When AI and Enterprise Tech Feel Like Magic [Live from AI Summit]

9 snips

Feb 11, 2026

Kapil Gupta, an enterprise AI product and platform leader with two decades at Cigna, Capital One, and Deloitte, talks about making AI usable at scale. He contrasts generative and agentic AI. He discusses governance, fitting tech into existing workflows, legacy data hurdles, and designing products that feel invisible and magical.

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INSIGHT

Generative Vs Agentic Value

Generative AI handles cognitive tasks like drafting and summarizing, while agentic AI completes workflows and outcomes for users.
Agentic AI delivers more tangible value because it performs tasks the user doesn't want to do.

ADVICE

Question And Challenge AI Outputs

Push back, question, and probe AI outputs instead of passively accepting the first answer.
You often unlock more value by shaping the dialogue through follow-up prompts.

ANECDOTE

From 2,000 Attributes To CSV Export

At J.P. Morgan Chase Kapil saw models use 2,000 attributes across millions of customers to draw insights from whole datasets.
At Cigna a user asked for an Excel export and the assistant offered CSV, which revealed practical, controlled behavior at scale.

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Kapil Gupta, former Enterprise AI Product & Platform Leader at Cigna, shares insights from more than two decades of turning cutting-edge technology into enterprise-ready products. He unpacks the difference between generative AI and agentic AI, and why governance, user choice, and thoughtful design matter just as much as innovation.

Learn how enterprises can scale responsibly and why the best technology often feels invisible to the people using it.

Key Takeaways:

The tangible difference between generative AI and agent-based workflows
Why adoption depends on fitting into existing workflows, rather than forcing behavior change
The challenge of legacy systems and disconnected data
How companies can innovate quickly without introducing unnecessary risk
How pushing back, probing, and questioning AI can unlock more value
Why listening to users matters more than building flashy features

Guest Bio: Kapil Gupta is an executive product leader specializing in leveraging emerging technologies to solve complex business problems at scale. As a leader of AI product and platform teams at Cigna and previously at industry leaders like Capital One, Deloitte, and IBM, he has turned breakthrough innovations like Generative AI into practical enterprise solutions.

Kapil is driven by a focus on crafting AI-driven product experiences that solve real problems and ensure high adoption, bridging the gap between sophisticated technology and business value. He balances high-level strategic vision with a passion for staying hands-on, often vibe coding prototypes to prove out new concepts. Kapil holds an MS in Computer Science and an MBA from NYU Stern. He shares his work at kapilgupta.me and lives in New York.

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