From “Black Box” to Business Breakthroughs: Sid Banerjee on AI, Customer Experience & The Future of Agency

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What happens when a billion-dollar founder who was building “AI” before it was even a buzzword sits down to talk about where it’s all headed?

In this episode of The AI CEO Podcast, host Seema Alexander welcomes Sid Banerjee—founder of Clarabridge (acquired for $1B), former Chief Strategy Officer at Medallia, and Board Chair of Prolific—to unpack the future of customer experience, the rise of agentic AI, and the leadership mindset shifts every CEO will need to make.

Sid reveals why AI today still operates like a “black box” and why transparency, data stitching, and multi-tech collaboration will define the next era. He shares the aha moment that changed how he saw AgTech, and why giving AI “true agency” could fundamentally reshape entire industries.

But this isn’t just about technology—it’s about responsibility. Sid warns of AI’s dual-edged nature: its ability to increase profitability and efficiency, but also its potential to erode human connection or enable addictive, harmful experiences.

From real-world Clarabridge case studies to the coming bot-to-bot economy, and from personalized hospitality experiences to why governance can’t wait 10 years, this conversation is a masterclass in building with foresight, precision, and impact.

You’ll learn:

• Why AI customer experiences still “suck” and how to fix them

• The difference between tasks, to-dos, and true agentic action

• How to move from lagging metrics to leading indicators in CX

• The 4-part ROI framework for AI adoption

• When AI adoption will actually cross the chasm—and where first

TIMESTAMPS:
00:00 Intro
01:47 Meet Sid Banerjee
04:39 Why customer experience is still broken
10:45 The role of agentic AI
13:44 Clarabridge: Building before the AI hype
23:26 AI’s evolution in business
35:08 Precision + personalization in decision-making
38:25 The future of hospitality and personalization
41:23 Mattel, OpenAI & the ethics of AI in toys
45:14 Why AI governance can’t wait
50:39 Data privacy & security
55:03 The ROI framework for AI projects
58:44 Future predictions & rapid fire

Connect with Sid:
LinkedIn: Sid Banerjee
Medallia: Sid’s Author Page

Connect with Seema:
Virgent AI: virgent.ai
Disruptive CEO Advisory: disruptive.ceo
LinkedIn: Seema Alexander
Instagram: @seemaalexander

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Production Studio: Legacy Sessions

Is this the end of work as we know it? Or the beginning of a new kind of freedom?

In this provocative episode of The AI CEO Podcast, host Seema Alexander sits down with Catherine McMillan, founding director of the AI Collective — a global grassroots movement redefining the role of humans in the age of AI.

What started in a living room is now a 70,000+ member movement across 25 cities and 7 countries, united by one mission: to center humanity in the AI revolution.

Together, Seema and Catherine unpack:

• The moment Catherine knew ChatGPT was the “end of work as we know it”

• Why today’s students feel betrayed by traditional career paths

• How AI is erasing critical thinking — and what we must protect

• Why “taste, agency, and relationships” will define the next generation of leaders

• The real reason we need a new education system NOW

This episode will challenge how you think about the future of work, technology, and your own role in shaping it.

👇 Whether you're a founder, policymaker, or just AI-curious — don’t miss this one.

• How AI is quietly collapsing traditional white-collar paths

• Why “digital natives” see this as the next civil rights movement

• The 3 human traits that AI can’t replace — and how to sharpen them

• How grassroots AI communities like AI Collective are shaping global policy and innovation

• (00:00) Intro & setup

• (01:54) Who is Catherine McMillan?

• (04:30) Origin of the AI Collective (70K members globally)

• (10:55) The moment ChatGPT changed everything

• (21:56) Why taste, agency, and human connection matter more than ever

• (28:00) Education, creativity, and what we’re doing wrong

• (43:15) Why this isn’t just tech — it’s a humanity mission

Catherine McMillan
🌐 AI Collective
🔗 LinkedIn

Seema Alexander
AI is Rewriting Business. I Work with CEOs Who Refuse to Be Disrupted—Ready to Lead in the AI Era. I speak, educate and build AI solutions to accelerate AI Adoption in businesses and industry safely and responsibily.

🌐 Host, The AI CEO Podcast
📈 Disruptive CEO Advisory
📲 LinkedIn
📸 Instagram

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📢 Share this with a founder or business leader who needs to hear it

⚠️ If you think legal can wait until launch—you’re already behind.

In this episode of The AI CEO, I sat down with powerhouse attorneys Ambur Smith (Founder, Ambur Smith Law) and Cameron Powell (Founding Partner, Deep Law) for a no-BS conversation on the legal landmines, ethical dilemmas, and massive opportunities AI is creating across startups, scaleups, and enterprise.

We unpacked:
• Why “automating innovation” can easily become “automating liability”
• The IP, contract, and privacy red flags that kill valuation at due diligence
• Why GenAI isn’t exempt from copyright—and what the courts actually look at
• The myth of the AI-free workplace (spoiler: shadow AI is everywhere)
• How to actually mitigate risk using AI as a legal tool (and yes—some lawyers use GPT in court)
• What happens when an AI chatbot misquotes company policy in front of a judge 👀
• The biggest legal edge for founders in 2025 (hint: audit trail = valuation moat)

Whether you’re a tech CEO, in-house counsel, or just trying to stay out of the headlines—this one’s essential.

(00:00) Introduction to the AI CEO Podcast
(02:09) Meet the Expert Guests: ambur Smith and Cameron Powell
(03:30) Legal Dynamics and AI
(08:36) AI in Legal Practice: Tools and Trust
(19:58) Challenges and Responsibilities in AI Adoption
(45:11) Understanding AI in Legal Practice
(46:03) Diverse Perspectives in Law and Technology
(47:54) Use Cases: Successes and Failures
(48:22) Risk Hierarchy and AI Implementation
(50:38) Guardrails and Legal Research Tools
(51:50) AI in Marketing and Real Estate
(53:32) Innovations in Regulated Industries
(55:30) Data Privacy and Ethical Considerations
(57:54) Navigating Legal Risks in AI
(01:13:25) The Future of AI in Legal Representation
(01:20:29) Rapid Fire Questions and Final Thoughts

Liability-as-a-Service – Without legal vetting, your AI product isn’t a SaaS. It’s a ticking time bomb.
Copyright ≠ AI Immunity – If your content was auto-generated, you may not own it—and can’t enforce it.
Red Line Rule – If you didn’t revise the AI’s draft, you may not hold the copyright.
Shadow AI Is Real – Banning AI tools doesn’t stop your team from using them (secretly).
Trust, but Verify – From discovery tools to ChatGPT, the best lawyers use AI—just not blindly.
Generalist Advantage – The most valuable legal minds are those who blend tech, product, and policy fluency.

• Ambur Smith Law – https://ambursmithlaw.com
• Deep Law (Cameron Powell) – [Insert Link]
• Virgent AI (show sponsor) – https://virgent.ai
• Seema Alexander – https://www.linkedin.com/in/seemaalexander

Instagram – https://www.instagram.com/seemaalexander
Newsletter + consulting – https://www.disruptive.ceo/

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Share this episode with someone launching an AI product today—before the lawsuits hit tomorrow.