The Leadership Gap in the AI Era
We'll cover why AI adoption is exposing a leadership readiness gap with Cal Cooper from Vendasta and Sarah Sheehan, CEO at Bravely.
🗓️ Thursday, September 24, 2026
🕛 12:00 PM ET
⌛ 60 minutes
AI is moving quickly, and most organizations are still figuring out where it can create real value, how fast to adopt it, and what responsible implementation should look like...
That uncertainty is both a technology and leadership challenge.
As companies experiment with new tools and new ways of working, AI is exposing weaknesses that already exist inside organizations: unclear decision-making, outdated processes, siloed teams, uneven manager capability, and cultures that struggle with ambiguity and change. Layering AI onto those foundations doesn’t automatically create transformation. In some cases, it simply accelerates the dysfunction that was already there.
The challenge for leaders who are being asked to quickly adopt AI is building a strategy that enables their people to make good decisions while the technology, use cases, and rules of work are still evolving.
In this conversation, we’ll explore the growing gap between AI adoption and leadership readiness and what it means for the way organizations develop their people. We’ll look at how AI is changing the way work gets organized, decisions get made, expertise gets distributed, and teams navigate constant change.
We’ll also tackle a bigger question: What does great leadership look like in a workplace that is still being reshaped by AI?
A 60-minute live session. Free to register.
Recording available if you can't make it live.
Who Should Attend
What We'll Cover
- Why AI can amplify organizational dysfunction as easily as it can improve productivity
- Why AI adoption is an operating model and leadership challenge, not just a technology rollout
- How leaders need to evolve as work, decision-making, and expertise become more distributed
- The leadership capabilities that matter most in an AI-enabled workplace
- How HR can build those capabilities while the technology and ways of working are still evolving
About Your Host
Sarah Sheehan
Co-Founder and CEO, Bravely
Sarah has spent the last decade building Bravely into a coaching platform trusted by progressive companies like the NBA, Etsy, and Pinterest. She's spent the last year talking with People leaders about what great leadershp looks like as AI continues to reshape the workplace.
She'll be joined by Cal Cooper from Vendasta who will provide her first hand experience and valuable insight to explore how leaders can evolve as work, decision-making, and expertise become more distributed.
Calista Cooper
Head of Operations & AI Transformation,Vendasta
Cal Cooper is Head of Operations and AI Transformation at Vendasta, where she leads the company's shift to an AI-first operating model. She's especially focused on growing AI capability across the organization: designing progression pathways that take people from AI literacy to confident, responsible building, with clear guardrails around the innovation. Her broader work in operations, learning, and enablement (including Vendasta's AI-powered Doc Ops system) all supports this same goal: helping teams build sustainably and responsibly with AI.
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