This Week's Episode:
In this episode of Software Sales Simplified, hosts Kevin and Matt sit down with John Cavanagh, a seasoned sales professional, to explore the intricacies of software sales, the importance of mentorship, and the evolving landscape influenced by AI. John shares his career journey, highlighting the significance of internships (co-op programs), the value of understanding customer needs, and the qualities of effective sales leaders. The conversation delves into the necessity of empathy in sales, the role of training and role-playing, and the challenges posed by AI in the sales process. John emphasizes the importance of building trust and nurturing relationships in achieving long-term success in sales; success which John stresses requires a seller to remain curious to be effective.
About our Guest - John Cavanaugh:
John Cavanaugh 20 year software sales veteran, primarily in the online learning and HR Tech space. He works with customers to understand business challenges and form a collaborative approach to solve them. A multiple time President’s Club member, he started his career in pre-sales and sales operations before moving to enterprise sales 20 years ago. He currently serves as a Sr. Enterprise Account Executive at Attensi. Attensi is a bleeding edge provider of bespoke situational gaming simulations designed to be immersive, fun, and engaging. The outcomes are enabling behavior change at scale, increasing employee confidence, and measurable business impact.
Where to Learn More About John:
You can find John’s profile on LinkedIn: https://www.linkedin.com/in/johncavanaugh/
Chapters
00:00 Introduction to Software Sales Simplified
01:13 Inspirational Sales Leaders
02:39 John Kavanagh's Career Journey Begins
03:09 The Value of Co-op Programs
04:31 Understanding Their Benefits
05:04 First Co-op: Learning the Sales Landscape
07:08 Navigating Challenges in Early Roles
10:53 Transitioning to Sales
11:53 Culture Shock at Centra Software
14:19 Experiencing Virtual Learning
17:12 Learning from Different Personalities
19:15 Finding Your Unique Style
19:38 The Essence of Effective Selling
21:17 The Role of Leadership
24:05 Building Trust in Sales Relationships
27:33 Navigating the AI Landscape
32:18 The Importance of Customer Advocacy
33:10 Innovative Sales Training Techniques
38:40 Learning from Failures
39:45 Advice for Aspiring Sales Professionals
45:01 Bye for Now!
About Software Sales Simplified:
Visit us at: https://www.strategicsalesoptimization.com/
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Send us your questions at - Sales@stratsalesllc.com
"What is a Sales Engineer?" - Education Series on YouTube:
https://www.youtube.com/playlist?list=PLxuHbkRfIWtVj_Hg1GYBIg-o5M-icJLn0
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Why 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.
