Sales and customer success teams today face an ongoing challenge: how to engage buyers effectively, drive urgency, and execute sales strategies with precision. In a recent webinar, Elay Cohen Cohen, CEO of SalesHood, sat down with Amy Pence, Director of Enablement at DISQO, to explore how AI-powered role-playing is revolutionizing sales performance.
Amy, a seasoned sales enablement leader, shared her insights on how DISQO has successfully integrated AI role-playing into their training strategy, helping sellers build confidence, improve execution, and ultimately close more deals. Amy shared details on a storytelling initiative that started at their sales kickoff and gained momentum post-kickoff with AI role playing.
Here’s what we learned.
The Power of Storytelling in Sales
Storytelling is one of the oldest and most effective ways to communicate. In a sales context, it serves multiple purposes:
- Building trust – A well-told story creates credibility and resonates with buyers.
- Combating discovery fatigue – Instead of overwhelming buyers with endless questions, storytelling can validate pain points and show a clear path to resolution.
Driving urgency – A strong story helps buyers see the value of acting now, rather than later.
“Our ultimate goal was to create that ‘I want that’ moment,” Amy explained. “Storytelling is not just about sharing information—it’s about making the buyer feel the impact.”
To embed storytelling into the sales process, DISQO introduced a simple five-step framework:
- Start with a punchline – Capture attention with an impactful opening.
- Provide context – Explain the challenge or pain point.
- Take them through the journey – Show how the problem was solved.
- Highlight the results – Demonstrate the measurable impact.
- End with a call to action – Invite engagement and next steps.
By equipping sellers with structured yet adaptable storytelling skills, DISQO ensured that sales conversations were more engaging and results-driven.
AI Role-Playing: The Future of Sales Coaching
To reinforce storytelling skills, DISQO turned to AI-driven role-playing. AI allows reps to practice in a risk-free environment, receive real-time feedback, and refine their messaging before going into live sales conversations.
Amy described how the adoption of AI role-playing evolved at DISQO:
- Step 1: Learning the framework – Reps first practiced storytelling in a structured workshop.
- Step 2: AI coaching – Sellers used an AI coach to refine their storytelling, receive a score, and iterate.
- Step 3: AI role-playing – Reps engaged in simulated conversations where AI responded dynamically, asked unexpected questions, and provided feedback on objection handling.
At first, some reps were hesitant. “It was weird at first,” Amy admitted. “But once they started engaging with the AI, it became natural. The AI threw in unexpected questions, making it feel real.”
One of the biggest benefits? Reps practiced their storytelling an average of five to six times per session. The competitive nature of improving AI scores led to better preparation and stronger performance in real sales interactions.
Scaling Sales Enablement with AI
A major advantage of AI coaching is scalability. As a team of one, Amy needed a way to ensure consistent coaching across the entire sales org without consuming all her time. AI made that possible.
“AI helps make preparation so much more efficient and gives people time back to focus on the important selling activities,” Amy said. “It’s about giving our sellers the confidence to have better conversations.”
Managers also benefited from AI-driven coaching. Instead of manually reviewing every rep’s performance, they could leverage AI-generated insights to identify strengths, pinpoint areas for improvement, and tailor coaching sessions accordingly.
Key Takeaways
- Storytelling is a must-have skill for modern sellers – It combats discovery fatigue, builds credibility, and drives urgency.
- AI role-playing accelerates learning and confidence – Reps can practice in a low-pressure environment and refine their skills with real-time AI feedback.
- AI enables scalability in sales enablement – It frees up time for both sellers and enablement leaders while ensuring consistent training at scale.
What’s Next?
The future of sales enablement is AI-driven. As Amy put it, “Super flexible, super approachable—that’s what makes SalesHood’s AI role-playing different.”
Imagine a world where every seller has a personal AI assistant that preps them for meetings, helps them refine their messaging, and ensures they’re always ready to engage buyers effectively. That future isn’t far off.
Want to experience AI role-playing for yourself? Book a demo with SalesHood today and see how AI can transform your sales team.
