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Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google & Amazon

Building AI products is not just an evolution of traditional software development—it's a paradigm shift that demands new methodologies, mindsets, and leadership approaches. With real-world experience from leading AI initiatives at top tech companies, Aishwarya Naresh Reganti and Kiriti Badam share hard-earned insights on what actually works when bringing AI systems to market.
AI products differ fundamentally from traditional software due to their non-deterministic behavior and the delicate balance between agency and control. Success requires starting with low-autonomy systems under strong human oversight, then iteratively increasing automation as reliability improves. Effective teams prioritize problem-first design, tight cross-functional collaboration, and CEO-level engagement with AI tools. The Continuous Calibration/Continuous Development (CC/CD) framework enables safer deployment by using real-world data to refine system behavior and uncover hidden edge cases. While evaluations (evals) are useful, they're insufficient without production monitoring and customer feedback. Overhyped trends like multi-agent systems often fail in practice, whereas coding agents remain underutilized but high-potential. Ultimately, long-term advantage comes not from technology alone, but from organizational persistence, deep user understanding, and the ability to continuously adapt as models and workflows evolve.
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AI systems are non-deterministic and act as black boxes, sensitive to prompt variations
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Begin with AI assisting humans in customer support to gather feedback before increasing autonomy.
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74-75% of enterprises cite reliability as their biggest challenge in deploying customer-facing AI
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Prompt injection and jailbreaking are potentially unsolvable problems in AI security
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The CEO's interaction with AI tools is the top predictor of success.
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Independent benchmarks are model evals, not application evals
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Evals alone are not sufficient for measuring AI product success
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57:31
CC/CD is the AI version of CI/CD, focusing on evals, analysis, and iteration
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User behavior consistency is a critical indicator for framework progression
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1:04:17
Being obsessed with the business problem is more valuable than constantly building with new tools.
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Combining image models, LLMs, and world models will be a significant area of development
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1:11:42
The pain of iterating through AI development becomes a company's new moat
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1:19:22
Believe in yourself even when data suggests failure.