What if the fastest path to growth isn’t finding new customers, but reactivating the ones you already had? In this episode, Dan Pfister shares the surprising math behind winback programs, why dormant accounts are a hidden revenue engine, and how enterprise teams can turn trust and tribal knowledge into a repeatable expansion strategy. Packed with research, practical examples, and sharp insights, this one’s a blueprint for account growth in 2025.

Key takeaways:

• Why winback and reactivation are underutilized in enterprise account strategy
• 26% average return rate of lost customers (up to 31% per Harvard study)
• Reactivated customers have 2x lifetime value
• Cost of winback is drastically lower (as low as $5k per SMB campaign)
• Peak-end rule & Pratt-Fall effect: psychological science behind winback success
• Strategic segmentation: not all “lost” accounts are the same—some are dormant
• Winback Propensity Model and Customer Journey Mapping for program design
• Internal referrals as the most powerful path to account expansion
• Using trust, tribal knowledge, and insights to reactivate and expand accounts
• Tactical advice: how to build a scalable, repeatable program inside large enterprises

Guest:
Dan Pfister, Founder of WinBack Labs
LinkedIn

Enterprise selling isn’t solo—it’s a team sport. In this episode, Fred Diamond unpacks what makes today’s best account teams succeed: structured collaboration, specific problem-solving, and a leadership mindset. From the four E’s of sales effectiveness to insights on AI adoption, Fred shares practical frameworks and real-world stories from top companies. If you lead—or sell into—strategic accounts, this episode will change how you think about team performance and customer engagement.

Guest:
Fred Diamond, Co-founder, Institute for Effective Professional Selling (IEPS)
Host of Sales Game Changers Podcast

Main points covered:

• Why most enterprise sales teams struggle with engagement and collaboration
• The Four E’s of sales effectiveness: Engage, Empower, Elevate, and Execute
• Why account team performance depends on internal collaboration—not just individual skill
• The shift from general sales training to specific customer problem solving
• How community-based coaching models (like IEPS groups) outperform generic enablement
• Why remote work risks disengagement, and what leaders must do to fix it
• What elite sales professionals do differently to get the next meeting
• AI in sales: why adoption is low today—but poised to transform how teams prepare and communicate
• How companies should design AI into sales workflows, not just license tools
• What great enterprise sellers really want: support, visibility, and pathways to grow

In this episode, Dave Irwin sits down with Paul Butterfield, CEO of Revenue Flywheel Group, to unpack what it really means to enable enterprise teams around the customer’s journey.

Paul shares insights from decades in sales leadership and enablement, showing why traditional demo-first approaches fail and how the best account teams co-create value with their buyers…well before a formal initiative even exists.

From stakeholder mapping and discovery depth to trust-building, Paul makes the case for a shift toward insight-driven selling that prioritizes customer impact over pitch decks.

Guest:
Paul Butterfield, CEO, Revenue Flywheel Group
https://www.linkedin.com/in/paulbutterfield/

Key Points:
- Why sales enablement must expand across the entire customer journey
- The power of insight-driven discovery vs. check-the-box qualification
- How to move from selling a product to enabling outcomes
- Why most messaging fails: it's about features, not the customer's reality
- Strategies for engaging multiple stakeholders with tailored discovery
- How to co-create initiatives with buyers vs. reacting to defined RFPs
- The importance of stakeholder-specific impact and how to reflect it back
- Using “Opportunity Qualification Meetings” to align buying groups internally
- How to lead with business acumen, even if you’re not the domain expert
- Why post-sale visibility and implementation planning builds pre-sale trust
- A three-part framework for buyer trust: Authenticity, Competence, Empowerment