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Cait
Stewart
GTM Onboarding Manager
Pigment
Cait leads the strategy, design, and execution of onboarding and early-tenure development across the GTM organization. Her focus is on accelerating ramp time, improving new hire productivity, and fostering a strong sense of connection and belonging. She is dedicated to delivering consistent, high-quality enablement experiences that drive measurable business impact.
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12 November 2026 11:30 - 12:00
Manager muscle memory: Role play and AI coaches to scale beyond book to behaviour
Gallup’s 2026 State of the Global Workplace report makes a compelling argument: “Few managers have natural management talent, and many have not received the training they need to successfully coach teams and individuals toward high performance. … AI tools [could] provide real-time, personalized manager advice grounded in the best management science... a game-changer for the world’s workplace.” When few managers have natural management talent, and FEWER actually receive training on management, what are we left with to solve this problem? Forget book clubs or standalone workshops! Instead, we anticipated the hard conversations before they happened, fed our AI role play the award-winning playbooks, and then served up on-demand coaching tools made possible by a custom GPT and Claude Skill. In this session, you’ll see how it worked, what the early signals show (and what’s too early to call), and what we’d do differently. You’ll leave with: - A repeatable approach geared specifically for managers that score against a credible framework - Ideas for using a GPT or Claude Skill as an always-available managerial coach - A way to measure managerial development beyond completion rates and surveys