Go To Masters Show

Robby Halford (Momentive Software) on Why Enablement Needs the CRO, Ramp Design & AI Coaching

June 27, 2026·48 min
Episode Description from the Publisher

Most ramp programs are just bad instructional design dressed up as onboarding. A week of PowerPoints, a parade of decks, and then we throw new sellers on the floor and hope. Robby Halford has watched this break sales teams for over a decade — and built something different.Robby is VP of Go-to-Market Performance at Momentive Software, where he oversees enablement, business development, marketing operations, and sales operations. He started his career as a middle school English teacher, spent six years carrying a bag (and made President's Club in his first full year), and is finishing a doctorate in curriculum and instruction. He brings the seriousness of an academic and the empathy of a former seller to every program he builds.He joins GoToMasters to argue that enablement is not a slide-making team. It's the execution wing of every strategic decision a leadership team makes, and the function only works when it has a direct seat at the CRO's table. He breaks down why he pays new sellers to learn for a full month before they touch a quota, why CSMs are the most under-enabled team in most orgs, why throwing more enablement at a problem rarely fixes it, and why AI feedback often lands better than manager feedback — because it has no feelings to hurt.If you're building an enablement function, designing a ramp program, or trying to elevate learning into a revenue-generating activity, this one's worth your time.

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