Presales Podcast by Presales Collective

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

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

Links and Resources Mentioned
Join Presales Collective Slack: https://www.presalescollective.com/slack

StoryQuadrant: https://storyquadrant.com/

Key Topics Covered
Why Storytelling is an Industrial Skill, Not a Soft Skill

The Story Quadrant Framework: Four Essential Story Types

The Mad Libs Problem in Presales

Discovery as Stepping Into Your Prospect's Story

The Power of Contrast in Creating Memory

What Makes Stories Retellable

Timestamps
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/ 
Follow Us
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/

Links and Resources Mentioned
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

Key Topics Covered
The Factors Driving Customer Indecision in 2025

Value Clarity vs. Organizational Issues

Understanding Stakeholder Levels (Operational, Manager, Executive)

Discovery as a Two-Way Learning Process

Diagnosing and Building Consensus Across Buying Teams

De-risking Implementation as a Differentiator

Financial Fluency for Presales Professionals

Timestamps
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

The State of Presales and Demo Technologies, and What's Coming in 2026
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.
Follow Us
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/ 

Links and Resources Mentioned
Join Presales Collective Slack: https://www.presalescollective.com/slack

Saleo: https://saleo.io/

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

Timestamps
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
Key Topics Covered
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


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


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


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


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: [email protected]

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
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


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


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


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


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


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

Episode 181: Charting Your Presales Career Path with Miriam Graf
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 [email protected]

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
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


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


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


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


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


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