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💡 AI is not just a tool anymore. It is reshaping how companies are evaluated, how risk is assessed, and how technology leadership creates enterprise value. In diligence, product strategy, and organizational design, AI is compressing timelines while raising the bar for judgment. In this episode of AI with Bry, we unpack what responsible AI adoption looks like inside real companies. This conversation is about cutting through AI theater, understanding where automation accelerates value, and recognizing where seasoned leadership still matters most. For founders and investors, the tension is clear. AI can speed up analysis and reporting, but it cannot replace wisdom, context, and experience. That distinction matters now more than ever. I’m joined by Greg Smith, a fractional CTO and technology strategist at TechCXO. Greg leads product and technology practices focused on tech diligence, executive leadership, and organizational transformation. With decades of experience as an operator, founder, and executive, he brings a grounded view on how AI should be embedded into real workflows without replacing critical thinking. His perspective sits at the intersection of investors, boards, and executive teams navigating high stakes decisions. We explore how AI is changing tech diligence from information gathering to reporting, where it adds leverage, and where it introduces risk. If you are responsible for scaling a company, investing capital, or leading technical teams, this episode will help you think more clearly about execution in an AI accelerated world. ✨ In This Episode, You’ll Learn How AI accelerates tech diligence without replacing executive judgment Why grassroots AI adoption outperforms top down mandates Where investors can overestimate AI generated diligence reports How leadership must hold AI accountable the same way it holds teams accountable Why developer roles are shifting toward product thinking How to evaluate whether a company’s AI claims create real differentiation What technical moat means in a world of compressed development cycles Why wisdom and experience remain strategic advantages 👤 Connect with Greg Smith https://www.techcxo.com/partners/greg... LinkedIn / fractionalcto 🧰 Tools, Platforms, and Concepts Mentioned AI Models and Assistants ChatGPT https://chat.openai.com Claude by Anthropic https://www.anthropic.com/claude Research and Knowledge Tools NotebookLM by Google https://notebooklm.google.com Development or Execution Tools OpenAI API https://platform.openai.com Microsoft Azure AI https://azure.microsoft.com/en-us/pro... Industry or Concept References Tech Diligence Fractional CTO Leadership SOC 2 Compliance 🚀 Watch and Follow AI with Bry 🎧 Full episodes + show notes: https://bry.net/ai ▶️ YouTube: / @aiwithbry 📸 Instagram: / aiwithbry 📘 Facebook: https://www.facebook.com/profile.php?... 🎵 TikTok: / aiwithbry.com 🐦 X: https://x.com/aiwithbry 💼 LinkedIn: / phingers #aiwithbry #aileadership #futureofwork #techdiligence #fractionalcto #venturecapital #privateequity #aiexecution #productleadership #innovation