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 ch...

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they delve into why high adoption rates of AI in customer support often fail to deliver full value, revealing how outdated practices and disjointed approaches hinder true transformation.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

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...

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 thr...

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 an...

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...

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. Fr...

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 im...

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...

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 gr...

In this episode we explore the rise of AI coaching in sales and spotlight Bigtincan’s Genie Assistant—a next-generation tool designed to go far beyond dashboards and data. While most AI platforms simply report what’s happening in your pipeline, Genie acts like a true sales coach: anticipating objections, suggesting precise talk tracks, creating custom buyer content on the fly, and even running rol...

In this episode of Enablement Uncanned, Jack Naish sits down with Mary Dildy, a passionate sales enablement leader, to explore the concept of “edutainment”—where education meets entertainment in the world of enablement. Mary shares her journey from frontline sales to her evolving role in revenue enablement, offering bold and refreshing takes on how learning should be experienced, not endured. From...

The staggering reality of workplace communication is this: workers spend nearly their entire workweek on communicating—often with little to show for it. In this episode, we dive into the do's and the don'ts on communication. Simply increasing the volume of messages isn’t the answer. Instead, it’s about mastering the art of effective communication: knowing what to say, how to say it, and when to li...

In this episode of 'AI in Sales: The Good, The Bad, and The Ugly,' Jack Naish is joined by Mike Pritchett to dive into the transformative impact of artificial intelligence on modern sales organizations. They explore how AI-powered tools are reshaping sales workflows by automating repetitive tasks, prioritizing leads, and personalizing outreach—freeing up reps to focus on high-value selling activit...

In this episode of Enablement Uncanned, we dive into the shift happening right now in sales enablement, driven by the rise of Agentic AI. Drawing on insights from the brand-new in the 2025 Aragon Research Globe™ for Sales Enablement Platforms report, we unpack how sales enablement platforms are evolving far beyond traditional content management. We dissect three transformative trends: the emergenc...

In this episode of "Enablement Uncanned," Dave Sweeney dives into the provocative claim that AI is undermining the sales profession, challenging the widespread belief that more automation always leads to better results. Sweeney explores how AI-driven tools, while promising efficiency, often risk eroding the human elements critical to successful selling—like authentic communication, relationship-bu...

In this episode, we take a deep dive through the essential strategies for bridging the gap between sales and marketing teams to drive impactful business outcomes. The discussion highlights the importance of fostering a culture of collaboration, where cross-functional teams leverage shared tools and transparent communication to break down silos. We go over real-world examples of alignment success s...

In this episode of Enablement Uncanned we are joined by Viktorija Hartwell, Professional Enablement Consultant, to break down what enablement truly means in today’s fast-paced business environment. Jack and Viktorija discuss how enablement has evolved from simple training and onboarding to a strategic function that drives measurable outcomes across organizations of all sizes. The two define a clea...

In this episode of Enablement Uncanned, we dive into the essentials of sales content creation and management, exploring how modern enablement platforms are transforming the way sales teams access, personalize, and share content. Discover why so many reps struggle to find the right assets, how marketing can finally track content effectiveness, and the critical role of AI-powered tools in streamlini...

Sales, marketing, and product often march to different beats, leaving revenue on the table and buyers in the dark. Today, our host Jack Naish is joined by Ben Pearce, Strategic Growth Director, to detail how teams can challenge the status quo and approach enablement successfully by tackling misaligned messaging, siloed teams, and outdated enablement tactics. Enablement isn’t just a buzzword, it’s...

Ready to transform your sales process from ordinary to unforgettable? In this episode, we break down the most impactful sales touchpoints that move buyers from curious to committed—without the clichés. Discover how to create engaging, value-driven experiences at every stage of the journey, from that first cold call to the final handshake (or e-signature). We’ll unpack: The art of the first impress...

In this episode of Enablement Uncanned, Jack Naish is joined with Lisa Borg, SVP of Marketing at Acumen, who shares her perspective on the evolving role of marketing in driving business growth and customer engagement with a focus on the transformative impact of AI and its various tools and capabilities. Lisa has formed a strong perspective on AI and how teams are using it on a day-to-day basis and...

In this episode, we explore the transformation happening within the enablement world, where we are seeing a shift from traditional sales enablement to holistic revenue enablement. We discuss why enabling all customer-facing roles—not just sellers—is essential for delivering seamless buying experiences and driving growth. The discussion highlights how breaking down silos and aligning teams around s...

Does one size fit all in enablement? In this episode of Enablement Uncanned, Jack Naish sits down with Hadia Madni, a leader in commercial excellence, to explore the evolving landscape of sales enablement in complex organizations. Hadia shares her journey implementing enablement technology, the lessons learned from driving adoption, and why workflow-driven solutions are key to lasting impact. Hadi...

Have you ever wondered where your Generative AI answers are actually coming from? How can you know if it's to be trusted, and how can you fine tune the results to fit your needs? In this episode of Enablement Uncanned, Mark and Sarah dig deep into the different types of data sources and knowledge scopes that generative AI can utilize, such as: company content, analytics, general language models, a...