How one data infrastructure company moved from event-based training to continuous, AI-driven skill development across hundreds of sellers.

Sales enablement is changing fast. The old model of quarterly training sessions, one-size-fits-all onboarding, and "check-the-box" certifications can't keep up with the pace that modern revenue teams need to operate at. Reps forget what they've learned within days. Managers don't have the bandwidth to run roleplay with every rep on their team. And enablement leaders are stuck measuring attendance instead of actual behavior change.

At FullyRamped, we recently hosted our first customer webinar with Cribl, featuring Andy Hershey, VP of Strategic Sales, and Betsy McCausland, Revenue Enablement Manager. They shared how Cribl has rolled out AI-powered roleplay across hundreds of reps — from regional sales managers and SDRs to solutions engineers — and the impact it's had on their enablement strategy, rep performance, and sales leadership.

Want the full conversation? Watch the on-demand webinar here. Below are the biggest takeaways.

The Shift from Event-Based Training to Continuous Enablement

Betsy described a fundamental shift she's seen over the last few years: enablement has moved from being content-driven to ecosystem-driven, and from event-based to just-in-time.

Instead of relying on stand-and-deliver training sessions and hoping reps retain the material, Cribl's enablement team now focuses on delivering contextual, on-demand reinforcement. That means skill practice before a big call, messaging refreshers tied to real opportunities, and structured scenarios that reps can access when they need them — not just when a training is scheduled.

As Betsy put it, attendance doesn't translate to behavior change. Reps can sit through a session and still struggle to apply the skill in a real customer conversation. The future of enablement isn't more training — it's practical application and smarter reinforcement.

Why Cribl Chose AI Roleplay

When Cribl started evaluating AI roleplay tools, they had two clear problems to solve.

First, reps weren't getting enough practice. Skills like discovery, objection handling, and messaging require repetition to master. But in practice, reps were only exercising those skills in live, high-stakes customer conversations — the worst possible time to be learning on the job.

Second, traditional roleplay doesn't scale. Cribl could run effective manager-led roleplay certifications, but each one consumed 6 to 10 hours of leadership time. That wasn't realistic or sustainable, especially as the team grew. They needed a way to create a safe, repeatable practice environment that didn't depend on manager availability — while still freeing managers to focus on high-impact coaching.

FullyRamped gave them exactly that: a platform where reps can get unlimited at-bats against realistic sales scenarios, on their own time, with AI-powered coaching and scoring built in.

Sales Leadership Buy-In Is Non-Negotiable

One of the strongest themes from the webinar was the importance of top-down sales leadership support. Betsy's advice to enablement leaders evaluating AI roleplay tools: treat this less like a software purchase and more like a change management initiative.

Her recommendations for a successful rollout:

• Bring sellers and sales leaders into the evaluation. Let them pressure-test the scenarios and participate in POVs. If they're involved early, adoption follows naturally.

• Get executive sales sponsorship. Sales leaders are significantly more effective at driving adoption than enablement teams pushing it alone.

• Find a vendor partner who's leaned in. AI is evolving rapidly. An engaged, responsive customer success relationship matters more than a feature checklist.

• Don't underestimate conversational realism. Reps need to lose themselves in the simulation. If the AI feels robotic or has unnatural pauses, engagement drops off fast.

Andy echoed this from the sales leader perspective. He views enablement and RevOps as critical partners to his success — not a shared services team. His advice to other sales leaders: don't wait for enablement to guess what you need. Be prescriptive. Tell them what the field needs, and partner with them to deliver it.

Real-World Use Cases: From Mutual Action Plans to Legal Negotiations

Cribl's use of FullyRamped has expanded well beyond basic cold-call practice. Some of the scenarios they've deployed include:

• Mutual Action Plans (MAPs): After enablement introduced MAP best practices, reps immediately practiced positioning them with a buyer in a FullyRamped simulation — reinforcing the skill while it was fresh.

• Legal negotiations: Cribl's enterprise deals involve complex contract discussions around AI liability and indemnification. FullyRamped simulations let sellers practice positioning paper and terms before high-stakes negotiations.

• Force Management methodology: After investing in Force Management training, Cribl built roleplay scenarios around specific techniques — including "trap-setting questions," one of the most valuable but challenging skills in the framework. The AI roleplay provides expert-level guidance that reps can't always get from a manager who's still learning the methodology themselves.

• Observability discovery calls: Even Andy, a non-technical sales leader, used FullyRamped to practice and scored well — reinforcing that effective selling is about asking the right questions and identifying pain, not being a technical expert on every product feature.

This range of use cases underscores a key insight: AI roleplay isn't just for SDRs or cold calling. Some of the deepest engagement comes from tenured, experienced sellers who are serious about honing their craft.

The Data Changes Everything

One of the most impactful changes Betsy highlighted was the leap from measuring attendance to measuring actual skill development.

With FullyRamped's scorecards and AI coaching, Cribl's enablement team can now see exactly where reps are excelling, where they're struggling, and where they need more coaching — across the entire org. That's a fundamentally different signal than "who showed up to the training."

Andy added that the platform has created a healthy competitive dynamic. Reps retake simulations to improve their scores. They prepare more thoroughly because they know the roleplay is recorded and scored. The prep work itself — reviewing content, building an outline, refreshing on messaging — becomes an enablement moment on top of the roleplay.

As Andy put it: the roleplay is valuable in itself, but the reinforcing and pre-work that reps do to prepare is icing on the cake.

Finding the Right Cadence

For enablement leaders wondering how often to run AI roleplays, Cribl's approach is straightforward:

• For tenured reps: Once a month, focused on a specific situational scenario, integrated into the team's existing operating cadence (12-week planning cycles, forecast rhythms, etc.).

• For new hires in onboarding: Much higher frequency — five to seven roleplays per month during the first few months, covering product knowledge, sales cycle, and messaging fundamentals.

The key, both Andy and Betsy emphasized, is being thoughtful about not overwhelming the field. Publish the cadence in advance, set clear expectations, and make sure the roleplay topics align with the team's top priorities for the quarter.

What's Next: Multi-Persona Roleplay, AI Twins, and Rep-Driven Enablement

Looking ahead, the Cribl team is most excited about several upcoming FullyRamped capabilities:

• Multi-persona roleplays: Simulating calls with multiple stakeholders on the other side of the table — a much more realistic scenario for enterprise sales.

• AI Twins and Gong integration: Creating AI personas based on real call recordings, enabling reps to practice against scenarios pulled directly from their pipeline.

• Dr. Deal: Deal-specific roleplay and individual skill development tied to the opportunities reps are actively working.

• Multi-language support: Expanding roleplay into German, French, Spanish, and other languages as Cribl grows globally.

The overarching theme is rep-driven enablement — giving sellers the tools to self-enable, practice on their own terms, and close the gap between learning a skill and applying it in the field.

Be Elite

Andy closed the webinar with a phrase his strategic sales team lives by: be elite. Not that they are elite — but that they aspire to be. And the way you get there is by practicing, competing, and leveraging every tool at your disposal to sharpen your skills.

AI-powered roleplay isn't a nice-to-have anymore. For teams like Cribl that are serious about building a world-class sales organization, it's becoming a core part of how they develop, reinforce, and measure seller performance.

Watch the full webinar on demand to hear directly from Andy and Betsy, or book a demo with FullyRamped to see how AI roleplay can transform your enablement program.