Helen Kupp

Founder, Women Defining AI
Author, How The Future Works

Helen Lee Kupp is the co-founder and creator of Women Defining AI, a community of female leaders tackling the biggest topics of understanding today's generative AI widespread adoption through experimentation, support, and community learning. She takes a practical approach towards helping leaders navigate the biggest changes in work — both from AI/technology, and the flexible/hybrid work revolution.

Helen is also an experienced strategy & operations leader who has helped companies across all stages of growth launch new teams, products, and services. In her former role leading Strategy & Analytics at Slack, she shepherded Slack through the company’s growth from a $75M ARR (primarily credit card self-service product across small teams) to over $1B in enterprise ARR through directly managing launches like the enterprise product & entering international markets. As the co-founder of Future Forum, she combined both data and her own operating experience to advise and coach F500 executives on redesigning work.

She is the co-author of WSJ Bestselling book “How The Future Works: Leading Flexible Teams to Do the Best Work of Their Lives”. Helen brings a unique perspective to how we'll operate in the future by bridging the human component of flexible working alongside the technology component of artificial intelligence creating even greater opportunities to "think & work differently" in a way that benefits more people.

From Fear to Flow: Building AI-Ready Teams Through Hands-On Learning

A workshop with Brian Elliott (Work Forward) and Helen Kupp (Women Defining AI)

The Challenge: While 97% of executives feel urgency around AI adoption, only 8% of employees use AI tools at work daily and fears of job displacement are growing. The gap isn't technical—it's emotional.

The Solution: Team-centered approaches that address fears head-on and create safe spaces for experimentation.

In this interactive workshop, you'll experience firsthand the strategies that successful organizations use to overcome AI adoption barriers. We'll move beyond the hype to explore how AI transforms organizational structures and what it means for responsive leadership in practice.

You'll walk away with:

  • Hands-on experience with AI tools in a collaborative setting

  • A framework for measuring AI maturity across your teams

  • Practical strategies for eliminating "soul-crushing toil" that creates organic momentum

  • Tactical approaches that address the emotional barriers that block adoption

Workshop Format: Some conversation and lots of hands-on experimentation. Bring your laptop! We’ll do some exercises together using AI tools, demonstrating how shared learning accelerates adoption while building the psychological safety essential for organizational transformation.

Perfect for: Leaders seeking to move beyond mandates to meaningful AI integration that enhances both human potential and organizational responsiveness.

No prior AI experience required—just curiosity and willingness to experiment alongside peers.