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

In this episode, Jack Cochran and Matthew James are joined by Nikhil Sarma, Founder of GTM Solutions Consulting, to explore why customer indecision has become one of the biggest challenges in enterprise sales. They discuss the factors driving buyer hesitation, how to diagnose value clarity vs. organizational issues, and practical strategies for helping customers build the confidence to move forward. Nikhil shares frameworks for understanding stakeholder dynamics, the importance of financial fluency for SEs, and why de-risking the implementation is often more important than the technology itself.

Thank you to Storylane for sponsoring this episode. Get more information at https://www.storylane.io/

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

• Connect with Matthew James: https://www.linkedin.com/in/matthewyoungjames/

• Connect with Nikhil Sarma: https://www.linkedin.com/in/nikhilsarma/

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

• GTM Solutions Consulting: https://www.gtmsolutions.co/

• The Jolt Effect Book: https://www.goodreads.com/book/show/61418641-the-jolt-effect

• The Challenger Sale Book: https://www.goodreads.com/book/show/11910902-the-challenger-sale

• Gartner Research on Buying Team Conflict

1. The Factors Driving Customer Indecision in 2025

2. Value Clarity vs. Organizational Issues

3. Understanding Stakeholder Levels (Operational, Manager, Executive)

4. Discovery as a Two-Way Learning Process

5. Diagnosing and Building Consensus Across Buying Teams

6. De-risking Implementation as a Differentiator

7. Financial Fluency for Presales Professionals

00:00 Welcome
04:45 What's Changed about Customer Buying Behavior
09:50 The Jolt Effect and Challenger Sale Frameworks
13:56 Value Clarity Problems vs. Organizational Issues
20:03 Collaborative Whiteboarding for Discovery
25:17 De-risking Implementation Wins Deals
28:50 How to Connect with Nikhil

In this episode, Jack Cochran and Matthew James are joined by Justin McDonald, Co-founder and CEO of Saleo, to discuss how demo automation technology is transforming the presales landscape. They explore the evolution of presales over the past 20 years, the hidden costs of demo preparation (the "demo tax"), and how AI is revolutionizing how solutions engineers create and personalize demonstrations. Justin shares insights on building relational capital, the importance of in-person meetings, and why the future of presales lies in leveraging technology to spend more quality time with buyers.

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

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

• Connect with Matthew James: https://www.linkedin.com/in/matthewyoungjames/

• Connect with Justin McDonald: https://www.linkedin.com/in/justin-mcdonald-21a3aa6/

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

• Saleo: https://saleo.io/

• Mockaroo (dummy data generator): https://mockaroo.com/

00:00 Welcome

04:24 How has presales evolved over 20 years

09:20 Demo tax

13:37 The importance of in-person meetings

15:55 Breaking down the demo tax components

24:47 AI and Demo Data Agents

26:42 Trends reshaping presales in 2026

1. The Evolution of Presales Technology

   • From manual data creation with tools like Mockaroo to automated demo environments

   • The rise of presales as a respected profession with executive leadership

   • Shift from multi-week prep and constant travel to efficient Zoom-based demos

2. The Demo Prep Tax

   • Multiple departments impacted: DevOps, product, engineering, and SEs

   • Hard dollar costs: hosting demo tenants can cost millions at scale

   • Demo data degradation: perfectly prepared demos degrade over time

   • SE time is expensive, and hours spent on manual data preparation adds up

3. Building Relational Capital

   • Only 17% of sales time is spent with buyers (even less for presales)

   • In-person interactions unlock opportunities that Zoom calls cannot

   • EQ and relationship-building will separate good from great in the age of AI

4. AI-Powered Demo Automation

   • Demo Data Agent: generates personalized demo data with a single prompt

   • Token-based customization for industry, vertical, and use case adaptation

   • Data injection technology allows real-time demo personalization

5. The Future of Presales

   • AI will expand automation across the entire sales cycle

   • Agentic and asynchronous AI tools will support SEs 24/7

   • SEs won't be replaced, their time will be used differently

   • The demo data is the story: great storytelling requires great demo data

In this episode, Jack Cochran and Matthew James are joined by Hannah Bloking, and Allison Macalik, co-founders of 4Under3. They discuss the universal challenge of imposter syndrome in the pre-sales profession, exploring how it manifests, why it affects nearly everyone, and practical strategies to address it. Hannah and Allison share insights from their workshops, including powerful techniques like the "lighthouse speaker" mindset and the importance of naming your imposter to take control of those negative thoughts.

Thank you to Storylane for sponsoring this episode.

Follow the Hosts and Guests

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

• Connect with Matthew James: https://www.linkedin.com/in/matthewyoungjames/

• Connect with Hannah Bloking: https://www.linkedin.com/in/hannahcfrisch/

• Connect with Allison Macalik: https://www.linkedin.com/in/allisonmacalik/

Links and Resources Mentioned

• Storylane: https://storylane.io

• Join Presales Collective: https://www.presalescollective.com/community-overview

• 4Under3: https://4under3.io/

• Email: info@4under3.io

• Follow 4Under3 on LinkedIn: https://www.linkedin.com/company/4under3/

Timestamps

00:00 Opening

03:36 Why Focus on Impostor Syndrome

11:57 The Definition of Impostor Syndrome

14:45 Redefinining as a Phenomenon

20:15 Soft Skills is Important

24:50 The Lighthouse Speaker Mindset

27:15 Zip it, Todd!

Key Topics Covered

1. Understanding Imposter Syndrome

   • The textbook definition: "The persistent inability to believe that one's success is deserved or has been legitimately achieved as a result of one's own efforts or skills"

   • Why it's being reframed as "imposter phenomenon" rather than syndrome

   • How it manifests differently for everyone

   • The discovery that it affects people of all genders, levels, and backgrounds

2. The Presales Connection

   • Why imposter syndrome is particularly prevalent in pre-sales roles

   • The challenge of being asked to be an expert when you're still learning

   • Why internal demos to your own team are the hardest presentations to give

   • The adrenaline rush of presenting and how it relates to imposter feelings

3. Breaking the Silence

   • Why people suffer in silence with imposter syndrome

   • The power of creating space for vulnerability before major initiatives

   • How company culture needs to embrace these conversations

   • The importance of repeat workshops and ongoing dialogue

4. Practical Techniques

   • The Lighthouse Speaker vs. Spotlight Speaker: Thinking of yourself as lighting the way for others rather than being under scrutiny

   • Naming Your Imposter: Giving your negative self-talk a name (like "Todd") to externalize and control it

   • Reframing: Documenting what happens to realize most failures aren't actually about you

   • Finding Your Person: Identifying someone who can hold you accountable when your imposter is talking

5. The Workshop Impact

   • Why companies become repeat customers

   • How addressing imposter syndrome improves productivity and retention

   • The connection between soft skills training and embracing new frameworks

   • Creating internal communities (like AWS's "The Nest") for ongoing support

6. Looking Forward

   • The personal nature of addressing imposter syndrome

   • The importance of daily practice and repetition

   • How workshops facilitate conversations but individuals must do the work

   • The evolving nature of imposter syndrome as AI and change management accelerate

In this episode, Jack Cochran and Matthew James welcome Miriam Graf, a presales veteran with 20 years as an individual contributor and 10 years in leadership roles. Miriam shares invaluable insights on navigating career growth in presales, from speaking up about your aspirations to recognizing when leadership is and isn't the right path for you. She discusses the evolution from being "the hero" to becoming a leader who helps others shine, and explores the diverse career opportunities available beyond traditional management roles.

This episode is sponsored by Elvance. Find out more about them at https://elvance.io/

Follow Us

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

• Connect with Matthew James: https://www.linkedin.com/in/matthewyoungjames/

• Connect with Miriam Graf: https://www.linkedin.com/in/miriamgraf/ or email migraf3@gmail.com

Links and Resources Mentioned

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

• Presales Podcast: https://www.presalescollective.com/podcast

Timestamps

00:00 Welcome

06:53 Lessons to learn earlier

10:38 IC vs leadership

16:42 Expensive experience lessons

22:46 Variety of expertise is good

28:27 Focus on your industry and keep learning

Key Topics Covered

1. Speaking Up About Your Career

   • Why waiting for someone to notice doesn't work

   • How expressing interest puts you on the radar for future opportunities

   • The importance of taking initiative on projects you're passionate about

2. The Transition from Hero to Leader

   • Why being the top SE doesn't automatically translate to leadership

   • The emotional shift from personal accolades to team success

   • Understanding if management is actually the right path for you

3. Alternative Career Paths Beyond Management

   • National expert or technical specialist roles

   • Product management and product marketing opportunities

   • Customer success, implementation, and demo engineering

   • How presales skills translate across multiple disciplines

4. Essential Skills for Career Advancement

   • Soft skills: passion, communication, empathy, and listening

   • Business acumen: understanding the "so what?" for your audience

   • Technical skills: continuous learning and adaptability

5. Learning Through Experience

   • The value of trying roles outside presales

   • How diverse experience makes you a better SE

   • Why failures and tough feedback lead to growth

6. Industry Expertise

   • How to quickly learn an industry's key challenges

   • The value of becoming a vertical expert

   • Building credibility without years of industry experience

In this episode, Jack Cochran and Matthew James are joined by Rob Bruce, a presales leader at Syndigo with 20 years of experience, to discuss an innovative approach to presales operations: the Pursuit Desk. Rob shares how Syndigo has built a dedicated "concierge team" that handles RFPs, security questionnaires, reference coordination, and other time-consuming tasks, freeing solutions engineers to focus on discovery, solutioning, and building customer relationships. The conversation explores how to operate at the "top of your license," the role of AI in scaling pursuit operations, and practical advice for championing similar initiatives at your organization.

Thank you to Elvance for sponsoring this episode: https://elvance.io

Follow Us

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

• Connect with Matthew James: https://www.linkedin.com/in/matthewyoungjames/

• Connect with Rob Bruce: https://www.linkedin.com/in/robbruce/

Links and Resources Mentioned

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

• Book: "Selling is Hard, Buying is Harder" by Garen Hess

Timestamps

00:00 Welcome

04:29 What is a Presales Concierge

11:18 Presales culture

14:00 Working at the top of your diploma

17:10 How do you justify this

21:38 As focused as an F1 team

23:32 AI and the Pursuit Desk

Key Topics Covered

1. The Pursuit Desk Concept

   • Functions as a presales concierge handling non-customer-facing tasks

   • Manages RFPs, InfoSec documents, NDAs, reference coordination

   • Creates centralized control over messaging and responses

   • Operates on a global scale with cultural sensitivity

2. Operating at the Top of Your License

   • Focus on discovery, creative thinking, empathetic listening, and presenting solutions

   • Eliminate time spent on administrative tasks that don't require SE expertise

   • Reduce context switching and multitasking to maintain flow

   • Maximize value delivery to customers and the organization

3. Building the Business Case

   • Find an executive sponsor to champion the initiative

   • Measure impact through deal win rates and velocity

   • Consider creative budget reallocation (travel budgets, etc.)

   • Calculate ROI based on SE productivity and reduced burnout

4. The Role of AI in Pursuit Operations

   • AI handles first-pass RFP responses (80% completion)

   • Pursuit desk personalizes and adds empathy (final 20%)

   • Machine learning analyzes past deals for pattern recognition

   • Go/no-go scorecards based on historical data

   • Enables scaling without proportional headcount increases

5. Presales Culture and Values

   • Building trust through technical expertise and genuine personality

   • Being a "chameleon" who adapts to different buyer needs

   • Creating an environment where people feel welcomed and valued

   • Mentorship and knowledge sharing across teams

6. Preventing Burnout

   • Eliminating nights and weekends spent on RFPs

   • Reducing stress through better task distribution

   • Enabling SEs to focus on work they're passionate about

   • Creating sustainable workloads that retain top talent

7. Measuring Success

   • Tracking time spent on each RFP or pursuit activity

   • Correlating effort to win-loss rates

   • Building audit trails for continuous improvement

   • Creating dashboards for data-driven decision making