Enablement Uncanned

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 role-play scenarios to sharpen skills before the big call. We unpack how this shift—from reactive reporting to proactive, step-by-step coaching—represents a fundamental change in how AI can empower sales teams.

Learn more about AI coaching tools and how they transform everyday selling by gauging buyer engagement in real time, surfacing exactly the right assets when needed, and building personalized digital sales rooms that keep deals moving. Just as importantly, it frees managers from repetitive follow-up so they can focus on high-impact coaching, while enabling sellers to spend more time on strategy, empathy, and relationship building. If you’ve ever wondered what separates a minimally viable AI tool from a true “most valuable player” in sales enablement, this conversation breaks it down.

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 reframing CRM training into a dating game to leaning on humor, storytelling, and cultural awareness, Mary challenges the tired trope that learning has to be boring. With insights on adult learning psychology, cultural sensitivity, and even weather-based engagement tactics, she breaks down how fun isn't frivolous—it's strategic.

The conversation goes deeper into the real-world challenges enablement professionals face, especially when proving value to skeptical leadership.

Whether it's leading with empathy, rethinking how we kick off training, or making people actually want the next session like it’s the next episode of their favorite show, this episode is packed with practical takeaways for anyone ready to break free from traditional, forgettable training. If you’ve ever wondered how to make enablement stick—and maybe even fun—this is your episode

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 listen. We break down the four essential types of workplace communication—verbal, non-verbal, written, and visual—and reveals how each plays a unique role in building trust, reducing conflict, and boosting productivity, especially across distributed teams and digital channels.

Takeaway practical strategies so you can transform your team’s communication habits, from keeping messages concise and authentic to leveraging AI tools for smarter collaboration and feedback.

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 activities. The discussion highlights industry data showing that while only a third of a sales rep’s time is spent actively selling, AI adoption is driving measurable revenue increases and helping teams overcome common challenges like content discovery and training retention.

The conversation doesn’t shy away from the complexities and potential pitfalls of AI in sales. The hosts examine both the advantages—such as improved coaching, real-time performance feedback, and smarter content management—and the drawbacks, including over-reliance on automation and the risk of losing the human touch. This is a nuanced conversation on how to leverage AI for smarter selling, what to watch out for as adoption accelerates, and actionable insights for integrating AI-driven solutions to boost sales effectiveness and team productivity.

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 emergence of intelligent sales assistants that automate routine tasks, the rapid advancement of AI-powered sales coaches offering real-time feedback and performance mentoring, and—most disruptively—the dawn of autonomous Agentic AI, capable of orchestrating complex, multi-step sales processes without human oversight.

The best way to understand these trends is of course by real-world examples, with that in mind, we highlight AI sales development reps that autonomously research prospects, personalize outreach, and schedule meetings. All this and a whole lot more on this episode of Enablement Uncanned!

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-building, and nuanced understanding of buyer needs. He points out that when sales teams over-rely on AI-generated content and automated outreach, they risk delivering generic experiences that fail to resonate with prospects, ultimately diminishing trust and engagement.

Tune in for a candid discussion on how enablement can reclaim its seat at the table and steer sales teams toward more meaningful, human-centered outcomes in an AI-saturated landscape.

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 stories, learning successful approaches real teams have made to keep sales, marketing, and dealers aligned and how they've put effort in ensuring consistent messaging and a unified customer experience throughout the go-to-market process.

By developing a strategic sales enablement plan that aligns with broader business goals, companies can ensure that both sales and marketing are moving in sync, ultimately accelerating revenue growth and improving customer satisfaction.

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 clear definition of enablement, exploring its core purpose: empowering teams with the knowledge, tools, and processes they need to succeed and adapt in an ever-changing landscape.

Looking ahead to 2025, the conversation highlights the expanding role of enablement professionals as they become key partners in business growth and transformation Whether you’re building an enablement function from scratch or optimizing an existing program, this episode has you covered with actionable insights.

And of course, the two discuss their "uncanned" takes on enablement, like "do you need sales experience to be a good enabler?".

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 streamlining workflows. The discussion highlights real-world challenges—like scattered content, time-consuming updates, and the need for personalized buyer experiences—and offers actionable strategies to overcome them.

Tune in to learn how leading organizations are consolidating their content, leveraging intelligent search, and enabling reps with self-serve customization features that keep messaging on-brand while boosting productivity. Whether you're looking to reduce wasted time, improve collaboration between sales and marketing, or gain deeper insights into content engagement, this episode delivers practical advice and proven solutions to help you elevate your sales enablement game. Don't miss out on these must-know tips for building a future-ready sales content process!

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 a powerful tool that can bridge the go-to-market gap and ignite growth. The two unpack how modern enablement empowers teams to move as one, equipping sellers with the right tools, insights, and confidence to crush their targets. From actionable frameworks to stories of transformation, this episode will help guide your team to successfully implement enablement.