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Software Sales Simplified: MOVE to Success

Software Sales Simplified: MOVE to Success

Auteur(s): Strategic Sales Optimization - SSO
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 Our show discusses challenges Enterprise and Technical Sales teams encounter every day and creative ways to overcome them. Kevin and Matt have over 50 years experience selling Enterprise Software solutions, running sales teams, leading implementations, and driving consulting practices with some of the biggest companies in the world. Kevin and Matt, authors of "Winning Faster: The MOVE Methodology", share their experiences with listeners and guests; exploring how technology is changing selling, consulting, and business. Visit us at https://www.strategicsalesoptimization.comStrategic Sales Optimization - SSO Économie
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  • Ep 36. Empathy & Trust: Unlocking Sales Success. With Guest, John Cavanaugh

    Ep 36. Empathy & Trust: Unlocking Sales Success. With Guest, John Cavanaugh
    Oct 2 2025
    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/⁠⁠⁠⁠⁠Chapters00:00 Introduction to Software Sales Simplified01:13 Inspirational Sales Leaders02:39 John Kavanagh's Career Journey Begins03:09 The Value of Co-op Programs04:31 Understanding Their Benefits05:04 First Co-op: Learning the Sales Landscape07:08 Navigating Challenges in Early Roles10:53 Transitioning to Sales11:53 Culture Shock at Centra Software14:19 Experiencing Virtual Learning17:12 Learning from Different Personalities19:15 Finding Your Unique Style19:38 The Essence of Effective Selling21:17 The Role of Leadership24:05 Building Trust in Sales Relationships27:33 Navigating the AI Landscape32:18 The Importance of Customer Advocacy33:10 Innovative Sales Training Techniques38:40 Learning from Failures39:45 Advice for Aspiring Sales Professionals45:01 Bye for Now!About Software Sales Simplified:Visit us at:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.strategicsalesoptimization.com/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Follow us on Linkedin:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://tinyurl.com/2tcx7mjx⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Send 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-icJLn0⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Get Your Copy of "Winning Faster"!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.
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    45 min
  • Ep. 35: Recruiting & AI: The Human Factor. Guest - Robyn Gilmartin

    Ep. 35: Recruiting & AI: The Human Factor. Guest - Robyn Gilmartin
    Sep 25 2025
    This Week's Episode:In this episode of Software Sales Simplified, hosts Kevin and Matt discuss the current landscape of hiring and recruitment in the software sales industry with expert Robyn Gilmartin. They explore the impact of AI on recruitment processes, the challenges candidates face in a competitive job market, and the importance of networking and building relationships. Robyn shares insights on how candidates can stand out, the role of experience in hiring, and strategies for companies to streamline their recruitment processes. The conversation also touches on shifting priorities in recruitment and the need for companies to retain top performers.About our Guest - Robyn Gilmartin:Robyn Gilmartin is a seasoned recruiter with nearly 30 years of experience building high-performing teams in the software / SaaS industry. She works directly with executives in growth mode to attract and retain elite GTM talent who consistently outperform. Robyn’s placements don’t just fill roles, they consistently accelerate business outcomes. Her candidates regularly stack rank at the top of their teams, earn Rookie of the Year and President’s Club honors, and advance quickly into leadership.Where to Learn More About Robyn:You can find Robyn’s profile on LinkedIn: ⁠⁠ https://www.linkedin.com/in/robyngilmartin/ You can find ForefrontSearch here: https://www.linkedin.com/company/forefront-executive-search-llc/Chapters00:00 Introduction to Software Sales Insights03:59 Current Trends in Hiring and Recruiting08:07 The Shift from Candidate-Driven to Client-Driven Markets12:06 The Role of AI in Recruitment20:47 Standing Out in a Competitive Job Market24:38 Networking and Building Relationships for Success30:38 The Importance of Storytelling in Interviews32:39 Navigating the Recruitment Landscape35:21 The Reality of Internal Hiring Practices38:10 Age and Experience in the Job Market40:08 Bad Practices in Hiring and Retention43:02 The Evolution of Sales Compensation46:33 Streamlining the Recruitment Process52:35 Like Follow and SubscribeAbout Software Sales Simplified:Visit us at:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.strategicsalesoptimization.com/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Follow us on Linkedin:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://tinyurl.com/2tcx7mjx⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Send 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-icJLn0⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Get Your Copy of "Winning Faster"!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.
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    53 min
  • Ep. 34: Guest Ryan R. Sullivan. Getting it Right: Strategies for Podcast Success

    Ep. 34: Guest Ryan R. Sullivan. Getting it Right: Strategies for Podcast Success
    Sep 17 2025
    This Week's Episode:In this episode of 'Software Sales Simplified', Kevin and Matt engage with podcasting expert Ryan R. Sullivan to explore the significance of podcasting in business, particularly in the realm of software sales. They discuss the benefits of starting a podcast, the importance of identifying a niche, and foundational strategies for success. Ryan shares insights on the complications of corporate podcasting, the value of client interviews, and the role of storytelling in sales. The conversation emphasizes the need for consistency in podcasting and how to leverage content across various platforms. Ryan also introduces a program for businesses to test podcasting before fully committing, highlighting the potential impact of podcasts on personal and professional growth.About our Guest - Ryan R. Sullivan:Ryan makes music, podcasts, and creative strategies. He’s the owner of Podcast Principles, a boutique content strategy and production company for B2B businesses. After his own podcast and music career took off in 2019, he began helping other business owners launch their own. Since then, he’s helped hundreds of founders, entrepreneurs, and multi-platinum artists around the world launch and grow their podcasts and media brands. His mission is to help thousands of business owners expand their reach and revenue through the power of creative podcasting and media.Where to Learn More About Ryan:You can find Ryan’s profile on LinkedIn: ⁠https://www.linkedin.com/in/sullybop/You can check out his podcast here:https://www.linkedin.com/company/podcast-principles/Chapters00:00 Introduction to Software Sales Simplified01:21 The Importance of Podcasting in Business02:24 Ryan Sullivan: Podcasting Expert04:03 Benefits of Starting a Podcast05:58 Identifying Your Niche for Podcasting08:21 Foundational Strategies for Podcast Success10:12 Getting Started with Podcasting12:34 The Evolution of Podcasting Skills13:56 The Market's Role in Podcast Success17:43 Podcasting for Sales Professionals20:28 Navigating Complications in Corporate Podcasting23:30 The Power of Authentic Storytelling26:38 Podcasting vs. Podcast-Style Content29:50 Shifting Focus from Software to Stories32:58 Leveraging Podcast Content Across Platforms38:08 Testing the Waters with Podcasting39:54 Finding Your Voice in Podcasting45:34 See You Next Week!About Software Sales Simplified:Visit us at:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.strategicsalesoptimization.com/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Follow us on Linkedin:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://tinyurl.com/2tcx7mjx⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Send 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-icJLn0⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Get Your Copy of "Winning Faster"!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.
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    46 min
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