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 KupajSacha 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 ProfileConversica - LinkedIn Page00:00 Introduction to Software Sales Simplified01:02 The Role of SDRs in Sales03:01 Transitioning from SDR to Enterprise Sales08:59 The Importance of Mentorship in Sales11:52 AI's Role in Enterprise Selling16:01 Human Element in Sales19:46 Collaboration and Team Dynamics in Sales24:53 Leveraging Team Synergy for Sales Success27:28 Building Trust and Emotional Connections in Sales29:18 Effective Communication and Collaboration Strategies32:19 The Importance of Preparation and Dry Runs35:01 The Role of Humility and Continuous Learning in Sales35:35 Navigating Transitions in Sales Roles and Industries38:41 Understanding the Competitive Landscape in AI Sales40:36 Leveraging AI for Sales Efficiency and Research45:43 Advice for Aspiring and Established Sales Professionals49:04 Like, Follow, and Subscribe!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]⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠"What is a Sales Engineer?" - SSO’s 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 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.