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

Your internal hero isn’t just a “champion”… they are your best chance at unlocking the rest of the buying center. But ONLY if you know how to elevate them.

In this episode, Dave Irwin sits down with Brynne Tillman, CEO of Social Sales Link, to explore how top-performing account teams use social selling, not to pitch, but to map influence, build trust, and expand from the inside out.

You’ll hear about how to turn one trusted relationship into many, avoid single-threading risks. Brynne also breaks down the right way to ask for introductions (and what not to do), how to become the person your client brags about internally, and the three rules that set elite sellers apart.

Whether you’re managing one strategic account or trying to scale across a territory, this conversation will change how you think about proximity, permission, and growth.

• What social selling is (and what it’s not)
• Using LinkedIn for mapping influence across buyer centers
• The “Hero vs. Champion” mindset
• Avoiding single-threaded relationships
• Elevating internal advocates without pitching
• Tactics for internal and external referrals
• How to be a connector, not just a closer
• Using reverse referrals and soft asks
• 3 rules for landing, expanding, and retaining

Guest:
Brynne Tillman, CEO, Social Sales Link
https://www.linkedin.com/in/brynnetillman
https://socialsaleslink.com

The role of account leaders and insight strategists in driving relevancy, customer engagement, and account growth.

Current State & Problem Identification

• Organizations are stuck in outdated, product-driven playbooks.
• Account teams are overwhelmed, myopic, and misaligned with buyers.
• Significant gaps exist between what buyers need and what sellers provide.

Expert Context

• Brian Shea advises CEOs and revenue leadership teams on overcoming growth barriers.
• Emphasizes the transformation from indirect to direct go-to-market strategies and the importance of aligning teams to new buyer realities.

Key Insights from Conversation

• Importance of understanding buyer-driven change post-pandemic and digital acceleration.
• How outdated approaches cause confidence gaps at all levels (CEOs, leadership teams, frontline sellers).
• The growing complexity of executive buying teams and why traditional product pitches no longer resonate.

Strategic Recommendations

• Elevate conversations to an executive level by deeply understanding customer problems.
• Clearly align capabilities to customer financial metrics and outcomes.
• Differentiate account leaders through executive-level acumen, financial understanding, and trusted advisory presence.
• Adopt a "Batman and Robin" model: Account leaders paired with insight strategists to maximize effectiveness.

Real-world Examples and Success Stories

• A billion-dollar client transformed by flipping go-to-market strategy (indirect to direct) through strategic alignment.
• Tangible impacts of relevancy: rapid customer acknowledgment and increased engagement.

Suggested Action Items

• Implement self-reflection for account managers to assess relevancy and customer insight levels.
• Build internal dialogues with executives (CFO, COO) to sharpen customer-centric approaches.
• Establish a dedicated insight strategist role to continually feed actionable insights to account leaders.

Closing Takeaways

• True differentiation in enterprise sales is now achieved through strategic relevance, deep customer insights, and advisory-level interactions.
• Account leaders must shift from product-centric to problem-centric strategies, continually validated by executive-level buyer engagement.

Guest:
Brian Shea

Principal, Lucrum Partners

brian@lucrumpartners.co

lucrumpartners.co

In this episode of Selling What’s Possible, host Dave Irwin and guest Dave Brock dive into why traditional, product-pushing sales methods no longer resonate with today’s buyers. They discuss how most customers complete the majority of their buying cycle on their own—and why sales teams must engage earlier by understanding and solving customer problems. Dave Brock explains how adopting a “business focused selling” mindset, including using customer focus and problem focus questionnaires, not only builds trust but also dramatically improves win rates, shortens buying cycles, and increases deal sizes. Real-world examples and actionable advice offer account executives a roadmap to transform from transactional sellers into strategic problem solvers.

Guest:
David Brock, Author “Sales Manager Survival Guide”, CEO at Partners in Excellence
https://www.linkedin.com/in/davebrock/
https://partnersinexcellenceblog.com/

Key takeaways:

Changing Buyer Behavior:

• Over 80% of buyers prefer a “rep-free” buying environment.
• Customers now navigate most of the buying process on their own.

Early Engagement & Pre-Intent:

• The importance of engaging before solution selection.
• Intercepting the buying process early to shape outcomes.

Business Focused Selling:

• Transitioning from a product-pitch mindset to a problem-solving approach.
• Building trust by understanding customer challenges and industry metrics.

Sales Transformation & Metrics:

• Doubling win rates, reducing “no decision” outcomes by 25%, and cutting buying cycles by 30–40%.
• Real-world examples demonstrating dramatic increases in average deal size.

Tools & Tactics:

• Using customer focus and problem focus questionnaires to build business acumen.
• Leveraging modern tools (e.g., AI like ChatGPT) to simulate customer conversations.

In this episode, Dave Irwin sits down with Keenan, author of Gap Selling, to explore why traditional sales approaches fail in enterprise account management. Keenan explains why buyers don’t act unless their current state is untenable and how account teams can drive change by focusing on diagnosing problems instead of pushing solutions. They discuss the psychology behind decision-making, the importance of business acumen, and how account teams can become trusted advisors. If you’re in sales or account management, this episode is packed with actionable insights to elevate your approach.

Guest: Keenan, CEO and Founder of A Sales Growth Company

Key takeaways:

1. People buy when the pain of staying the same is greater than the effort to change—salespeople must highlight this gap.
2. Enterprise account teams need to map decision-makers, including those who can say “no” but not “yes.”
3. Trust is built by deeply understanding the customer’s business, not just selling a product.
4. Many buyers don’t fully understand their own problems—great account executives help them figure it out.
5. Quarterly Business Reviews (QBRs) should focus on whether the customer is achieving business goals, not just product usage metrics.

In this episode, Craig Nelson and Dave Irwin explore how AI is transforming sales and account planning. The discussion focuses on foundational strategies, key use cases, and actionable insights for optimizing workflows and enabling enterprise growth.

Key takeaways:

• Start with Foundations: Establish clear governance and foundational use cases for AI adoption.
• Focus on High-Value Wins: Identify and implement a few impactful AI-enabled workflows to demonstrate success quickly.
• Break Silos: Integrate AI into cross-functional strategies to ensure company-wide benefits.
• Leverage AI for Hyper-Personalization: Utilize AI to align deeply with customer needs and enhance sales relevance.
• Treat AI as a Teammate: Incorporate AI thoughtfully to augment and accelerate workflows, not just as a standalone tool.
• Prepare for Long-Term Gains: Build a foundation now to capitalize on data-driven insights for strategic growth in the future.