Jaydeep Chakrabarty - The Test Tribe
Session

The almost right machine: How to test, trust, and ship software built with AI

Outline

What we’ll cover in this session.

“Software development has quietly crossed a line. The hard part is no longer always writing the first version of code. Code, test cases, product flows, documentation, and prototypes can now be generated at remarkable speed. That is progress. But it creates a new quality problem: software that does not look broken. It compiles, runs, passes the demo, clears basic checks, and still may be wrong. Not completely wrong, but almost right. It may misunderstand business intent, miss the real context, ignore a constraint, or fail only when the consequence is high. This session is about quality engineering when software is created at AI speed, and why traditional pass/fail thinking is no longer enough.
We’ll walk through
01
Why faster software creation changes the meaning of quality⁠
02
Why the biggest risk is not always broken software, but almost-right software
03

How AI-generated code, tests, flows, and documentation change the review and testing mindset

04
Why QAs, engineers, PMs, and AI teams need to move beyond binary asserts
05
A simple quality lens: Correctness, Context, Constraints, Confidence, and Consequence
05
A simple quality lens: Correctness, Context, Constraints, Confidence, and Consequence
07

How this lens helps teams validate intent, assumptions, and risk before software reaches production”

Speaker

Jaydeep Chakrabarty

Head of AI in Tech

Piramal Finance logo
Jaydeep Chakrabarty is currently serving as the Director of AI in Tech at Piramal Capital & Housing Finance Limited, based in Bengaluru, Karnataka. With an extensive 18-year career spanning diverse roles such as Fullstack Developer, Infrastructure Developer, Experience and Visual Designer, Project Manager, Quality Analyst, Security Specialist, and Data Scientist, Jaydeep brings a comprehensive technological perspective to his leadership role.

Before joining Piramal Finance, Jaydeep was the Head of Generative AI Engagements and R&D and Head of Communities at Thoughtworks India. At Thoughtworks, he founded and led the Generative AI group “GPT Wizards,” driving research, development, and client partnerships across India, the Middle East, and other global regions. His strategic initiatives significantly contributed to revenue growth by successfully implementing generative AI solutions.

An avid open-source enthusiast, Jaydeep has contributed to notable projects including Talisman, OpenStack, Report-mine, Taiko, and EEG studies. He regularly shares his insights through prestigious publications such as EFY (Electronics For You), Opensource4You, and The Hindu’s tech column “Text and Context – Toolbox.”

Jaydeep’s expertise lies in bridging theoretical advancements in artificial intelligence with practical applications, emphasizing ethical considerations and real-world impact. His current role at Piramal Finance involves integrating AI into critical organizational functions such as credit underwriting and sales enablement.

Recognized as a thought leader in AI innovation and implementation, his contributions have earned him several prestigious recognitions, including the Asia’s Leadership Award 2025, where he was named a “Top Visionary Making a Wave in 2025.” In addition, he was honored as the Best Tech Influencer at the 2nd IT Confex in Dubai in October 2024 and was featured by Insights Success magazine as one of the most impactful and visionary personalities to watch in 2025. He is also a frequent speaker at industry conferences and events, addressing topics related to generative AI, ethical AI deployment, agile methodologies, and emerging technologies.

Catch this session live.

One pass, every talk, no parallel tracks. Super Early Bird
ends when the next 200 seats are gone.

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