Enablement Uncanned

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.

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they delve into why high adoption rates of AI in customer support often fail to deliver full value, revealing how outdated practices and disjointed approaches hinder true transformation.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.

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.

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.

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.

Sales enablement is no longer just a support function—it’s the backbone of growth. In this episode of Enablement Uncanned, we cut through the noise with hard data that reveals how the industry has matured heading into 2025. From a 49% higher win rate for companies with defined enablement strategies to onboarding speeds that slash ramp times nearly in half, the numbers prove enablement is now table stakes for any competitive sales organization.

We also unpack how shifting buyer behavior—where up to 90% of the journey is complete before a rep even enters the conversation—is redefining what sales teams need to deliver in those high-stakes final moments.

But that’s just the start. We dive into the trillion-dollar cost of sales and marketing misalignment, the underuse of content that drains millions in missed opportunities, and why coaching, training, and AI-powered tools are becoming critical levers for performance. You’ll hear how leadership is tying enablement directly to revenue growth, what the data says about customer expectations, and why enablement is fast becoming the central nervous system of the entire revenue engine.

In this episode of Enablement Uncanned, we pull back the curtain on a side of sales that often gets overlooked: security, compliance, and trust. Joined by Chris Sershon, Acting Director of Governance, Risk, and Compliance at Bigtincan, we explore why security has become a top buying criterion, how deals stall when compliance is left too late, and why trust is now as much a selling point as ROI. From third-party vendor risks to the rising complexity of AI security, Chris shares hard-hitting insights from more than a decade in cybersecurity.

We also dive into the practical side: how enablement and sales teams can get ahead of compliance questions, turn certifications into selling points, and build confidence with buyers before IT ever enters the room. If you’ve ever lost a deal at the eleventh hour because of security red flags—or want to make sure you never do—this conversation will change the way you think about enablement, trust, and the future of selling.

Drowning in dashboards? Tired of waiting weeks for data you needed yesterday? In this episode of Enablement Uncanned: AI Talk, we unpack how AI is completely changing the game for enablement and go-to-market teams. Instead of relying on analysts or wrestling with pivot tables, imagine being able to ask your business data a plain-English question—and get instant, actionable answers. From proving impact to the C-suite, to uncovering which content actually drives closed-won deals, this new class of enablement analytics AI is taking teams from buried in noise to laser-focused insights.

We explore how these tools go beyond surface-level reporting, bridging the gap between correlation and causation, and giving leaders confidence in the “why” behind their results. You’ll hear how AI helps pinpoint winning content, decode buyer engagement patterns, and tie training programs directly to revenue impact—all without needing a PhD in dashboards. If you’ve ever wondered how to turn your mountain of data into a true competitive advantage, this conversation is your guide to shifting from data burden to data ally.

AI has flooded the sales enablement world—but not all tools deliver on the hype. In this episode of Enablement Uncanned: AI Talk, we cut through the noise to separate the “minimally viable products” from the true “most valuable players.” We explore how to spot the difference between flashy demos that fizzle out and solutions that actually transform how teams work.

You’ll hear about the green flags that signal real impact—contextual intelligence, embedded workflows, automation that saves hours, and trustworthy data—and the red flags that should make you think twice. We break down the practical questions to ask, the pitfalls to avoid, and the game-changing benefits when you get it right. Whether you’re evaluating AI for onboarding, coaching, or content delivery, this episode gives you the framework to tell hype from value and make smarter choices for your team.

In this episode, Jack Naish sits down with two of his own teammates, Hadden Smith and Hari Keogh, to dig into what life is really like as an SDR. From the grind of daily outreach to the most optimal workflow, they share what actually works, what doesn’t, and how they’ve learned to find their rhythm in a role that demands persistence above all else.

We also get into bigger questions—like whether great sellers are born or made—and the small details that make a big difference, like keeping your CRM tight and tailoring outreach so it feels human. It’s an honest look at sales development from the people living it every day, with plenty of practical insights you can take back to your own sales process.