Michael Phelan joins Dave Irwin to unpack the hidden drivers of successful enterprise engagement. From customer interviews to competitive benchmarks, Phelan reveals what actually gets attention in the boardroom—and how smart sellers can become magnets for internal buy-in. This episode is a masterclass in landing big accounts and unlocking massive expansion without ever leading with your product. If you want to become the analyst your customers trust, this one's for you.

Guest: Michael Phelan, Founder & Principal Go to Market Pros

Key points:

• Why personalization fails and insight succeeds in enterprise selling
• The “Jobs to Be Done” framework for identifying customer needs
• How best-in-class competitor benchmarks create internal urgency
• Becoming a trusted analyst and source of insight (not just a seller)
• Research-backed ways to drive expansion across large accounts
• Practical examples: how companies like Target and AT&T respond to insight-led engagement
• How to engage earlier in the buyer’s journey and shape the pursuit
• Creating before-and-after moments that visualize value
• Why sellers must spark internal collaboration to win expansion deals

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