Kelsey
Rich
VP Digital Product at Employers Insurance Group
"Leading Your Team Into the AI Era: Building the Culture, Ethics, and Courage to Transform"
"Leading Your Team Into the AI Era: Building the Culture, Ethics, and Courage to Transform"
Tue May 12 - 1:20 PM EDT/New York (See in local time)
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05/12/2026 1:20 PM
05/12/2026 01:40 PM
America/New_York
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"Leading Your Team Into the AI Era: Building the Culture, Ethics, and Courage to Transform"
#WTGC2026
"Leading Your Team Into the AI Era: Building the Culture, Ethics, and Courage to Transform"
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"Leading Your Team Into the AI Era: Building the Culture, Ethics, and Courage to Transform"
"Leading Your Team Into the AI Era: Building the Culture, Ethics, and Courage to Transform"
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Session: Leading Your Team Into the AI Era: Building the Culture, Ethics, and Courage to Transform
Your team is scared. They've read the headlines. They've seen the demos. They're wondering if AI is coming for their jobs, and they're looking to you for answers you might not have yet.This is the leadership challenge of our generation: How do you guide your team through a technological transformation when the ground is shifting beneath everyone's feet? How do you create psychological safety to experiment with tools that feel threatening? How do you build an ethical framework that empowers rather than restricts? And how do you help people see AI as a partner that amplifies their value rather than a replacement waiting in the wings?
As VP of Digital Product at a workers' compensation insurance company, I've been navigating this transition with my team in real time. We've built AI ethics guidelines grounded in six core principles: inclusivity, equity, accountability, safety, human centricity, and sustainability. We've created permission structures that encourage experimentation. We've run workshops where product managers experienced AI as a creative partner, building product briefs, story maps, and working prototypes in hours instead of weeks. And we've had hard, honest conversations about fear, relevance, and what it means to be valuable in an AI-augmented world.
This session shares the leadership playbook I wish I'd had when we started: practical frameworks for leading cultural change around AI adoption
Key Takeaways
- Ideas for hands-on experiences that shift mindset from fear to partnership
- Conversation templates for addressing team anxiety about AI and job security
- A framework for building AI ethics and usage guidelines grounded in six core principles
- A checklist for assessing your team's AI adoption readiness and culture
- Strategies for positioning yourself as an AI-fluent leader to accelerate your career
Bio
Kelsey Rich is VP of Digital Product at EMPLOYERS, a workers' compensation insurance company, where she leads product managers and designers across distribution, customer experience, and claims platforms. She is passionate about building product talent and creating cultures where teams can thrive through technological change.Throughout her 15+ year career spanning Pinnacol Assurance/Cake Insure, Intuit, and EMPLOYERS, Kelsey has consistently led teams through industry-transforming changes, from digital transformation in traditional financial services to building entirely new business models in insurtech.
At EMPLOYERS, Kelsey has built a product maturity program focused on developing strategic thinking, customer empathy, and AI fluency. Her team is actively navigating the AI transformation, experimenting with AI-powered tools for product development, establishing ethics guidelines grounded in inclusivity, equity, accountability, safety, human centricity, and sustainability, and redefining what product work looks like in an AI-augmented world.
Kelsey recently completed credentials in Product Strategy and AI Business Strategy from Northwestern Kellogg's Executive Education program. Prior to EMPLOYERS, she built and scaled an MGA at Intuit QuickBooks Insurance. Her deep expertise in leading teams through digital transformation in traditional industries positions her uniquely to help others navigate the AI transition.
