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FAQs about Selling AI:How many episodes does Selling AI have?The podcast currently has 20 episodes available.
May 20, 2026Selling Into Domains Where You're Not the Expert, YetCash 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 data and aids in change management, making it easier to close deals.Sales is evolving to require exceptional knowledge and expertise in the industry, emphasizing the importance of becoming a subject matter expert.Chapters00:00 The Future of Sales and Industry Expertise...more28minPlay
May 13, 2026AI Made Human Connection More Valuable, Not LessZach 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 solutions on small businesses, and the future of work in a world with AI and automation.TakeawaysAI as the operator, not the assistantHuman connection becomes more valuable in the AI era Personalized software solutions for small businessesThe future of work in a world with AI and automationChapters00:00 Introduction to Waffle and AI Approach05:16 Transitioning to an AI-Driven World13:43 Leveraging AI for Automation and Human Interaction22:53 Challenges and Opportunities in the Tech Space30:03 The Future of Work in a World with AI and Automation...more43minPlay
May 06, 2026"We Had No Structure to Fully Structured" — Building Sales Process in Real TimeJim 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 AI on the furniture industry. It also delves into the evolving trends in office space utilization and the shift towards hybrid work models.TakeawaysPersona-Driven SellingChannel Complexity Sales ProcessMarket ExpansionAI in Furniture IndustryTrends in Office Space UtilizationChapters00:00 The Journey to Poppin06:30 Pivot to Office Furniture13:09 Challenges with Big Clients20:18 Sales Process and Client Engagement28:09 AI and Trends in Office Space35:43 Future Trends and Work Models...more41minPlay
April 29, 2026"We've Had All This Data for 40 Years. The Actual Outcomes Have Not Changed."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 of AI and data on sales motions, challenges post-COVID, unique success variables, data-driven insights, behavioral analysis with AI, AI and data utilization, AI solutions and sea change, AI noise and automation, future of go-to-market, the great upheaval, efficiency in sales and marketing, buyer's journey and automation, and AI adoption and implementation. The discussion highlights the importance of company-specific data, challenges of AI noise in the market, and the impact of AI on workforce and market dynamics.TakeawaysImportance of the human element in AI implementationLeveraging the metric engine for AI in sales AI's impact on sales motions and data insightsChallenges and opportunities in AI adoption and implementationChapters00:00 Introduction to Jack Siney and Front Race05:10 The Human Element in AI Implementation15:32 The Metric Engine and Leveraging AI in Sales26:02 Sales Motions and Data Insights31:13 AI and Data Utilization36:41 Future of Go-to-Market42:06 Efficiency in Sales and Marketing...more46minPlay
April 22, 2026What Got You Here Won't Get You There — From Founder-Led Sales to ScaleThe 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 of top 10% sales reps, the challenges of selling in the current market, considerations for career progression and company selection, and the changing buyer's journey in the sales process.TakeawaysSales Reps and AIEarly Stage SalesFounder-Led SalesFinancial AcumenScaling Sales Teams Top 10% sales reps have a different approach to their work and lifeThe buyer's journey has changed, and sales reps need to adapt to itChapters00:00 Introduction to Sales and AI10:07 Founder-Led Sales and Growth Journey18:08 Building a Sales Team and Founder Involvement26:27 Characteristics of a Great Salesperson39:57 Career Progression and Company Selection44:57 The Changing Buyer's Journey...more52minPlay
April 15, 2026"95% of Buying Decisions Are Emotional" — Why Your Sales Team Is Still Selling LogicThe 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 people.TakeawaysSales coaching is about understanding the drivers behind why a person wants to work in a role and aligning their motivations with their career plan.Sales managers often only make time to work with individuals when the individual is not performing, leading to a fundamental problem in sales management.The fundamental meaning of sales is to be of service to people, and to be of service, you have to listen to find out what the problem is and then provide the right kind of solution.Chapters00:00 The Role of Sales Coaching11:52 Emotional Decision Making in Sales26:52 Becoming a Trusted Advisor36:08 Neuro-Linguistic Programming (NLP) in Sales...more40minPlay
April 01, 2026Great Marketing Should Reduce Your Sales CallsThe 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 lead volume to pipeline velocityChapters00:00 The Modern Demand-Gen Philosophy10:12 The Impact of AI on Demand Generation29:46 Operational Efficiency with AI...more33minPlay
March 26, 2026A Champion Isn't a Person — It's a Behavior That Shows Up When There's Good FrictionIn 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 distinction between deal management and sales methodologies. The conversation delves into the challenges of sales tools, the need to rethink sales behavior and metrics, the concept of a system of action, the ineffective leadership structure, the importance of leadership enablement, the role of sales enablement and leadership training, the role of neuroscience in sales, and the future of the sales process and buyer's journey.TakeawaysChampion is a behaviorSeparating functional roles from behavioral signalsDeal management as a separate methodology from sales methodologies Sales enablement should focus on leader enablementTriggering the amygdala is crucial in driving urgency in salesThe role of the salesperson is sense-making and providing deep domain expertise to buyersChapters00:00 Redefining Deal Management07:06 Identifying and Developing Champions14:23 Behavioral Shifts Throughout the Sales Cycle21:10 The Purpose of Sales Methodologies and Tech27:45 Ineffective Leadership Structure34:50 Neuroscience in Sales and Triggering the Amygdala...more43minPlay
March 18, 2026Buyer First Is a Behavior, Not a Statement — Carol Mahoney on What Most Companies Get WrongThe 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 of mindset in salesChapters00:00 The Buyer-First Approach10:58 AI Coaching for Sales18:02 The Role of Mindset in Sales...more36minPlay
March 11, 2026"AI Will Happily Solve the Wrong Problem Very Efficiently"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.TakeawaysStorytelling is a powerful tool in salesSoft skills are crucial in the AI marketplace Context is crucialHuman touch in salesChapters00:00 The Power of Storytelling in Sales05:25 The Impact of Soft Skills in Sales11:28 The Significance of Soft Skills in AI Marketplace19:25 The Role of Soft Skills in Sales and Business Development26:08 The Role of Context in AI Processes31:10 The Impact of Relationship Building in Business and Sales37:39 Structuring Sales Calls and Handling Objections45:05 The Future of Sales Process and Buyer's Journey...more49minPlay
FAQs about Selling AI:How many episodes does Selling AI have?The podcast currently has 20 episodes available.