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