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!

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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.

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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.