Courtney Callesto

Global Learning & Enablement Leader | 4,000+ Employees Supported | Driving Performance Through Scalable Training

Keeper Security, Inc.ex-eBayex-South Mountain Community Church

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I build enablement programs that actually change how teams perform. Over the past 10+ years at eBay, I’ve led onboarding and enablement strategy supporting 4,000+ customer-facing employees across global partner organizations.

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My focus has always been the same: helping teams ramp faster, perform consistently, and confidently adopt new tools and workflows. Some of the outcomes I’ve driven: • Improved time-to-productivity by 20–30% across distributed teams • Led adoption of new tools and workflows with 80%+ adoption in under 90 days • Built scalable learning systems that reduced reliance on live training by 30–40% I’ve spent most of my career working at the intersection of learning, operations, and performance—partnering closely with leaders to identify gaps and build practical, scalable solutions. More recently, that work has expanded into supporting teams with AI tools—helping them move from awareness to real, day-to-day use in their workflows. I’m especially interested in roles focused on: • Customer Support Enablement • Onboarding & Performance Programs • Scalable Learning Systems • AI & Tool Adoption