
Startup & Sales Podcast
Startup & Sales Podcast
Selling AI
Selling AI
Join us as we explore the intersection of artificial intelligence and sales, delving into the strategies, tools, and stories from professionals who are leveraging AI to sell smarter and selling AI products that are reshaping the future of go-to-market.
Join us as we explore the intersection of artificial intelligence and sales, delving into the strategies, tools, and stories from professionals who are leveraging AI to sell smarter and selling AI products that are reshaping the future of go-to-market.
Recent Episodes
Recent Episodes
EP. 12
Buyer First Is a Behavior, Not a Statement — Carol Mahoney on What Most Companies Get Wrong
Mar 18, 2026
35 minutes
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

EP. 12
Buyer First Is a Behavior, Not a Statement — Carol Mahoney on What Most Companies Get Wrong
Mar 18, 2026
35 minutes
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

EP. 12
Buyer First Is a Behavior, Not a Statement — Carol Mahoney on What Most Companies Get Wrong
Mar 18, 2026
35 minutes
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

EP. 11
AI Will Happily Solve the Wrong Problem Very Efficiently
Mar 11, 2026
47 minutes
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

EP. 11
AI Will Happily Solve the Wrong Problem Very Efficiently
Mar 11, 2026
47 minutes
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

EP. 11
AI Will Happily Solve the Wrong Problem Very Efficiently
Mar 11, 2026
47 minutes
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

EP. 10
"No Decision" Is Not a Close-Loss Reason — Why Your CRM Data Is Lying to You
Mar 3, 2026
41 minutes
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

EP. 10
"No Decision" Is Not a Close-Loss Reason — Why Your CRM Data Is Lying to You
Mar 3, 2026
41 minutes
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

EP. 10
"No Decision" Is Not a Close-Loss Reason — Why Your CRM Data Is Lying to You
Mar 3, 2026
41 minutes
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

EP. 9
The Standardization Problem That Shipping Said Was Impossible Got Solved in Two Years
Feb 25, 2026
33 minutesx
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

EP. 9
The Standardization Problem That Shipping Said Was Impossible Got Solved in Two Years
Feb 25, 2026
33 minutesx
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

EP. 9
The Standardization Problem That Shipping Said Was Impossible Got Solved in Two Years
Feb 25, 2026
33 minutesx
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

EP. 8
"If Your Dashboard Isn't Changing Behavior, What's the Point?"
Feb 18, 2026
48 minutes
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

EP. 8
"If Your Dashboard Isn't Changing Behavior, What's the Point?"
Feb 18, 2026
48 minutes
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

EP. 8
"If Your Dashboard Isn't Changing Behavior, What's the Point?"
Feb 18, 2026
48 minutes
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

Our Host
Our Host
Warren Kucker
Background:
Warren Kucker is a seasoned revenue leader and serial entrepreneur with a track record of building and scaling go-to-market operations from the ground up. As the Founder and CRO of Basiq.work, he's at the forefront of conversational AI, helping sales teams, product leaders, and engineers turn meetings into actionable workflows. Before founding Basiq, Warren served as a 2x VP of Sales and CRO at Series B vertical tech companies, including tab32 and Sedna, where he consistently scaled revenue from founder-led sales to $2M+ in quarterly bookings.
Warren's entrepreneurial journey includes two successful exits: Shelly.ai, a machine-learning platform that automated email workflows, and Boxton, an early-stage digital freight platform serving Fortune 500 procurement teams. His career began at Apple, where he built and managed a $100M program focused on efficient ad-hoc shipment management.
Expertise:
Warren brings deep expertise in revenue operations, AI-powered sales intelligence, and building high-performance GTM teams to the podcast. He's passionate about exploring how AI is transforming the way we work—particularly the evolution from data collection to action orchestration. With hands-on experience scaling startups, implementing buyer enablement strategies, and driving operational efficiency, Warren offers practical insights on moving from "heroic effort" to scalable systems. His philosophy is simple: close the gap between conversation and action.
Interests:
Beyond his ventures in sales and AI, Warren is deeply invested in the future of work and how technology can augment human performance rather than replace it. He's an active voice in the sales leadership community, regularly sharing lessons learned from building companies and scaling teams. Warren believes the future of AI isn't more tools—it's better human interactions. Based in San Diego, he's currently building Basiq with "some of the coolest people on the planet" toward a $10M ARR milestone.

