In the world of sales, hitting quota is the ultimate measure of success. But what if your team could achieve a 90% quota attainment rate year after year? Sounds impossible? Not according to Taylor Jurgens, VP of Enablement at Ushur, who shared during SellMeThisPen podcast how he helped build Auth0's enablement program from scratch and maintained this impressive benchmark even through the Okta acquisition.
The key? An approach to sales roleplays that transformed how new reps were onboarded and equipped for success. In this article, we'll analyze why most companies get roleplays wrong and the step-by-step formula that Taylor used to create consistent sales excellence.
Here's a reality check: most companies don't do roleplays at all. And those that do often implement them incorrectly, leading to poor results and frustration. The most common mistakes include:
These issues create a cycle where sales teams never truly master the fundamental skills needed for consistent success. But Taylor's approach at Auth0 broke this cycle.
The first crucial element in Taylor's roleplay revolution was ensuring complete leadership participation. At Auth0, this wasn't optional – it was mandatory.
Why was this so important? Because leaders needed to experience firsthand what their reps were going through and understand the value being created.
As Taylor explains:
"Sales leaders are always the first people to say, 'well, I don't want my people doing [roleplays]' or 'it takes too much time'.
BUT by the time they got through it themselves, they were like, 'actually, can we spend more time doing that?'"
This transformation turned potential obstacles into the program's biggest advocates. When leaders recognized the value of structured practice, they championed it throughout the organization.
The second breakthrough in Taylor's approach was a complete reimagining of the onboarding process. When new reps joined Auth0, their first 30 days were dedicated to pure enablement:
Instead, new reps focused almost exclusively on roleplays with one primary objective: mastering discovery.
This dedicated focus on foundational skills – particularly discovery – allowed reps to build confidence and competence before facing real prospects. They learned how to ask effective questions, uncover genuine pain points, and construct compelling value propositions without the pressure of immediate quota expectations.
The results of this approach speak for themselves:
By investing heavily in upfront enablement and structured practice, Auth0 created a sales organization that consistently outperformed industry benchmarks.
As Auth0 grew from a startup to an enterprise (eventually leading to the Okta acquisition), Taylor faced a new challenge: how to scale this high-touch enablement program as the team expanded from 20 reps to 160 reps per bootcamp.
The math became daunting:
This scaling challenge required a creative solution that maintained the core principles while adapting to new realities.
To solve the scaling problem, Taylor's team broke down the roleplay sessions into shorter, more focused segments that targeted specific skills:
This modular approach allowed for more efficient coaching while maintaining the quality of the practice. Instead of trying to master everything at once, reps could build competence in individual skills that combined to create overall sales excellence.
Taylor emphasizes that today's technology offers even more powerful scaling options:
"If you're not using AI in 90% of what you do, you're not doing it right. It's like an extra head count on your team, at least."
Modern AI can now help scale roleplay sessions and sales coaching. Tools like SellMeThisPen allow even the largest sales organizations to maintain the quality and consistency of their enablement programs without sacrificing personalization or effectiveness.
Based on Taylor's experience building Auth0's world-class sales organization, here's the complete formula for roleplay success:
As you consider your own sales enablement strategy, ask yourself: Are you investing enough in structured practice? Do your leaders actively participate in and champion roleplay sessions? Are you leveraging modern AI tools to scale your coaching efforts? The answers to these questions could determine whether your team struggles to meet quota or consistently exceeds expectations.
In this episode of SellMeThisPen Podcast, Michael and Taylor discuss the transformative power of effective roleplay programs in sales enablement. They explore why most companies get roleplays wrong, how to secure genuine leadership buy-in, and the step-by-step process Auth0 used to achieve 90% quota attainment across their sales organization. Taylor also shares insights on scaling enablement programs as teams grow and the role of AI in modern sales coaching.
Taylor Jurgens is the VP of Enablement at Ushur who previously helped build Auth0's enablement program from scratch and guided the team through the Okta acquisition. Under his enablement leadership, an impressive 90% of sales reps consistently hit their quota every year, with fully ramped reps in just 60 days and sales cycles under 90 days.
