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.
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