Software Sales Simplified: MOVE to Success

Strategic Sales Optimization - SSO

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.com

  1. Ep. 43: AI and the Human Touch for Sales Success - with Guest, Sacha Kupaj

    May 12

    Ep. 43: AI and the Human Touch for Sales Success - with Guest, Sacha Kupaj

    This Week's Episode:This episode features insights from sales expert Sacha Kupaj on mastering enterprise sales, leveraging AI, and building effective team strategies. Discover practical tips on discovery calls, stakeholder management, and adapting to the evolving sales landscape. About our Guest - Sacha Kupaj Sacha Kupaj is a France-born enterprise sales leader based in Austin, who moved to the U.S. in 2018, began his career as an SDR, and has grown into a senior enterprise sales role at Conversica, where he focuses on conversational AI and complex customer engagement. His career reflects a progression from frontline prospecting to enterprise-level selling and hospitality solution leadership, combining hands-on sales discipline, mentorship, competitive research, and a strong belief that AI can improve seller preparation, but trust, curiosity, and human execution still win complex deals. Learn more about Sacha:LinkedIn - LinkedIn Profile Conversica - LinkedIn Page 00:00 Introduction to Software Sales Simplified 01:02 The Role of SDRs in Sales 03:01 Transitioning from SDR to Enterprise Sales 08:59 The Importance of Mentorship in Sales 11:52 AI's Role in Enterprise Selling 16:01 Human Element in Sales 19:46 Collaboration and Team Dynamics in Sales 24:53 Leveraging Team Synergy for Sales Success 27:28 Building Trust and Emotional Connections in Sales 29:18 Effective Communication and Collaboration Strategies 32:19 The Importance of Preparation and Dry Runs 35:01 The Role of Humility and Continuous Learning in Sales 35:35 Navigating Transitions in Sales Roles and Industries 38:41 Understanding the Competitive Landscape in AI Sales 40:36 Leveraging AI for Sales Efficiency and Research 45:43 Advice for Aspiring and Established Sales Professionals 49:04 Like, Follow, and Subscribe! About Software Sales Simplified:Visit us at:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.strategicsalesoptimization.com/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Follow us on Linkedin:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://tinyurl.com/2tcx7mjx⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Send us your questions at ⁠- ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Sales@stratsalesllc.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ "What is a Sales Engineer?" - SSO’s Education Series on YouTube: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.youtube.com/playlist?list=PLxuHbkRfIWtVj_Hg1GYBIg-o5M-icJLn0⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Get Your Copy of "Winning Faster"! Available Here:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.strategicsalesoptimization.com/move-book⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ 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 and 2026. 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.

    49 min
  2. Ep. 42: - Mastering AI Success in Sales for 2026 with Guest, JD Miller Ph.D.

    Apr 22

    Ep. 42: - Mastering AI Success in Sales for 2026 with Guest, JD Miller Ph.D.

    This Week's Episode: In this episode, JD Miller, author of 'The AI Handbook for Sales Professionals,' joins Kevin Donville and Matt Long to explore how AI is transforming sales. They discuss practical applications, ethical considerations, and strategies for leveraging AI to enhance human skills in enterprise sales. About our Guest - JD Miller, Ph.D.: JD Miller Ph.D., is a seasoned executive leader specializing in sales transformations for PE-backed and pre-IPO firms. With six exits and decades of experience in multinational tech companies, he excels in building high-performing teams and implementing rapid growth strategies. As an Operating Advisor for Five Arrows Capital Partners, JD leverages his expertise at the intersection of business, technology, and humanity to strengthen the companies he works with. A frequently-requested conference speaker, JD also shares his roadmap to success in the bestselling book “The CRO’s Guide to Winning in Private Equity.” Learn more about JD Miller PhD at: ⁠⁠https://www.jdmillerphd.com/⁠⁠ JD's Latest Book: The AI Handbook for Sales Professionals: ⁠https://www.example.com/ai-handbook-sales⁠ Additional Resource: AI-Sales-Fail.com: ⁠https://ai-sales-fail.com⁠ Chapters 00:00 Introduction to Ep 42: Talking About AI 01:57 The AI Handbook for Sales Professionals 04:55 Understanding AI in Sales 08:27 Transforming Sales with AI 11:21 The Future of Sales Jobs 13:34 The Risks of Over-Reliance on AI 16:37 Adapting to AI in Sales Careers 20:33 Organizational AI Integration 22:44 Establishing Governance for AI Tools 24:23 Navigating Expertise and Trust in AI 25:52 AI's Role in Enhancing Sales Engineering 27:58 Leveraging AI for Effective Communication 30:15 AI as a Writing Companion 32:40 Synthesizing Data and Ethical Considerations 36:35 Embracing AI: Strategies for Organizations 39:15 The Human Element in AI Integration 47:22 See You Next Episode! About Software Sales Simplified:Visit us at:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.strategicsalesoptimization.com/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Follow us on Linkedin:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://tinyurl.com/2tcx7mjx⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Send us your questions at ⁠- ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Sales@stratsalesllc.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ "What is a Sales Engineer?" - SSO’s Education Series on YouTube: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.youtube.com/playlist?list=PLxuHbkRfIWtVj_Hg1GYBIg-o5M-icJLn0⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Get Your Copy of "Winning Faster"! Available Here:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.strategicsalesoptimization.com/move-book⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ 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 and 2026. 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.

    48 min
  3. Ep 41: Fractional Experts - Sales Success in 2026 with Guest, Andrew Devlin

    Mar 24

    Ep 41: Fractional Experts - Sales Success in 2026 with Guest, Andrew Devlin

    This Week's Episode: This episode explores the rise of fractional leadership, its benefits, challenges, and how organizations can leverage this model for growth. Featuring insights from Andrew Devlin, a seasoned fractional leader, the discussion covers strategic implementation, infrastructure, and the future of fractional roles. About our Guest - Andrew Dev: Andrew Devlin spent 25 years building some of the highest-performing sales organizations in North American technology — leading teams at Cisco, Splunk, Cloudflare, and TELUS that generated over $2 billion in revenue and developed more than 100 sales professionals to President's Club. Recognized as Cisco's Sales Leader of the Year and ranked in the top 1% of global sales leaders, Andrew has a track record of building the kind of sales infrastructure that doesn't just hit quota — it outlasts the people who built it. Today, as President of ScaleTech CRO and a Sales Xceleration Certified Advisor (President's Circle), Andrew works as a Fractional VP of Sales for B2B companies between $10M and $100M — helping founders and CEOs transition from instinct-driven selling to scalable, repeatable revenue. His current clients span Canada, the US, and Australia, with one achieving 192% of quota following a sales infrastructure overhaul. He also teaches B2B Sales at Okanagan College in Kelowna, BC. Andrew's core belief: companies don't fail to scale because they lack salespeople — they fail because they never built the foundation those salespeople need to succeed. Where to Learn More About Andrew: You can find Andrew's profile on LinkedIn: ⁠⁠Andrew Devlin on LinkedIn⁠⁠ Andrew's Website: andrewdevlin.co Chapters 00:00 Introduction to Software Sales Simplified 02:08 Understanding Fractional Leadership 03:53 Andrew Devlin's Journey and Insights 07:50 The Rise of Fractional Leadership 11:38 The Value of Fractional Executives 15:16 Implementing Fractional Leadership Effectively 18:59 Recognizing the Need for Fractional Leadership 22:50 Common Traps for Founders in Scaling 23:51 Building Infrastructure for Success 27:38 Understanding Customer Profiles and Market Dynamics 29:52 The Role of Fractional Leadership 34:35 Navigating Change and Trust in Organizations 43:22 Clarity and Scaling in Business 49:32 See You Next Episode About Software Sales Simplified: Visit us at:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.strategicsalesoptimization.com/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Follow us on Linkedin:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://tinyurl.com/2tcx7mjx⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ 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 Get Your Copy of "Winning Faster"! Available Here:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.strategicsalesoptimization.com/move-book⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ 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 and 2026. 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.

    50 min
  4. Ep 40: Secrets to Scaling Sales Teams with Guest, Mark Krebs

    Mar 2

    Ep 40: Secrets to Scaling Sales Teams with Guest, Mark Krebs

    This Week's Episode: In this episode of Software Sales Simplified: Move to Success, Kevin and Matt catch up with Mark Krebs, a seasoned software sales leader with a diverse background in startups, accounting, and software. They explore the challenges of scaling sales organizations, the importance of process and methodology, authenticity in sales, and the psychological aspects of leadership and startup success. About our Guest - Mark Krebs: Mark Krebs is a seasoned sales and revenue leader with more than 20 years of experience in scaling high-growth software ventures and startup businesses. He currently serves as Vice President of Global Sales at Celebrus, and earlier in his career was part of the founding sales leadership team at OpinionLab, a SaaS company that was acquired by Verint Systems; prior to his SaaS work he trained and practiced as a CPA and senior auditor in Arthur Andersen’s entrepreneurial division. Where to Learn More About Mark / Celebrus: You can find Mark's profile on LinkedIn: ⁠Mark Krebs on LinkedIn⁠ Check out Celebrus here: Celebrus Homepage Chapters 00:00 Introduction to Software Sales Simplified 01:05 Understanding Sales Organizations' Challenges 05:57 Mark Krebs: Insights from Experience 09:33 The Psychology of Sales Leadership 14:40 Navigating Market Maturity and Customer Understanding 18:59 The Importance of Curiosity in Sales 23:59 Identifying Sales Theater 29:24 Metrics and Methodologies in Sales 35:07 Leadership and Accountability in Sales 41:05 Final Thoughts and Advice for Sales Leaders 47:42 Like, Follow, Subscribe - See You Next Episode About Software Sales Simplified: Visit us at:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.strategicsalesoptimization.com/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Follow us on Linkedin:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://tinyurl.com/2tcx7mjx⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ 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 Get Your Copy of "Winning Faster"! Available Here:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.strategicsalesoptimization.com/move-book⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ 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 and 2026. 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.

    48 min
  5. Ep 39: The Secrets to Customer Success in 2026 with Guest, Craig Bloom

    Feb 10

    Ep 39: The Secrets to Customer Success in 2026 with Guest, Craig Bloom

    This Week's Episode: In this episode of Software Sales Simplified: Move to Success, Kevin and Matt sit down with Craig Bloom, an expert in SaaS onboarding and customer success. They explore the importance of customer engagement and alignment between sales and service delivery teams. Craig shares his journey from film and advertising to customer success, highlighting how storytelling strengthens customer interactions. He explains how effective onboarding, proactive engagement, and early alignment on customer objectives improve satisfaction and retention. The conversation also emphasizes how curiosity about a customer’s business leads to better outcomes, with practical advice on fostering a culture of curiosity to drive long-term success. About our Guest - Craig Bloom: Craig Bloom is a post-sale leader operating at the intersection of software sales, onboarding, and customer value. He leads Americas Onboarding at Contentsquare, overseeing enterprise implementations and building the operating rhythms, handoffs, and cross-functional accountability that drive adoption, retention, and expansion. Throughout his career, Craig has led Enterprise Customer Success teams, improved net retention, and partnered closely with Sales and Solutions to align expectations and de-risk delivery. He also brings a background in behavioral analytics from Clicktale and consulting, helping teams identify journey friction and turn insights into measurable improvements. Where to Learn More About Craig: You can find Craig’s profile on LinkedIn: Craig Bloom on LinkedIn Chapters 00:00 Introduction 01:13 The Importance of Engagement 03:27 Meet Craig: A Journey from Storytelling to SaaS 06:04 The Role of Onboarding 08:19 Using Storytelling to Enhance Customer Communication 10:31 Engagement vs. Enablement 12:30 Building Trust Through Curiosity 17:43 The Risk of Poor Engagement 20:50 Creating Effective Engagement 24:26 Bringing in Experts for Effective Execution 25:31 Understanding Customer Objectives 27:43 Building a Maturity Assessment 29:29 The Importance of Communication 30:46 Identifying Implementation Challenges 32:28 Creative Solutions for Resource Constraints 33:51 The Risk of Poor Engagement Plans 36:55 The Role of Communication in Customer Success 39:23 Positioning Professional Services Effectively 42:40 Fostering a Culture of Curiosity 49:51 See you next episode! About Software Sales Simplified: Visit us at:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.strategicsalesoptimization.com/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Follow us on Linkedin:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://tinyurl.com/2tcx7mjx⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ 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 Get Your Copy of "Winning Faster"! Available Here:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.strategicsalesoptimization.com/move-book⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ 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 and 2026. 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.

    50 min
  6. Ep 38: Curiosity and Sales Success in 2026 with Guest, Chris O'Dowd

    Jan 23

    Ep 38: Curiosity and Sales Success in 2026 with Guest, Chris O'Dowd

    This Week's Episode: In this episode of 'Software Sales Simplified', Matt and Kevin engage with Chris O'Dowd, who shares his unique journey from the Marine Corps and FBI to enterprise software sales. The conversation explores the importance of genuine curiosity in sales, the impact of AI on sales processes, and the evolving expectations of buyers. Chris emphasizes the significance of building trust and relationships in sales, continuous learning, and the value of mentorship for new sales professionals. About our Guest - Chris O’Dowd: Chris O’Dowd is a seasoned sales leader and strategic account executive at Quantum Metric, where he partners with some of the world’s largest organizations to turn data-driven insights into better digital products and customer experiences.  With more than a decade of experience in enterprise sales and strategy, Chris brings a unique and diverse background spanning technology, financial services, federal law enforcement, and the military.  Before entering the tech industry, he served as a Special Agent with the FBI, focusing on counterterrorism and human-source recruitment, an experience that shaped his analytical mindset, relentless pursuit of the truth, and ability to lead under pressure. He also spent time in compliance, risk management, and fraud as an audit investigator at UBS Financial Services. He began his career as an Infantry Officer and Operations Officer in the United States Marine Corps. Now based in Nashville, Tennessee, and the father of three girls, Chris is an active member of the local tech community and enjoys engaging with partners and industry groups centered on business intelligence and analytics. Where to Learn More About Chris: You can find Chris’ profile on LinkedIn: ⁠https://www.linkedin.com/in/chrisodowd/ Chapters: 00:00 Introduction to Software Sales Simplified 01:49 Chris O'Dowd's Unique Background 05:30 Transitioning from Military to Sales 09:10 Sales Methodology and Team Dynamics 13:01 The Importance of Curiosity in Sales 15:41 Utilizing Technology in Sales Conversations 19:43 The Value of In-Person Interactions 20:47 The Art of Asking Questions in Sales 23:13 Navigating the Shift to Virtual Sales 26:21 Understanding Buyer Behavior and Expectations 29:07 Leveraging AI in Sales Conversations 31:56 Building Trust in Large Organizations 36:21 Continuous Learning and Adaptation in Sales 39:24 Advice for New Sales Professionals 42:23 Like, Follow, Comment, and Subscribe! See You Soon! About Software Sales Simplified: Visit us at:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.strategicsalesoptimization.com/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Follow us on Linkedin:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://tinyurl.com/2tcx7mjx⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ 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 Get Your Copy of "Winning Faster" Here! ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.strategicsalesoptimization.com/move-book⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ 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 2026. 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.

    43 min
  7. Ep 37. Gen AI Bots: The Hidden Risks with Guest Michael Wasielewski

    12/30/2025

    Ep 37. Gen AI Bots: The Hidden Risks with Guest Michael Wasielewski

    This Week's Episode: In this episode of Software Sales Simplified, Kevin and Matt discuss the complexities and risks associated with AI chatbots, featuring expert Michael Wasielewski. The conversation covers the importance of security, governance, and the potential business risks that come with deploying AI chatbots. Michael shares insights on how organizations can implement effective strategies to mitigate risks while leveraging the benefits of generative AI. The discussion emphasizes the need for a balanced approach that considers both technology and human interaction. About our Guest - Michael Wasielewski: Michael Wasielewski is a seasoned cybersecurity and cloud security leader with over 20 years of experience spanning enterprise IT security, global cloud platforms, and AI risk management. He has held senior roles at organizations including AWS, and Capgemini, where he led global security strategy and helped enterprises adopt cloud and generative AI technologies securely while driving real business outcomes. Today, Michael is the founder of Generative Security, where he focuses on protecting AI-powered applications—especially customer-facing chatbots—by addressing both technical threats and the often-overlooked business risks of generative AI deployment. Where to Learn More About Michael: You can find John’s profile on LinkedIn: ⁠https://www.linkedin.com/in/mwasielewskijr/ Where to Learn More About Generative Security: https://generativesecurity.ai/ Chapters 00:00 Introduction to Software Sales Simplified 02:12 Exploring AI Chatbots in Sales 03:43 Michael Wasielewski's Background in AI Security 07:31 Understanding Risks of AI Chatbots 10:06 Approaches to Implementing AI Chatbots 13:38 The Limitations of AI Understanding 14:34 Defining Guardrails in AI Chatbots 18:14 Agentic vs. Generative AI Workflows 20:17 Malicious Uses of AI Chatbots 23:52 Exploiting AI Chatbots' Intent 25:59 Understanding Competitive Risks in AI 28:59 Governance and Risk Management in AI Deployment 35:00 Business vs. Technology Risks in AI 40:18 The Role of Business Teams in AI Security 49:12 Key Takeaways for AI Implementation 54:59 Like, Follow, Subscribe! See you next episode. About Software Sales Simplified: Visit us at:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.strategicsalesoptimization.com/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Follow us on Linkedin:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://tinyurl.com/2tcx7mjx⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ 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 Get Your Copy of "Winning Faster"! Available Here:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.strategicsalesoptimization.com/move-book⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ 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 and 2026. 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.

    55 min
  8. Ep 36. Empathy & Trust: Unlocking Sales Success. With Guest, John Cavanaugh

    10/02/2025

    Ep 36. Empathy & Trust: Unlocking Sales Success. With Guest, John Cavanaugh

    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/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Follow us on Linkedin:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://tinyurl.com/2tcx7mjx⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ 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 Get Your Copy of "Winning Faster"! Available Here:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.strategicsalesoptimization.com/move-book⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ 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.

    45 min
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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.com

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