Why Sales Training Fails And How AI is Fixing It | Ivy Holt

In this episode of Revenue Insights, host Guy Rubin sits down with Ivy Holt, Head of Global Revenue Enablement at PagerDuty, to explore the evolving role of enablement in driving sales success. Ivy shares insights on the distinction between revenue operations and enablement, the challenges of measuring effectiveness, and the impact of AI and remote work on modern sales training.

She highlights the importance of behavior change, strategic alignment, and leveraging technology while maintaining strong human connections throughout the revenue lifecycle.

With over 18 years of experience in sales, operations, and strategy, Ivy has led transformative initiatives at Red Hat, Pendo, and PagerDuty. She specializes in aligning global teams, scaling enterprise sales, and shifting organizations from transactional selling to strategic partnerships.

This episode offers valuable takeaways for sales leaders and enablement professionals looking to optimize team performance and drive measurable revenue growth.

• Ivy Holt on LinkedIn
• PagerDuty website
• Guy Rubin on LinkedIn
• Ebsta Revenue Insights Newsletter

Time Stamps:

• [00:00] Intro: Defining Revenue Enablement
• [01:27] Career Journey in Sales
• [04:41] Aligning Teams and Messaging
• [08:37] Revenue Ops vs Enablement
• [13:21] Full Revenue Lifecycle
• [17:20] Strategic C-Suite Relationships
• [21:36] Replicating Top Performers
• [24:12] Measuring Enablement Success
• [31:01] Technology’s Evolving Role
• [33:06] Virtual vs In-Person Training
• [37:27] Key Sales Takeaways

Highlights of Why Sales Training Fails:

The Translation Layer in Enablement

Ivy highlights the need for a “translation layer” that simplifies complex information from product, IT, legal, and sales teams into clear, actionable guidance. Enablement teams can streamline communication by establishing advisory councils and regular stakeholder meetings. This ensures sales teams focus on revenue-generating activities rather than internal complexity.

Aligning Revenue Across the Lifecycle

Revenue enablement must support the entire customer journey, from pre-sales to renewals. Consistent messaging across teams prevents mismatches in customer expectations. As enterprise sales evolve, enablement helps teams handle both single-seat deals and C-suite engagements.

Systematizing Top Performer Success

Successful enablement programs identify and document winning sales behaviors through playbooks and tools like Gong. Breaking down processes by sales stage ensures repeatability, while gradual implementation supports adoption.

Technology as an Enablement Asset

Modern AI tools and call recordings now serve as coaching aids rather than surveillance. Used effectively, they simplify workflow, reinforce best practices, and drive behavioral change without adding administrative burden.

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