Training That Works
Training That Works is the podcast for sales leaders who are tired of programs that don't move the number. Host Rustin Schroeder sits down with directors, VPs, and Chief Learning Officers to unpack what actually drives performance — from onboarding and sales enablement to leadership development and coaching at scale.
Every episode is a real conversation with someone who has built and run training inside companies you know. No theory, no buzzwords, no recycled frameworks. Just the strategies, mistakes, and breakthroughs that separate training that checks a box from training that changes results.
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Training That Works
Signal Through Noise with Ian Westbrook
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Most sales training quietly drifts away from the job it is supposed to teach.
In this episode of Training That Works, Rustin Schroeder talks with Ian Westbrook, Head of Go-to-Market Enablement at Canva, about finding the signal through the noise when product velocity never slows down.
Ian has an unfair advantage most enablement leaders do not. He carried a bag as an enterprise seller for years before he ever built a training program, so he knows exactly where training loses the room. At Canva, where new products and features ship at a relentless pace, his job is to cut signal through the noise and keep sellers focused on the customer's broken workflows instead of drowning them in feature lists. Listen and you walk away with a sharper way to make enablement actually change behavior.
A mid-career move into an unfamiliar craft became the foundation of everything he does now. Ian almost left sales to become a data scientist, then walked through a different door into enablement at the Oracle Marketing Cloud. The seller became the systems architect, eventually building the first go-to-market process strategy and design organization at DocuSign. Along the way he picked up UX research, data analytics, and a systems view that treats training as one component inside a much larger machine of incentives and accountability.
Here is the part most leaders will not say out loud. You keep buying tools and building courses, and the change still slides back to where it started by the next quarter. Ian draws a hard line between training that sounds good and training that actually sticks, and his answer for the difference is blunt. Buy-in and accountability are the primary predictors of whether anything lasts, and training only supports what those structures already hold in place. In this episode you will learn his six-step framework for large-scale change, why "process first" beats another tool in your stack, how conversation intelligence and AI role play are reshaping coaching, and how to keep training from drifting into an abstraction nobody connects to their actual job.
Business leaders, sales enablement teams, and go-to-market executives will find a practical playbook for building training that drives adoption and keeps teams focused on what actually moves the business forward.
Press play before you green-light another tool or another rollout.
Ian Westbrook is Head of Go-to-Market Enablement at Canva and previously built the first go-to-market process strategy and design organization at DocuSign.
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