Enablement Uncanned

AI, Email, and the Evolution of Marketing: How to stay in the inbox

In this episode of "Enablement Uncanned," Jack chats with David, CEO and co-founder of WithJoy.ai, a company reshaping real estate marketing with the power of AI. David shares insights from his journey as a tech entrepreneur, discussing how he leveraged AI for real estate insights and successfully acquired. Together, they dive into how AI is transforming marketing strategies in real estate, the challenges of email deliverability with tightening regulations, and the importance of using AI to offload tedious tasks while maintaining a personal, human touch. The conversation explores the concept of "AI amplification," where using AI effectively can make professionals more productive by handling repetitive work and allowing them to focus on higher-level tasks. David also shares how delivering hyper-personalized, value-driven email marketing helps teams stand out in an increasingly competitive landscape. Discover tips on improving email deliverability, avoiding AI "slop," and crafting authentic, uniquely personalized outreach in this insightful episode.

Tackling the AI Maturity Gap: Customer Support as a Growth Engine

In this episode of "Enablement Uncanned," Jack is joined by Rick DeLisi, a 20-year CX expert and researcher behind a groundbreaking industry study on AI maturity in customer service. Together, they delve into why high adoption rates of AI in customer support often fail to deliver full value, revealing how outdated practices and disjointed approaches hinder true transformation. Rick shares the surprising gap between widespread AI adoption and impactful results, while offering insights into how leading organizations are bridging this divide by turning contact centers into growth engines. He emphasizes that AI should not replace human interaction but enhance it, creating more meaningful connections and setting employees up for success. The conversation also explores how AI empowers frontline teams, simplifies processes, and helps executives unlock valuable insights from every customer interaction. Rick highlights the importance of balancing automation with human touch to improve not only customer satisfaction but also employee engagement. Tune in to learn how AI can elevate your customer experience strategy and make "help has arrived" a reality for both teams and customers.

How AI deep research agents enable smarter decision-making

In this episode of The Deep Dive, we tackle a challenge that every revenue and enablement professional knows all too well: the strategic intelligence bottleneck. How much time is your team losing to manual research, digging through endless documents, and piecing together insights from scattered sources? More importantly, what’s that time costing in terms of missed opportunities and delayed decisions? We explore how AI deep research agents are transforming this process, shifting the workflow from information gathering to strategic action. By automating the heavy lifting of research, these intelligent tools free up your team’s brightest minds to focus on what they do best—analyzing, strategizing, and driving results. From instantly generating market briefs to uncovering subtle competitive connections, we’ll unpack the game-changing potential of AI-powered insights. Tune in to learn how this technology can give your team back their time and level up decision-making across the board.

The enablement leader’s guide to a world-class kick-off

In this episode Jack talks with Sherridan Wills (Head of Enablement at Reputation) about the real purpose and power of sales kickoffs. They argue kickoffs are far more than parties — when designed strategically they’re the single most powerful tool for organizational alignment: communicating go-to-market strategy, rolling out new products, and unifying messaging across regions. Sherridan walks through how enablement’s role has matured from event-production to strategic orchestration — building a cross-functional team, defining clear learning objectives tied to business outcomes, and insisting every session be actionable (not just informative). They dig into practical planning: start with the “why", invest in high-impact learning (workshops, simulations) over spectacle, and hold presenters to practice and facilitation standards so sessions aren’t “death by PowerPoint.” Sherridan also highlights underrated details — cultural sensitivity, dietary/logistics, pre-work microlearning — that massively affect participant readiness and long-term impact.

The blueprint for revenue: top 6 tech drivers shaping enterprise

In this episode of Enablement Uncanned, we cut through the noise and break down the real forces shaping enterprise technology decisions in 2025. Drawing on insights from the newly released Voice of Customer Report 2025, we explore what’s truly driving investment in enablement platforms — and how buying committees are evolving to include not just sales and marketing, but also finance and IT. The data paints a clear picture of enablement’s transformation from a “nice-to-have” to a non-negotiable operational investment. From the surge in targeted AI adoption to the demand for measurable ROI and seamless integration, we unpack the top six tech drivers influencing vendor choices today — including consolidation, personalization, and the rise of channel enablement. With powerful real-world examples and hard ROI data, this episode offers a sharp, evidence-based look at how the enterprise tech landscape is shifting — and why enablement is now being treated as critical infrastructure for revenue growth.