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/Chapters00:00 Introduction to Software Sales Simplified02:12 Exploring AI Chatbots in Sales03:43 Michael Wasielewski's Background in AI Security07:31 Understanding Risks of AI Chatbots10:06 Approaches to Implementing AI Chatbots13:38 The Limitations of AI Understanding14:34 Defining Guardrails in AI Chatbots18:14 Agentic vs. Generative AI Workflows20:17 Malicious Uses of AI Chatbots23:52 Exploiting AI Chatbots' Intent25:59 Understanding Competitive Risks in AI28:59 Governance and Risk Management in AI Deployment35:00 Business vs. Technology Risks in AI40:18 The Role of Business Teams in AI Security49:12 Key Takeaways for AI Implementation54:59 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/2tcx7mjx⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Send us your questions at ⁠- ⁠⁠⁠⁠⁠⁠⁠⁠[email protected]⁠⁠⁠⁠⁠⁠⁠⁠⁠"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 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.