Ep. 16: Guest Josh Gillespie - The AI Revolution: Opportunities and Pitfalls

This Week's Episode: Kevin and Matt engage with Josh Gillespie, Head of Growth at Aomni, discussing his journey from philosophy major to sales leader in the AI space. They explore the importance of research in sales, the challenges of discovery calls, and the growth strategies for startups. Josh shares insights on leveraging technology for sales success and the evolving landscape of AI in the industry. In this conversation, Josh Gillespie shares insights on the realities of startup life, the evolving landscape of AI companies, and the challenges faced by sales professionals in this new era. Their discussion also covers innovation and practicality in sales strategies, especially in the context of AI's rapid growth.This Week's Guest:Josh Gillespie is a seasoned sales professional dedicated to helping underserved communities enter the tech industry. Based in the San Francisco Bay Area, he provides pro bono training at AlwaysHired Sales Bootcamp for first-time tech and sales applicants. As a founding Account Executive at PandaDoc, he helped grow the company from zero to $90 million in annual recurring revenue, and went on to hold key roles at Glassbox and Yelp. A former philosophy student turned SaaS sales expert, Josh also founded “Losing by Design” and is an avid basketball fan, husband, father, and dog owner. He continues to mentor others in tech, leveraging his extensive experience and network.How to Find out More About Josh:You can find Josh's profile on LinkedIn, or on the Aomni website: https://www.aomni.com/share/people/434b54e2-78ca-4379-9fc8-02187e507b22Chapters:00:00 Introduction to Software Sales Simplified00:28 Meet Josh Gillespie: A Unique Sales Journey03:58 Transitioning to AI Sales: Embracing Change06:51 Understanding Omni: The Research Solution for Sellers10:12 The Importance of Research in Sales13:57 Discovery Calls: Building Trust and Understanding Needs16:38 Growth Challenges in a Startup Environment19:43 Startup Life: The Reality of Sales in Startups22:07 The AI Boom: Opportunities and Challenges25:42 Navigating the AI Landscape: Key Considerations29:06 The Role of AI in Sales: Myths vs. Reality35:02 The Future of Sales Leadership in an AI World43:37 Comment, Like, Subscribe, Follow!About Software Sales Simplified:Visit us at:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠https://www.strategicsalesoptimization.com/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Follow us on Linkedin:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠https://tinyurl.com/2tcx7mjx⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Send us your questions at ⁠- ⁠⁠[email protected]⁠⁠⁠Get Your Copy of "Winning Faster"!Order your own copy of, "Winning Faster: The MOVE Framework for Enterprise Software Sales" on our website or on Amazon.Available Here:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.strategicsalesoptimization.com/move-book⁠⁠⁠⁠⁠⁠⁠⁠Why Listen to Software Sales Simplified?Make Software Sales Simplified: MOVE to Success, your go-to podcast for mastering enterprise software sales through authentic customer engagement and actionable consulting insights. Join us for each episode as we break down proven strategies and real-world experiences to help you build trust, close deals, and drive long-term success along your Enterprise Software Sales or Consulting journey.Copyrighted Broadcast:Thank you for tuning in to Software Sales Simplified: MOVE to Success. This podcast is produced by and is the sole property of Strategic Sales Optimization LLC, copyright 2025. Reproduction or use of this broadcast in whole or in part without express written permission from Strategic Sales Optimization LLC is strictly prohibited. All rights reserved.