Selling AI

Warren Kucker

Sellers learning from sellers how to navigate the new world of selling AI, with AI.

  1. 4d ago

    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 AISales behavior impactCRM 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 Strategy09:40 Deal Qualification and Strategic Sales Approaches23:28 Sales Pipeline Management Challenges29:20 Impact of AI on Sales Processes36:37 Analytical Approach to Sales Process GTM Science Podcast: Spotify: Here & Apple: Here GTM Efficiency Pyramid Framework: HereGTM  Metrics Framework: Here GTM Science Newsletter: Here Eddie Reynolds' LinkedIn: Here

    46 min

  2. May 20

    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

    28 min

  3. May 13

    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 assistantHuman connection becomes more valuable in the AI era Personalized software solutions for small businessesThe future of work in a world with AI and automation Chapters 00:00 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

    43 min

  4. May 6

    "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 SellingChannel Complexity Sales ProcessMarket ExpansionAI in Furniture IndustryTrends in Office Space Utilization Chapters 00:00 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

    40 min

  5. Apr 29

    "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 implementationLeveraging the metric engine for AI in sales AI's impact on sales motions and data insightsChallenges and opportunities in AI adoption and implementation Chapters 00:00 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

    45 min

  6. Apr 22

    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 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 it Chapters 00:00 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

    52 min

  7. Apr 15

    "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 Coaching11:52 Emotional Decision Making in Sales26:52 Becoming a Trusted Advisor36:08 Neuro-Linguistic Programming (NLP) in Sales

    39 min

  8. Apr 1

    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 generationShift from lead volume to pipeline velocity Chapters 00:00 The Modern Demand-Gen Philosophy10:12 The Impact of AI on Demand Generation29:46 Operational Efficiency with AI

    33 min
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Sellers learning from sellers how to navigate the new world of selling AI, with AI.

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  • Creator
    Warren Kucker
  • Years Active
    2K
  • Episodes
    21
  • Rating
    Clean
  • Copyright
    © 2026 Warren Kucker
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    Selling AI