<![CDATA[Selling AI]]>Sellers learning from sellers how to navigate the new world of selling AI, with AI.

]]>https://gettopiq.ai/selling-ai-podcastRiverside.fm (https://riverside.com)Sun, 31 May 2026 14:52:45 GMTSun, 04 Jan 2026 18:56:50 GMT60Warren Kucker<p>Sellers learning from sellers how to navigate the new world of selling AI, with AI.</p>episodicWarren Kuckerwarren@basiq.workno<![CDATA[AI Can Finally Kill CRM Data Entry. That Might Be the Problem.]]>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 challenges of sales pipeline management, the impact of AI on sales processes, and the evolving role of CROs in tech-driven sales organizations. It also delves into the importance of customer journey mapping and the need for foundational definitions and processes in go-to-market strategy and operations.

Takeaways

  • Rev ops and AI
  • Sales behavior impact
  • CRM implementation challenges Sales pipeline management requires clear qualification criteria and visibility into the sales process.
  • AI tools can automate data entry, provide coaching, and improve deal management for sales reps.
  • Customer journey mapping and foundational definitions are essential for effective go-to-market strategy and operations.

Chapters

  • 00:00 Rev Ops and AI in GoToMarket Strategy
  • 09:40 Deal Qualification and Strategic Sales Approaches
  • 23:28 Sales Pipeline Management Challenges
  • 29:20 Impact of AI on Sales Processes
  • 36:37 Analytical Approach to Sales Process

    GTM Science Podcast: Spotify: Here & Apple: Here
    GTM Efficiency Pyramid Framework: Here

    GTM  Metrics Framework: Here
    GTM Science Newsletter: Here

    Eddie Reynolds' LinkedIn: Here

]]>4625fc24-3d8b-4047-a747-41f0a9a9d4d3Wed, 27 May 2026 14:00:00 GMT<p>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 challenges of sales pipeline management, the impact of AI on sales processes, and the evolving role of CROs in tech-driven sales organizations. It also delves into the importance of customer journey mapping and the need for foundational definitions and processes in go-to-market strategy and operations.</p><p></p><p>Takeaways</p><ul><li>Rev ops and AI</li><li>Sales behavior impact</li><li>CRM implementation challenges Sales pipeline management requires clear qualification criteria and visibility into the sales process.</li><li>AI tools can automate data entry, provide coaching, and improve deal management for sales reps.</li><li>Customer journey mapping and foundational definitions are essential for effective go-to-market strategy and operations.</li></ul><p></p><p>Chapters</p><ul><li>00:00 Rev Ops and AI in GoToMarket Strategy</li><li>09:40 Deal Qualification and Strategic Sales Approaches</li><li>23:28 Sales Pipeline Management Challenges</li><li>29:20 Impact of AI on Sales Processes</li><li>36:37 Analytical Approach to Sales Process<br /><br />GTM Science Podcast: Spotify: <a rel="noopener noreferrer nofollow" href="https://open.spotify.com/show/1CM3rmelcdtm6gJVL0PtMK?si=0d48f630ae844884" target="_blank">Here</a> &amp; Apple: <a rel="noopener noreferrer nofollow" href="https://podcasts.apple.com/us/podcast/revops-corner/id1619571311" target="_blank">Here</a><br />GTM Efficiency Pyramid Framework: <a rel="noopener noreferrer nofollow" href="https://unionsquareconsulting.com/frameworks/the-gtm-efficiency-pyramid-framework/" target="_blank">Here</a><p>GTM  Metrics Framework: <a rel="noopener noreferrer nofollow" href="https://unionsquareconsulting.com/frameworks/the-gtm-metrics-index/" target="_blank">Here</a><br />GTM Science Newsletter: <a rel="noopener noreferrer nofollow" href="https://unionsquareconsulting.com/newsletter/" target="_blank">Here</a><br /></p><p>Eddie Reynolds' LinkedIn: <a rel="noopener noreferrer nofollow" href="https://www.linkedin.com/in/edwardreynolds" target="_blank">Here</a><br /><br /></p></li></ul>no00:46:20121AI Can Finally Kill CRM Data Entry. That Might Be the Problem.full<![CDATA[Selling Into Domains Where You're Not the Expert, Yet]]>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.

Takeaways

  • Specialized 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.

Chapters

  • 00:00 The Future of Sales and Industry Expertise
]]>406c82be-1196-4bb9-9a5f-9f76610c1079Wed, 20 May 2026 14:00:00 GMT<p>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.</p><p></p><p>Takeaways</p><ul><li>Specialized domain expertise is crucial for building credibility with buyers in the medtech industry.</li><li>AI simplifies access to data and aids in change management, making it easier to close deals.</li><li>Sales is evolving to require exceptional knowledge and expertise in the industry, emphasizing the importance of becoming a subject matter expert.</li></ul><p></p><p>Chapters</p><ul><li>00:00 The Future of Sales and Industry Expertise</li></ul>no00:27:37120Selling Into Domains Where You're Not the Expert, Yetfull<![CDATA[AI Made Human Connection More Valuable, Not Less]]>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 solutions on small businesses, and the future of work in a world with AI and automation.

Takeaways

  • AI as the operator, not the assistant
  • Human connection becomes more valuable in the AI era Personalized software solutions for small businesses
  • The future of work in a world with AI and automation

Chapters

  • 00:00 Introduction to Waffle and AI Approach
  • 05:16 Transitioning to an AI-Driven World
  • 13:43 Leveraging AI for Automation and Human Interaction
  • 22:53 Challenges and Opportunities in the Tech Space
  • 30:03 The Future of Work in a World with AI and Automation
]]>5c45bc93-bf15-4974-ba78-6ddb11d309dcWed, 13 May 2026 14:00:00 GMT<p>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 solutions on small businesses, and the future of work in a world with AI and automation.</p><p></p><p>Takeaways</p><ul><li>AI as the operator, not the assistant</li><li>Human connection becomes more valuable in the AI era Personalized software solutions for small businesses</li><li>The future of work in a world with AI and automation</li></ul><p></p><p>Chapters</p><ul><li>00:00 Introduction to Waffle and AI Approach</li><li>05:16 Transitioning to an AI-Driven World</li><li>13:43 Leveraging AI for Automation and Human Interaction</li><li>22:53 Challenges and Opportunities in the Tech Space</li><li>30:03 The Future of Work in a World with AI and Automation</li></ul>no00:42:55119AI Made Human Connection More Valuable, Not Lessfull<![CDATA["We Had No Structure to Fully Structured" — Building Sales Process in Real Time]]>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 AI on the furniture industry. It also delves into the evolving trends in office space utilization and the shift towards hybrid work models.

Takeaways

  • Persona-Driven Selling
  • Channel Complexity Sales Process
  • Market Expansion
  • AI in Furniture Industry
  • Trends in Office Space Utilization

Chapters

  • 00:00 The Journey to Poppin
  • 06:30 Pivot to Office Furniture
  • 13:09 Challenges with Big Clients
  • 20:18 Sales Process and Client Engagement
  • 28:09 AI and Trends in Office Space
  • 35:43 Future Trends and Work Models
]]>2e9b94a0-e0ea-4419-9a26-54e9240af359Wed, 06 May 2026 14:00:00 GMT<p>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 AI on the furniture industry. It also delves into the evolving trends in office space utilization and the shift towards hybrid work models.</p><p></p><p>Takeaways</p><ul><li>Persona-Driven Selling</li><li>Channel Complexity Sales Process</li><li>Market Expansion</li><li>AI in Furniture Industry</li><li>Trends in Office Space Utilization</li></ul><p></p><p>Chapters</p><ul><li>00:00 The Journey to Poppin</li><li>06:30 Pivot to Office Furniture</li><li>13:09 Challenges with Big Clients</li><li>20:18 Sales Process and Client Engagement</li><li>28:09 AI and Trends in Office Space</li><li>35:43 Future Trends and Work Models</li></ul>no00:40:02118"We Had No Structure to Fully Structured" — Building Sales Process in Real Timefull<![CDATA["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.

Takeaways

  • Importance of the human element in AI implementation
  • Leveraging the metric engine for AI in sales AI's impact on sales motions and data insights
  • Challenges and opportunities in AI adoption and implementation

Chapters

  • 00:00 Introduction to Jack Siney and Front Race
  • 05:10 The Human Element in AI Implementation
  • 15:32 The Metric Engine and Leveraging AI in Sales
  • 26:02 Sales Motions and Data Insights
  • 31:13 AI and Data Utilization
  • 36:41 Future of Go-to-Market
  • 42:06 Efficiency in Sales and Marketing
]]>ae6c7d5b-1355-4dbd-9fda-5c9b9e657ee7Wed, 29 Apr 2026 14:00:00 GMT<p>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.</p><p></p><p>Takeaways</p><ul><li>Importance of the human element in AI implementation</li><li>Leveraging the metric engine for AI in sales AI's impact on sales motions and data insights</li><li>Challenges and opportunities in AI adoption and implementation</li></ul><p></p><p>Chapters</p><ul><li>00:00 Introduction to Jack Siney and Front Race</li><li>05:10 The Human Element in AI Implementation</li><li>15:32 The Metric Engine and Leveraging AI in Sales</li><li>26:02 Sales Motions and Data Insights</li><li>31:13 AI and Data Utilization</li><li>36:41 Future of Go-to-Market</li><li>42:06 Efficiency in Sales and Marketing</li></ul>no00:45:22117"We've Had All This Data for 40 Years. The Actual Outcomes Have Not Changed."full<![CDATA[What Got You Here Won't Get You There — From Founder-Led Sales to Scale]]>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 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.

Takeaways

  • Sales Reps and AI
  • Early Stage Sales
  • Founder-Led Sales
  • Financial Acumen
  • Scaling Sales Teams Top 10% sales reps have a different approach to their work and life
  • The buyer's journey has changed, and sales reps need to adapt to it

Chapters

  • 00:00 Introduction to Sales and AI
  • 10:07 Founder-Led Sales and Growth Journey
  • 18:08 Building a Sales Team and Founder Involvement
  • 26:27 Characteristics of a Great Salesperson
  • 39:57 Career Progression and Company Selection
  • 44:57 The Changing Buyer's Journey
]]>39697699-a74d-46c8-b0dc-2117512a86adWed, 22 Apr 2026 14:00:00 GMT<p>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 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.</p><p></p><p>Takeaways</p><ul><li>Sales Reps and AI</li><li>Early Stage Sales</li><li>Founder-Led Sales</li><li>Financial Acumen</li><li>Scaling Sales Teams Top 10% sales reps have a different approach to their work and life</li><li>The buyer's journey has changed, and sales reps need to adapt to it</li></ul><p></p><p>Chapters</p><ul><li>00:00 Introduction to Sales and AI</li><li>10:07 Founder-Led Sales and Growth Journey</li><li>18:08 Building a Sales Team and Founder Involvement</li><li>26:27 Characteristics of a Great Salesperson</li><li>39:57 Career Progression and Company Selection</li><li>44:57 The Changing Buyer's Journey</li></ul>no00:51:38116What Got You Here Won't Get You There — From Founder-Led Sales to Scalefull<![CDATA["95% of Buying Decisions Are Emotional" — Why Your Sales Team Is Still Selling Logic]]>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 people.

Takeaways

  • Sales 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.

Chapters

  • 00:00 The Role of Sales Coaching
  • 11:52 Emotional Decision Making in Sales
  • 26:52 Becoming a Trusted Advisor
  • 36:08 Neuro-Linguistic Programming (NLP) in Sales
]]>efd66243-0519-4186-a2bf-8590bb7fa25bWed, 15 Apr 2026 14:00:00 GMT<p>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 people.</p><p></p><p>Takeaways</p><ul><li>Sales coaching is about understanding the drivers behind why a person wants to work in a role and aligning their motivations with their career plan.</li><li>Sales managers often only make time to work with individuals when the individual is not performing, leading to a fundamental problem in sales management.</li><li>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.</li></ul><p></p><p>Chapters</p><ul><li>00:00 The Role of Sales Coaching</li><li>11:52 Emotional Decision Making in Sales</li><li>26:52 Becoming a Trusted Advisor</li><li>36:08 Neuro-Linguistic Programming (NLP) in Sales</li></ul>no00:39:20115"95% of Buying Decisions Are Emotional" — Why Your Sales Team Is Still Selling Logicfull<![CDATA[Great Marketing Should Reduce Your Sales Calls]]>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.

Takeaways

  • AI's role in demand generation
  • Shift from lead volume to pipeline velocity

Chapters

  • 00:00 The Modern Demand-Gen Philosophy
  • 10:12 The Impact of AI on Demand Generation
  • 29:46 Operational Efficiency with AI
]]>5135bea2-c40e-47d1-96c2-aa77d93951feWed, 01 Apr 2026 14:39:23 GMT<p>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.</p><p></p><p>Takeaways</p><ul><li>AI's role in demand generation</li><li>Shift from lead volume to pipeline velocity</li></ul><p></p><p>Chapters</p><ul><li>00:00 The Modern Demand-Gen Philosophy</li><li>10:12 The Impact of AI on Demand Generation</li><li>29:46 Operational Efficiency with AI</li></ul>no00:32:34114Great Marketing Should Reduce Your Sales Callsfull<![CDATA[A Champion Isn't a Person — It's a Behavior That Shows Up When There's Good Friction]]>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 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.

Takeaways

  • Champion is a behavior
  • Separating functional roles from behavioral signals
  • Deal management as a separate methodology from sales methodologies Sales enablement should focus on leader enablement
  • Triggering the amygdala is crucial in driving urgency in sales
  • The role of the salesperson is sense-making and providing deep domain expertise to buyers

Chapters

  • 00:00 Redefining Deal Management
  • 07:06 Identifying and Developing Champions
  • 14:23 Behavioral Shifts Throughout the Sales Cycle
  • 21:10 The Purpose of Sales Methodologies and Tech
  • 27:45 Ineffective Leadership Structure
  • 34:50 Neuroscience in Sales and Triggering the Amygdala
]]>0ed4aa7e-0355-4d3e-915b-32cf138215dbThu, 26 Mar 2026 14:03:45 GMT<p>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 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.</p><p></p><p>Takeaways</p><ul><li>Champion is a behavior</li><li>Separating functional roles from behavioral signals</li><li>Deal management as a separate methodology from sales methodologies Sales enablement should focus on leader enablement</li><li>Triggering the amygdala is crucial in driving urgency in sales</li><li>The role of the salesperson is sense-making and providing deep domain expertise to buyers</li></ul><p></p><p>Chapters</p><ul><li>00:00 Redefining Deal Management</li><li>07:06 Identifying and Developing Champions</li><li>14:23 Behavioral Shifts Throughout the Sales Cycle</li><li>21:10 The Purpose of Sales Methodologies and Tech</li><li>27:45 Ineffective Leadership Structure</li><li>34:50 Neuroscience in Sales and Triggering the Amygdala</li></ul>no00:42:51113A Champion Isn't a Person — It's a Behavior That Shows Up When There's Good Frictionfull<![CDATA[Buyer First Is a Behavior, Not a Statement — Carol Mahoney on What Most Companies Get Wrong]]>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
]]>d843fc77-5d39-43e2-9dae-d3a129c4f947Wed, 18 Mar 2026 18:35:06 GMT<p>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.</p><p></p><p>Takeaways</p><ul><li>Buyer-first approach</li><li>AI coaching for sales</li><li>Role of mindset in sales</li></ul><p></p><p>Chapters</p><ul><li>00:00 The Buyer-First Approach</li><li>10:58 AI Coaching for Sales</li><li>18:02 The Role of Mindset in Sales</li></ul>no00:35:16112Buyer First Is a Behavior, Not a Statement — Carol Mahoney on What Most Companies Get Wrongfull<![CDATA["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.

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
]]>f9416b57-5e07-4351-a03d-a4ab526120f4Wed, 11 Mar 2026 14:00:00 GMT<p>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.</p><p></p><p>Takeaways</p><ul><li>Storytelling is a powerful tool in sales</li><li>Soft skills are crucial in the AI marketplace Context is crucial</li><li>Human touch in sales</li></ul><p></p><p>Chapters</p><ul><li>00:00 The Power of Storytelling in Sales</li><li>05:25 The Impact of Soft Skills in Sales</li><li>11:28 The Significance of Soft Skills in AI Marketplace</li><li>19:25 The Role of Soft Skills in Sales and Business Development</li><li>26:08 The Role of Context in AI Processes</li><li>31:10 The Impact of Relationship Building in Business and Sales</li><li>37:39 Structuring Sales Calls and Handling Objections</li><li>45:05 The Future of Sales Process and Buyer's Journey</li></ul>no00:48:48111"AI Will Happily Solve the Wrong Problem Very Efficiently"full<![CDATA["No Decision" Is Not a Close-Loss Reason — Why Your CRM Data Is Lying to You]]>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
]]>5916437c-991a-4076-8095-90aaa6337647Wed, 04 Mar 2026 15:00:00 GMT<p>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.</p><p></p><p>Takeaways</p><ul><li>RevOps evolution</li><li>Conversational intelligence</li><li>Data-driven insights AI and automation in sales operations</li><li>The importance of context and value in sales processes</li></ul><p></p><p>Chapters</p><ul><li>00:00 The Evolution of RevOps</li><li>13:07 Access to Conversations in Sales and Marketing</li><li>22:21 Rethinking CRM and Conversation Stages</li><li>27:38 Effective Signal Identification and Utilization</li><li>33:24 Adoption and Usage of Sales Systems and Processes</li></ul>no00:41:54110"No Decision" Is Not a Close-Loss Reason — Why Your CRM Data Is Lying to Youfull<![CDATA[The Standardization Problem That Shipping Said Was Impossible Got Solved in Two Years]]>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
]]>a7a6b673-5f33-440e-8830-351ad8c8128cWed, 25 Feb 2026 23:44:51 GMT<p>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.</p><p></p><p>Takeaways</p><ul><li>AI adoption in the maritime industry</li><li>Evolution of sales roles and functions</li></ul><p></p><p>Chapters</p><ul><li>00:00 Introduction to Selling AI in Maritime</li><li>07:15 Balancing Industry Expertise and Sales Role</li><li>12:59 Innovative AI Applications in Maritime</li><li>19:30 AI Adoption and Sales Process</li><li>30:22 Future of Sales Roles and AI Adoption</li></ul>no00:33:22The Standardization Problem That Shipping Said Was Impossible Got Solved in Two Yearsfull<![CDATA["If Your Dashboard Isn't Changing Behavior, What's the Point?"]]>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 sales processes. It also explores the tension between sales and marketing and the evolving role of RevOps in go-to-market engineering.

Takeaways

  • RevOps as a strategic function
  • Challenges of scaling revenue without scaling headcount RevOps teams face challenges in driving efficiency and productivity in sales processes.
  • The tension between sales and marketing is a common issue that impacts RevOps teams.

Chapters

  • 00:00 Introduction to RevOps and Chantelle's Background
  • 06:34 The Role of Dashboards in RevOps
  • 17:20 Evaluating Systems and Tools at Asana
  • 28:14 Challenges of Quota and Revenue Attainment
  • 37:16 The Tension Between Sales and Marketing
  • 45:27 The Future of RevOps and Go-to-Market Engineering
]]>50babcba-86af-45d0-ab6b-5a8fd8904934Wed, 18 Feb 2026 16:26:17 GMT<p>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 sales processes. It also explores the tension between sales and marketing and the evolving role of RevOps in go-to-market engineering.</p><p></p><p>Takeaways</p><ul><li>RevOps as a strategic function</li><li>Challenges of scaling revenue without scaling headcount RevOps teams face challenges in driving efficiency and productivity in sales processes.</li><li>The tension between sales and marketing is a common issue that impacts RevOps teams.</li></ul><p></p><p>Chapters</p><ul><li>00:00 Introduction to RevOps and Chantelle's Background</li><li>06:34 The Role of Dashboards in RevOps</li><li>17:20 Evaluating Systems and Tools at Asana</li><li>28:14 Challenges of Quota and Revenue Attainment</li><li>37:16 The Tension Between Sales and Marketing</li><li>45:27 The Future of RevOps and Go-to-Market Engineering</li></ul>no00:48:3518"If Your Dashboard Isn't Changing Behavior, What's the Point?"full<![CDATA["We Are the Picks and Axes" — Selling the Infrastructure That Makes AI Actually Work]]>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
]]>203ee1f8-b5b5-4b76-9056-a8ce4305b789Wed, 11 Feb 2026 20:18:06 GMT<p>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.</p><p></p><p>Takeaways</p><ul><li>Sales Evolution</li><li>AI in Enterprise Sales Buy vs. build scenario</li><li>Changing buying behavior</li><li>Impact of AI on job roles</li></ul><p></p><p>Chapters</p><ul><li>00:00 Evolution of Enterprise Sales</li><li>06:01 Positioning and Sales Process</li><li>11:32 Challenges in Selling AI</li><li>17:55 AI Tools in Sales Leadership</li><li>24:27 Buy vs. Build Scenario and Sales Conversation</li><li>31:31 Competition and Sales Process Challenges</li></ul>no00:40:5517"We Are the Picks and Axes" — Selling the Infrastructure That Makes AI Actually Workfull<![CDATA[The Tools Changed, The Job Didn't: An Enterprise AE's Take on AI in Sales]]>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
]]>b243e17b-caa6-46fe-b3c4-e8d3032127fbWed, 04 Feb 2026 21:47:05 GMT<p>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.</p><p></p><p>Takeaways</p><ul><li>Sales Reps as Conductors</li><li>The Evolution of Enterprise Sales</li><li>The Impact of AI on Sales</li><li>The Role of AI in Maritime Industry</li></ul><p></p><p>Chapters</p><ul><li>00:00 Introduction to Enterprise Sales Evolution</li><li>06:32 Evolution of Sales Techniques</li><li>19:44 Buyer Behavior and AI in Maritime Industry</li><li>30:52 The Future of AI in Sales</li></ul>no00:37:5716The Tools Changed, The Job Didn't: An Enterprise AE's Take on AI in Salesfull<![CDATA[How Enterprise Views Buying AI Products]]>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
]]>7dac9773-aecb-4f31-a5c0-6c7a66a65d4cWed, 28 Jan 2026 19:36:27 GMT<p>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.</p><p></p><p>Takeaways</p><ul><li>Managing multiple stakeholders in enterprise sales</li><li>Transition from restaurant franchise to sales career Storytelling vs. Data</li><li>Stakeholder Management</li></ul><p></p><p>Chapters</p><ul><li>00:00 Introduction to Managing Multiple Stakeholders in Enterprise Sales</li><li>05:43 Comparison of Ad Tech Sales and SaaS Sales</li><li>13:39 ROI Pitch and Objections in Sales Process</li><li>18:50 Data-Driven Play and Handling Objections</li></ul>no00:36:3615How Enterprise Views Buying AI Productsfull<![CDATA[Building a Custom GPT for Every Rep on Your Team]]>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
]]>8f4e303f-83c1-4b0c-bf01-6f1c302259ffWed, 21 Jan 2026 15:00:00 GMT<p>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.</p><p></p><p>Takeaways</p><ul><li>Sales coaching with AI</li><li>Differentiating coaching, training, and feedback</li></ul><p></p><p>Chapters</p><ul><li>00:00 Transition into Sales and Coaching</li><li>06:36 Custom GPT for Sales Coaching</li><li>15:05 Impact of AI on Sales Coaching</li><li>23:41 Mistakes to Avoid in Implementing AI in Sales Coaching</li></ul>no00:27:1714Building a Custom GPT for Every Rep on Your Teamfull<![CDATA["I Just Want to Play More Golf" — Why ROI Isn't Always the Right AI Pitch]]>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 recording solutions, customer perspective on AI in time tracking solutions, and the future of AI in legal tech and sales process.

Takeaways

  • Selling AI in the legal industry
  • AI's impact on time recording and billing efficiency

Chapters

  • 00:00 Introduction to Selling AI in the Legal Industry
  • 09:21 Sales Process Evolution and AI Integration
  • 14:40 Skepticism and Receptiveness to Generative AI Technology in Legal Industry
  • 29:07 Customer Perspective on AI in Time Tracking Solutions
]]>81157637-3d77-4bd6-91bb-7f39d8848957Wed, 14 Jan 2026 17:00:00 GMT<p>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 recording solutions, customer perspective on AI in time tracking solutions, and the future of AI in legal tech and sales process.</p><p></p><p>Takeaways</p><ul><li>Selling AI in the legal industry</li><li>AI's impact on time recording and billing efficiency</li></ul><p></p><p>Chapters</p><ul><li>00:00 Introduction to Selling AI in the Legal Industry</li><li>09:21 Sales Process Evolution and AI Integration</li><li>14:40 Skepticism and Receptiveness to Generative AI Technology in Legal Industry</li><li>29:07 Customer Perspective on AI in Time Tracking Solutions</li></ul>no00:35:3913"I Just Want to Play More Golf" — Why ROI Isn't Always the Right AI Pitchfull<![CDATA[Sales Enablement from Meeting Rooms to CustomGPTs]]>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 sales operations, and the automation of sales roles.

Takeaways

  • Revenue enablement is a growing trend
  • AI has significantly reduced the time and effort required for enablement tasks
  • GPT technology can streamline the creation of customized training materials
  • The combination of enablement and rev ops is essential for data-driven processes
  • AI is reshaping the roles of BDRs and AEs

Chapters

  • 00:00 The Evolution of Sales Enablement
  • 06:02 The Role of Enablement in Sales Training
  • 15:35 Leveraging AI for Personalized Onboarding
  • 25:29 The Synergy Between Sales Enablement and Rev Ops
  • 30:30 The Future of Sales Roles with AI
]]>fae16147-9a7f-466c-b309-cef2c029ed10Thu, 08 Jan 2026 05:45:00 GMT<p>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 sales operations, and the automation of sales roles.</p><p></p><p>Takeaways</p><ul><li>Revenue enablement is a growing trend</li><li>AI has significantly reduced the time and effort required for enablement tasks</li><li>GPT technology can streamline the creation of customized training materials</li><li>The combination of enablement and rev ops is essential for data-driven processes</li><li>AI is reshaping the roles of BDRs and AEs</li></ul><p></p><p>Chapters</p><ul><li>00:00 The Evolution of Sales Enablement</li><li>06:02 The Role of Enablement in Sales Training</li><li>15:35 Leveraging AI for Personalized Onboarding</li><li>25:29 The Synergy Between Sales Enablement and Rev Ops</li><li>30:30 The Future of Sales Roles with AI</li></ul>no00:35:2512Sales Enablement from Meeting Rooms to CustomGPTsfull<![CDATA[The Kickoff]]>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.

]]>bd71c157-321d-41c2-84fd-b1a4c348162eSun, 04 Jan 2026 19:15:19 GMT<p>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.</p>no00:02:1111The Kickofftrailer