The conversation delves into the buyer-first approach in sales, the role of AI coaching for sales teams, and the significance of mindset in sales success. Carole Mahoney shares insights on the importance of understanding the buyer's perspective, the development of AI coaching platforms for sales, and the impact of mindset on sales performance. Takeaways Buyer-first approach AI coaching for sales Role of mindset in sales Chapters 00:00 The Buyer-First Approach 10:58 AI Coaching for Sales 18:02 The Role of Mindset in Sales

The conversation delves into the power of storytelling in sales, emphasizing the importance of context, emotional response, and soft skills in the AI marketplace. It also explores the role of soft skills in business development and the relationship between process and context in sales. The conversation delves into the importance of context in AI processes, the transition from sales to project management, the shift from high-volume to high-touch sales approach, the impact of relationship building in business, handling objections and storytelling in sales, and the future of the sales process and buyer's journey. Takeaways Storytelling is a powerful tool in sales Soft skills are crucial in the AI marketplace Context is crucial Human touch in sales Chapters 00:00 The Power of Storytelling in Sales 05:25 The Impact of Soft Skills in Sales 11:28 The Significance of Soft Skills in AI Marketplace 19:25 The Role of Soft Skills in Sales and Business Development 26:08 The Role of Context in AI Processes 31:10 The Impact of Relationship Building in Business and Sales 37:39 Structuring Sales Calls and Handling Objections 45:05 The Future of Sales Process and Buyer's Journey

The conversation delves into the evolution of RevOps, the underutilization of conversational intelligence in RevOps, and the access to conversations in sales and marketing. It explores the shift from traditional CRM data tooling to driving real buyer signals, the importance of targeted outreach, and the potential of conversational intelligence to replace the need for CRM data filling. The conversation delves into the rethinking of CRM and conversation stages, understanding close loss reasons, the importance of signals and contextual insights, effective signal identification and utilization, building effective signal processes, adoption and usage of sales systems and processes, and the future of AI and automation in sales operations. Key takeaways include the role of AI and automation in sales operations and the emphasis on context and value in sales processes. Takeaways RevOps evolution Conversational intelligence Data-driven insights AI and automation in sales operations The importance of context and value in sales processes Chapters 00:00 The Evolution of RevOps 13:07 Access to Conversations in Sales and Marketing 22:21 Rethinking CRM and Conversation Stages 27:38 Effective Signal Identification and Utilization 33:24 Adoption and Usage of Sales Systems and Processes

The conversation delves into the challenges and opportunities of selling AI technology in the maritime industry. It explores the evolution of sales roles, the impact of AI on the industry, and the future of AI adoption in sales processes. Takeaways AI adoption in the maritime industry Evolution of sales roles and functions Chapters 00:00 Introduction to Selling AI in Maritime 07:15 Balancing Industry Expertise and Sales Role 12:59 Innovative AI Applications in Maritime 19:30 AI Adoption and Sales Process 30:22 Future of Sales Roles and AI Adoption

The conversation delves into the world of Revenue Operations (RevOps) and Chantelle's experience in the space. It covers her transition to Asana Benefits, the role of RevOps, the importance of dashboards and data analysis, scaling revenue without growing headcount, the future of RevOps, and the challenges of revenue attainment and quota targets. The conversation delves into the challenges faced by RevOps teams in driving efficiency, managing tension between sales and marketing, and the evolving role of RevOps in the future. It also explores the potential impact of GTM engineers on RevOps teams. Takeaways RevOps as a Strategic Function Challenges of RevOps Leadership RevOps teams face challenges in driving efficiency and managing tension between sales and marketing. The evolution of RevOps and the role of GTM engineers in the future. Chapters 00:00 Introduction to RevOps and Chantelle's Background 06:34 Scaling Revenue Without Growing Headcount 17:20 Future of RevOps and Revenue Efficiency 25:26 Challenges of Revenue Attainment and Quota Targets 30:26 The Tension Between Sales and Marketing 45:27 The Role of RevOps in the Future

The conversation delves into the evolution of enterprise sales, the journey within Alteryx, the impact of AI on sales objections, challenges in selling AI, and the use of AI tools in sales leadership. It explores the changing landscape of enterprise sales, the role of AI in reshaping sales processes, and the challenges faced in selling AI solutions. Additionally, it highlights the use of AI tools in sales leadership and the complexities of implementing AI in sales strategies. The conversation covers the topics of building internal processes and GPTs, the buy vs. build scenario and sales conversation, changing buying behavior and approval process, competition and sales process challenges, and the impact of AI on job roles. Takeaways Sales Evolution AI in Enterprise Sales Buy vs. build scenario Changing buying behavior Impact of AI on job roles Chapters 00:00 Evolution of Enterprise Sales 06:01 Positioning and Sales Process 11:32 Challenges in Selling AI 17:55 AI Tools in Sales Leadership 24:27 Buy vs. Build Scenario and Sales Conversation 31:31 Competition and Sales Process Challenges

The conversation delves into the evolution of enterprise sales, the impact of AI on sales techniques, and the role of AI in the maritime industry. It explores the changing buyer behavior and the future of AI in sales, highlighting the role of sales reps as conductors in solving complex problems and driving revenue. Takeaways Sales Reps as Conductors The Evolution of Enterprise Sales The Impact of AI on Sales The Role of AI in Maritime Industry Chapters 00:00 Introduction to Enterprise Sales Evolution 06:32 Evolution of Sales Techniques 19:44 Buyer Behavior and AI in Maritime Industry 30:52 The Future of AI in Sales

The conversation delves into the challenges of managing multiple stakeholders in enterprise sales, with a focus on the transition from a restaurant franchise to a sales career. It explores the lessons learned from the restaurant business and ad sales, comparing ad tech sales with SaaS sales. The discussion also covers the sales process and challenges in selling True Rating, including the ROI pitch and objections. Additionally, it highlights the data-driven play and the approach to handling objections in the sales process. The conversation covers the importance of balancing storytelling and data in sales pitches, as well as the challenges and strategies for stakeholder management and alignment in complex deals. Takeaways Managing multiple stakeholders in enterprise sales Transition from restaurant franchise to sales career Storytelling vs. Data Stakeholder Management Chapters 00:00 Introduction to Managing Multiple Stakeholders in Enterprise Sales 05:43 Comparison of Ad Tech Sales and SaaS Sales 13:39 ROI Pitch and Objections in Sales Process 18:50 Data-Driven Play and Handling Objections

The conversation delves into the innovative use of AI in sales coaching, highlighting the challenges, benefits, and tactical approaches. It explores the impact of AI on sales coaching and the potential pitfalls to avoid. The role of AI in exposing coaching practices is also discussed, providing valuable insights for sales leaders and professionals. Takeaways Sales coaching with AI Differentiating coaching, training, and feedback Chapters 00:00 Transition into Sales and Coaching 06:36 Custom GPT for Sales Coaching 15:05 Impact of AI on Sales Coaching 23:41 Mistakes to Avoid in Implementing AI in Sales Coaching

"I Just Want to Play More Golf" — Why ROI Isn't Always the Right AI Pitch What happens when you pitch a lawyer on billing 30% more hours and they say they'd rather leave early to hit the golf course? You learn that ROI isn't always the story that closes deals. James Lawler is the Managing Director of TriCoStar, an AI-powered time recording and email management platform built specifically for law firms. His company has been in legal tech for 38 years—his dad started it in the late 80s with a device called a Psion that most of us have never heard of. Today, James is doing founder-led sales into one of the most change-resistant industries out there. In this episode, we dig into what it actually takes to sell AI to buyers who are skeptical by profession. Turns out, the biggest objection isn't whether AI works—it's whether it'll catch them checking football scores. We cover: → Why privacy concerns beat performance skepticism in conservative industries → How James uses Copilot live during sales calls to translate technical answers into plain language → The difference between selling "bill more hours" vs. "get your evenings back"—same product, completely different pitch → What happens to the legal profession if firms automate paralegal work (and why apprenticeship-style contracts might make a comeback) → How to keep deals warm without filling inboxes with boilerplate when you're running founder-led sales If you're selling into traditional industries or trying to figure out how AI fits into your own sales motion, this one's worth your time. 🎧 Follow Selling AI on Apple Podcasts, Spotify, and YouTube.

Molly Sestak has spent years building sales enablement programs from scratch—and now she's using AI to do in 5 minutes what used to take hours. In this episode, we dig into how custom GPTs can create truly personalized onboarding plans for new reps (not just role-specific templates), and why the combination of RevOps and Enablement is becoming a powerhouse pairing. Molly shares her vision for the future of sales teams: leaner on the selling side, more robust on the operational side, with reps acting as conductors orchestrating AI-powered workflows. If you're in enablement trying to figure out where to start with AI, this one's for you.

The Selling AI Podcast focuses on generating revenue with AI tools and simplifying decisions for buyers, as well as adapting sales strategies to navigate the AI shift in real time.