In this episode, Jack Cochran is joined by Nalin Senthamil, Founder and CEO of Storylane, to discuss the evolution of AI in presales beyond simple demo automation. They explore the hidden costs of demos, how the buyer themselves are becoming AI-powered, and the emergence of AI tools for sellers, much like Storylane has developed with RepEx

Thank you to Storylane for sponsoring this episode! Visit Storylane.io to learn more.

• Connect with Jack Cochran: https://www.linkedin.com/in/jackcochran/

• Connect with Nalin Senthamil: https://www.linkedin.com/in/nalinpradeep/

• Join Presales Collective Slack: https://www.presalescollective.com/slack

• RepEx (AI buyer engagement platform): Available at https://www.storylane.io/

1. Nalin's Journey from Amazon AI Engineer to Demo Automation Founder

2. The Hidden Cost Per Demo

3. AI at the Infrastructure Level

4. RepEx: The Next Generation of Buyer Engagement

5. The Context Handoff Problem

6. Presales as Strategic Advisors in 2026

00:00 Welcome

03:15 Nalin's Background: From Amazon AI Engineer to Storylane Founder

05:54 The Cost Per Demo Problem and Demo Automation Impact

13:24 What are we leaving behind with AI, and what remains human?

20:00 RepEx Launch: Beyond Traditional Chatbots

26:25 The Importance of Context in the Buyer Journey

28:54 How Presales Teams Can Prepare for AI Integration

30:15 Final Advice: Building Long-Term AI Capabilities in Presales

In this episode recorded at the Presales Collective Leadership Next Summit in November of 2025, Jack Cochran sits down with Gretchen Fitzgibbons, Senior Manager of Strategic Solutions Consulting at Airtable, to discuss what it means to be a courageous leader in presales. They explore how to make difficult decisions under pressure, navigate organizational politics with integrity, and build the support systems that enable consistent leadership. Gretchen shares powerful stories from her two decades of experience advising Fortune 500 customers and leading presales teams, including standing up for a team member being unfairly assessed and creating win-win solutions in challenging situations.

• Connect with Jack Cochran: https://www.linkedin.com/in/jackcochran/

• Connect with Gretchen Fitzgibbons: https://www.linkedin.com/in/gretchenfitzgibbons/

• Join Presales Collective Slack: https://www.presalescollective.com/slack

• Sol/Con 2026: https://www.presalescollective.com/solcon-2026

• Book mentioned: Think Again by Adam Grant: https://adamgrant.net/book/think-again/

• Book mentioned: Thinking, Fast and Slow by Daniel Kahneman: https://www.goodreads.com/book/show/11468377-thinking-fast-and-slow

1. Redefining Courage and Leadership

2. Making Tough Calls: Standing Up for Team Members

3. Focusing on Your Team rather than on Yourself

4. How to Prepare for a Leadership Role

5. It's OK to be Wrong

6. Developing Your Leadership Skills

7. Grounding Principles for Leadership

00:00 Welcome and Introduction

02:14 Defining Courage and Leadership in Presales

05:15 Making Tough Calls: A Story of Standing Up for What's Right

11:20 Focusing on Your Team rather than on Yourself

22:07 How to Prepare for a Leadership Role

27:40 It's OK to be Wrong

30:30 Developing Leadership Skills

37:42 Final Takeaways and Grounding Principles

In this episode, Jack Cochran is joined by Jon Billett, Founder and CEO of StoryQuadrant, to discuss why storytelling in presales needs to be treated as an industrial skill rather than a soft skill. They explore Jon's framework for the four types of stories every SE should master, the danger of "Mad Libs" style customer stories, and why the most important story is the one told after you leave the room. Jon shares insights from his 15 years in presales and his unique background as a member of the Magic Circle, revealing how structure, rather than content, creates memorable presentations that drive deals forward.

• Connect with Jack Cochran: https://www.linkedin.com/in/jackcochran/

• Connect with Jon Billett: https://www.linkedin.com/in/jbillett/

• Join Presales Collective Slack: https://www.presalescollective.com/slack

• StoryQuadrant: https://storyquadrant.com/

1. Why Storytelling is an Industrial Skill, Not a Soft Skill

2. The Story Quadrant Framework: Four Essential Story Types

3. The Mad Libs Problem in Presales

4. Discovery as Stepping Into Your Prospect's Story

5. The Power of Contrast in Creating Memory

6. What Makes Stories Retellable

00:00 Welcome

03:16 Jon's Journey to Storytelling

06:31 Storytelling as an Industrial Skill

09:23 Overcoming the Belief: "I'm Not a Good Storyteller"

12:24 The Success Story Trap

15:59 The Mad Libs Formula Problem

18:13 Discovery Stories: Stepping Into Their World

21:20 Maximizing Your 5% of Face Time

23:10 Your Story: The Four-Minute Trust Window

26:51 Positioning Stories: Nobody Cares About Your Offices

27:40 The Story They Tell

30:30 One Technique to Implement Tomorrow: The Power of Contrast