How a Fortune 100 Enterprise Tech Company Certified 2,000 CSMs During Virtual SKO with Yoodli AI Roleplays

TL;DR:

A Fortune 100 enterprise Tech SaaS company (“Company”) used Yoodli’s AI-powered roleplay platform to deliver live, scalable skills training to 2,000 Customer Success Managers and frontline leaders during a virtual Sales Kickoff. Learners practiced nearly 5K roleplays over 430+ hours. The program generated a 4.5/5 CSAT and measurable 5–10% improvements in critical customer conversation skills like “Gracefully Saying No to Customers” and “Handling Business Objections”, while sustaining adoption beyond the event.

4.5 CSAT · 433+ Hours of Practice · 5 – 10% Skill Improvement

Background

During company kickoff, the Company set out to improve CSM confidence and effectiveness in high-stakes customer conversations, including renewals, QBRs, and navigating complex product ecosystems.

The initiative was led by the Enterprise Enablement team and delivered in partnership with external Coaching Partners, with Yoodli providing the AI-powered roleplay technology. Training was conducted virtually across eight 4-hour workshops over 2.5 days, reaching a global, multilingual audience.

The Challenge

The enablement team needed to deliver experiential, skills-based training at massive scale under tight time constraints. Specifically, they needed to:

1. Support 800–900 learners practicing simultaneously within 5–10 minute windows
2. Deliver realistic, contextualized customer simulations aligned to actual CSM workflows
3. Provide automated, nuanced feedback mapped to the company’s proprietary grading rubric
4. Integrate seamlessly into the coaching partner’s LMS and live workshop flow
5. Maintain enterprise-grade reliability and performance during peak global usage

Traditional roleplay and coaching approaches could not meet these requirements

The Solution

Yoodli deployed a customized AI-powered roleplay experience designed specifically for virtual SKO delivery.

Key elements included:

• Contextualized customer conversation simulations based on real enterprise scenarios
• Automated, skill-level feedback aligned to the company’s internal communication rubric
• Multilingual support (English, Spanish, Portuguese, Japanese, and Korean)
• Seamless integration into the coaching partner’s LMS and live facilitation workflow

Learner workflow:

1. CSMs participated in live workshops and breakout groups
2. Learners received links to Yoodli AI roleplays
3. Participants completed AI roleplays and received immediate feedback on foundational skills
4. Groups reconvened to reflect, discuss insights, and apply learnings

This approach enabled private, judgment-free practice while reinforcing peer learning and facilitator-led discussion.

Why Yoodli?

Yoodli was selected because it uniquely combined enterprise-scale performance with realistic, skills-based practice:

• Enabled hundreds of learners to practice simultaneously without facilitator bottlenecks
• Delivered immediate, objective feedback tied to the company’s proprietary rubric
• Supported global, multilingual teams with consistent training quality
• Created a safe environment for learners to build confidence before real customer conversations
• Extended learning beyond the event with on-demand, self-guided practice

The Results

Engagement and Adoption During 4-Hour Workshops

• 2,000 CSMs and frontline managers certified (80% of target audience)
• 4.5 / 5 average CSAT
• 60% of CSMs practiced live, averaging 3 roleplays each
• 90+% of frontline managers practiced live, averaging 6 roleplays each
• 4,800 total roleplays completed
• 430+ hours of recorded roleplay practice (433 hours / 18 days)
• 10%+ of participants continued using Yoodli 2 months post-SKO

Learning Impact

• 5–10% improvement in core customer conversation skills, including:
  • Active Listening
  • Handling Business Objections
  • Gracefully Saying No to Customers
• Deeper, more insightful post-roleplay discussions
• Increased learner confidence and readiness for real customer interactions

Learner Feedback Highlights

• “The interaction felt incredibly real—just like a customer.”
• “The analytics around listening time and filler words were eye-opening.”
• “This was one of the most inclusive training experiences I’ve had here.”
• “It’s a brave new world with AI, it’s definitely given me a lot of food for thought in terms of how to structure my thinking and how to address a customer stakeholder.”
• “I was not expecting such a good level of interaction with the bot and I’m surprised by his answers! He did as good as a customer would!”

Conclusion

This Fortune 100 virtual SKO demonstrated that AI-powered roleplay can deliver measurable, scalable skill development at enterprise scale. By integrating Yoodli into live enablement workflows, the Company transformed SKO from a content-heavy event into a high-impact, practice-driven learning experience, driving strong engagement, measurable skill improvement, and sustained adoption beyond kickoff.