#1 Best Results#1 Most Implementable#1 Highest User AdoptionFree ReportThe 2026 AI Roleplay Readiness Report
What 15,000 AI roleplays reveal about where customer-facing teams break down in live conversations, what top performers do differently, and what regular practice changes for ramp, coaching, and customer outcomes.
Three Findings From the Report
From Outdoo's analysis of 15,000+ AI roleplays across sales, customer success, support, and field teams.
Eight Chapters on Building Readiness That Shows Up
Why training rarely survives a live conversation, what the simulation data shows, and how to measure readiness before it shows up in pipeline or churn.
- The readiness gap between training and real conversations
- The five skill gaps: discovery, objections, differentiation, confidence, and empathy
- What top performers do differently under pressure
- Benchmarks for ramp, coaching time, pipeline, and CSAT
- Case studies from sales, customer success, frontline, and L&D teams
- How to measure readiness and model the ROI
Built for the People Who Own Readiness
Sales Leaders and CROs
Benchmarks for ramp, qualified pipeline, and late-stage confidence, and the behaviors that predict them.
Enablement and L&D
A step-by-step plan to roll out AI roleplay, certify skills, and report readiness before it reaches the pipeline.
Customer Success and Support
Where tone and empathy break down in escalations and renewals, and what practice changes for CSAT.
Frequently Asked Questions
About the 2026 AI Roleplay Readiness Report.
Is the AI Roleplay Readiness Report free?
Yes. Enter your name and work email and the 53-page PDF opens right away.
What data is the report based on?
Outdoo AI's analysis of more than 15,000 AI roleplays across sales, customer success, support, and field teams, alongside published research on training and skill retention.
Who should read it?
Sales leaders, enablement and L&D teams, and customer success and support leaders who own how ready their teams are for live conversations.
Do I need to talk to sales to get it?
No. The download is instant. If you want to see AI roleplay on your own team's calls, you can book a 30-minute demo separately.
Want to See It on Your Team's Calls?
Get the report above, or book a 30-minute walkthrough built around your own calls and playbooks.
