, retrain employees for new expectations, and communicate in ways that reduce uncertainty. With the right approach, organizations can guide workforce transition in a structured way, protect institutional knowledge, build trust across teams, and support long-term adoption of AI throughout the business. 

 

Register to learn:

  • Which workflows are most likely to change as AI enters insurance operations
  • How responsibilities and roles evolve as AI changes workflows
  • What workforce readiness and retraining may look like as AI adoption expands
  • The role of pilot programs and internal communication in building confidence and internal champions
  • What organizations are measuring to understand the operational and workforce impact of AI 

Speaker

Diane Brassard
Diane Brassard
Head of Education and Advocacy

With over 30 years of experience spanning claims, underwriting, automation, and operational leadership, Diane Brassard serves as Head of Education and Advocacy at Roots. In this role, Diane bridges decades of insurance expertise with cutting-edge AI solutions—helping organizations understand, embrace, and implement intelligent automation to transform how insurance gets done. 

Before joining Roots, Diane held senior roles at WR Berkley—Regional Shared Services and Berkley Mid-Atlantic Insurance Group, where she led stakeholder engagement, offshore initiatives, and underwriting operations; she also held leadership roles at Colony Specialty (Argo Group), including oversight of Marine business functions, and spent over two decades at The Main Street America Group driving improvements in claims, training, and technology to enhance service quality and support growth. 

Reskilling for AI: Strategies to Retrain and Retain Insurance Employees

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