Selling AI

More Is Not a Strategy: Selling AI in the Trust Economy Oct 14, 2026 00:51:45 In this conversation, Leslie Venetz shares her extensive sales experience and insights on the evolving landscape of sales, particularly in relation to AI and trust in the buyer-seller relationship. The discussion highlights the challenges sales professionals face in addressing buyer apprehensions about AI's impact on jobs and the importance of building trust amidst a rapidly changing market. The c

Your Buyer Doesn't Know What to Ask For Yet Sep 30, 2026 00:37:22 In this episode of Selling AI, Mike De Lonartis, the chief revenue officer at Verity, discusses the sales process around robotics and autonomous drones in warehouses. He shares insights on the challenges of the sales process, the evolution of the buyer's journey, and the demand creation cycle in the AI space. The conversation covers the role of the account executive (AE) in managing the sales proc

"You're Inspiring People to Mute Your Logo" — A RevOps Leader on AI Outbound. Sep 23, 2026 00:38:03 In this episode, Jimmy Downing, the VP of Revenue Operations at NextGlass, shares his journey into revenue operations, the impact of AI on go-to-market operations, and the evolving role of sales and marketing in the AI era. He also discusses the importance of soft skills in sales and the potential risks of rapid feature development in software tools.TakeawaysRevOps JourneyAI Impact on Go-to-Market

Build Your Campsite Where the Buyers Live Sep 3, 2026 00:31:26 Morgan J Ingram shares his journey from a sales development rep to a full sales cycle rep and trainer. He discusses the changing landscape of outbound sales and the importance of creativity and intention in connecting with buyers. The conversation also delves into the significance of in-person events and the role of pattern interruption in modern sales strategies. The conversation covers the impac

"Motivation Is the Gas Pedal. Logic Is Just the Steering Wheel." Aug 19, 2026 00:44:47 The conversation delves into the emotional psychology of buying, the transition from clinical psychology to sales, lessons from the corporate environment, and the role of emotional messaging in B2B sales. It explores the emotional journey in B2B sales and the significance of understanding emotional needs in decision-making. The conversation covers topics such as positioning products for the cuttin

The AI Committee Is Step Two Now, Not the Last Gate Aug 12, 2026 00:46:20 The conversation with Jean-Marc Chanoine covers his career arc, the evolution of Templafy, the impact of LLMs on document automation, the shift in software buying, and the engagement with AI strategy teams. It also delves into the importance of industry and process knowledge, the political aspect of buying, and the data play and IT-first discussion in the buying cycle. The conversation covers the

A New Approach to Sales Roleplay Jul 29, 2026 00:32:15 The conversation covers the introduction of Breakthrough AI, Neha Gupta's career journey, the evolution of role-playing, the importance of role-playing in sales, and the future of role-playing in sales. It delves into the impact of AI role-playing on communication skills in sales and the potential advancements in the role-playing space.TakeawaysAI role-playing for salesCommunication skills in sale

The Surprising Way Personality Types Can Boost Outreach Response Rates to 30% Jul 22, 2026 00:44:49 The conversation explores the use of AI in prospecting and client management, focusing on personality matching and psychological alignment. Gary Sinderbrand shares his journey in wealth management and the development of the Rainmaker app, which uses AI to identify psychological fit and improve prospecting outcomes. The discussion also delves into the potential of AI in client management and coachi

Holding Complexity Under Pressure: What Your Meeting Transcripts Actually Reveal Jul 16, 2026 00:37:09 The episode explores the application of AI in measuring leadership capacity through linguistic patterns. Logan Yonavjak, the co-founder and CEO of Readiness Engine, discusses the platform's AI-informed diagnostic capabilities and its impact on leadership readiness. The conversation delves into the use of AI in decision-making, team dynamics, and the future potential of generative AI.TakeawaysLeade

The Messaging Mistake Everyone Makes on LinkedIn (And How to Fix It in Two Sentences) Jul 8, 2026 00:33:24 The conversation delves into the evolution of outbound sales, the challenges of telemarketing and cold calling, common mistakes in LinkedIn outreach, effective messaging strategies, optimizing responses and follow-ups, and leveraging AI in sales outreach. The discussion highlights the transition from telemarketing to LinkedIn automation, the impact of COVID-19 on business models, and the rise of L

Go for No: The Counterintuitive Path to More Yeses Jul 1, 2026 00:46:44 In this episode of Selling AI, Andrea Waltz discusses the importance of handling rejection in sales and the methodology of 'Go for No.' She shares the origin story of the 'Go for No' strategy and its impact on sales. The conversation also delves into the key premises of the book and the strategies for disqualification in sales. Additionally, the discussion explores the mindset shift from wants to

AI Just Accelerates Your Inconsistency Jun 17, 2026 00:29:22 The conversation with Marvin Martinez delves into the changing landscape of prospecting and sales processes with the integration of AI and automation. Marvin's insights shed light on the importance of authenticity in automated messaging, the tactical implementation of AI in sales, and the future of AI and automation in the sales industry. Additionally, the discussion explores the operator's lens,

80% of the Deal Is Over Before the Buyer Talks to Sales Jun 3, 2026 00:39:42 In this episode, Warren Kucker and Braydan Young discuss the evolution of reference selling, the changing B2B buyer journey, and the role of AI in the sales process. Braden shares his journey as an entrepreneur and the founding of Slash Experts, a platform that revolutionizes the reference selling process. They explore the impact of references on the buyer's journey and the sales process, as well

AI Can Finally Kill CRM Data Entry. That Might Be the Problem. May 27, 2026 00:46:20 Eddie Reynolds, CEO of Union Square Consulting, shares insights on rev ops, CRM data entry, and leveraging AI in GoToMarket strategy. He discusses the impact of sales behavior, CRM implementation, and the role of AI in sales processes. The conversation delves into the challenges of deal qualification, stakeholder engagement, and the need for strategic sales approaches. The conversation covers the

Selling Into Domains Where You're Not the Expert, Yet May 20, 2026 00:27:37 Cash Monestine, an Enterprise Account Executive at AcuityMD, shares insights on selling complex data and AI software in the medtech industry. He discusses building credibility, leveraging AI in the sales process, and the evolving role of sales in specialized domains.TakeawaysSpecialized domain expertise is crucial for building credibility with buyers in the medtech industry.AI simplifies access to

AI Made Human Connection More Valuable, Not Less May 13, 2026 00:42:55 Zach Jones, co-founder and CEO of Waffle, discusses the unique approach of making AI the operator, not the assistant. He shares insights on building a sales approach, selling AI to non-technical businesses, and the line between automating business and staying close to customers. The conversation covers the challenges and opportunities in the tech space, the impact of personalized software solution

"We Had No Structure to Fully Structured" — Building Sales Process in Real Time May 6, 2026 00:40:02 Jim Robertiello, Director of B2B Sales at Poppin, shares his journey in sales and the evolution of Poppin from a startup to a nationally recognized brand. The conversation covers the early days of Poppin, the sales process, the pivot to office furniture, and the impact of COVID on the workplace and sales approach. The conversation covers topics related to sales, market expansion, and the impact of

"We've Had All This Data for 40 Years. The Actual Outcomes Have Not Changed." Apr 29, 2026 00:45:22 Jack Siney, co-founder and CRO at Front Race, discusses the challenges of implementing AI in sales, emphasizing the importance of the human element and the need for a middle layer in the sales process. He highlights the metric engine as a key lever for leveraging AI in the sales process and addresses the small sample size problem through behavior analysis. The conversation delves into the impact o

What Got You Here Won't Get You There — From Founder-Led Sales to Scale Apr 22, 2026 00:51:38 The conversation delves into the intersection of sales and AI, the early stage of sales, the transition to a fractional VP of sales, founder-led sales, building a sales team, and the characteristics of a great salesperson. The discussion also explores the importance of financial acumen and the involvement of founders in the sales process. The conversation delves into the characteristics and habits

"95% of Buying Decisions Are Emotional" — Why Your Sales Team Is Still Selling Logic Apr 15, 2026 00:39:20 The conversation delves into the importance of sales coaching, the impact of motivation and values on sales performance, the challenges of promoting salespeople to management roles, and the shift from being an expert to becoming a trusted advisor. It also explores the role of emotional decision-making in sales, the use of NLP in sales, and the fundamental meaning of sales as being of service to pe

Great Marketing Should Reduce Your Sales Calls Apr 1, 2026 00:32:34 The impact of AI on demand generation is explored in this conversation, with a focus on modern demand-gen philosophy, buyer research, and the shift from lead volume to pipeline velocity. The conversation also delves into the role of AI in content production, personalized follow-up, and the alignment of marketing and sales for revenue optimization.TakeawaysAI's role in demand generationShift from l

A Champion Isn't a Person — It's a Behavior That Shows Up When There's Good Friction Mar 26, 2026 00:42:51 In this episode, David Weiss challenges traditional sales methodologies and introduces the concept of deal management as a separate methodology. He redefines the role of a champion as a behavior rather than a person and discusses the process of identifying and developing champions. The conversation also explores the importance of understanding behavioral shifts throughout the sales cycle and the d

Buyer First Is a Behavior, Not a Statement — Carol Mahoney on What Most Companies Get Wrong Mar 18, 2026 00:35:16 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.TakeawaysBuyer-first approachAI coaching for salesRole

"AI Will Happily Solve the Wrong Problem Very Efficiently" Mar 11, 2026 00:48:48 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 mana

"No Decision" Is Not a Close-Loss Reason — Why Your CRM Data Is Lying to You Mar 4, 2026 00:41:54 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 conversa

The Standardization Problem That Shipping Said Was Impossible Got Solved in Two Years Feb 25, 2026 00:33:22 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.TakeawaysAI adoption in the maritime industryEvolution of sales roles and functionsChapters00:00 Introduction to Selling AI in Maritime07:15 Balancing Industry Ex

"If Your Dashboard Isn't Changing Behavior, What's the Point?" Feb 18, 2026 00:48:35 The conversation delves into the world of RevOps and Chantelle's experience, focusing on the challenges of scaling revenue without scaling headcount. It explores the role of dashboards, the evaluation of systems and tools at Asana, and the challenges of quota and revenue attainment in sales. The conversation delves into the challenges faced by RevOps teams in driving efficiency and productivity in

"We Are the Picks and Axes" — Selling the Infrastructure That Makes AI Actually Work Feb 11, 2026 00:40:55 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

The Tools Changed, The Job Didn't: An Enterprise AE's Take on AI in Sales Feb 4, 2026 00:37:57 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.TakeawaysSales Reps as ConductorsThe Evolution of Enterprise SalesThe Impact of AI o

How Enterprise Views Buying AI Products Jan 28, 2026 00:36:36 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

Building a Custom GPT for Every Rep on Your Team Jan 21, 2026 00:27:17 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.TakeawaysSales coaching with AIDifferentiating coa

"I Just Want to Play More Golf" — Why ROI Isn't Always the Right AI Pitch Jan 14, 2026 00:35:39 The conversation delves into the challenges and opportunities of selling AI in the legal industry, focusing on the evolution of time recording and email management in legal tech, the use of AI to solve time recording challenges, the sales process evolution and AI integration, skepticism and receptiveness to generative AI technology in the legal industry, privacy concerns and data access in AI time

Sales Enablement from Meeting Rooms to CustomGPTs Jan 8, 2026 00:35:25 The conversation delves into the evolution of sales enablement, the impact of AI on training processes, the use of AI for personalized onboarding, the synergy between sales enablement and rev ops, and the future of sales roles with AI. It highlights the shift towards revenue enablement, the transformation of enablement processes, the role of GPT in customized onboarding, the changing landscape of

The Kickoff Jan 4, 2026 00:02:11 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.

Episodes

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