From CNN to Google to Founder

What we talked about.

Sunny Ray sits down with Anisha, founder and CEO of Checkout.ai, a data intelligence company building personalized and eventually agentic shopping experiences for ecommerce brands. Anisha traces her path from a childhood in Johns Creek, Georgia, teaching herself to code at eleven, to becoming a fluent Punjabi and Hindi speaking journalist at CNN International covering conflict in South Asia. She describes founding her first startup, Udebate, earning a masters in computer science at Georgia Tech, then working at Google on security and privacy policy, moving into private capital at Ares Management, and studying at Stanford GSB. She also shares how theater and improv shaped how she manages people. The conversation dives deep into Checkout.ai's product, a fifteen minute install chatbot that gives ecommerce brands customer analytics and personalization, its rollout on Shopify and Shop, its partnership model with Google, and her vision for a future where AI agents autonomously shop on behalf of consumers. She closes by reflecting on resilience as a female founder in a male dominated venture landscape.

From CNN war correspondent to Google policy lead to building the agents that may soon do your shopping for you.

The questions, and the answers.

What is Checkout.ai and what are you building right now?

Checkout.ai is my brainchild, born from my obsession with personalized consumer buying behavior. Big retailers sell generic products, but I wanted brands to check customers out in a way that's tailored to them while giving brands real customer intelligence in return. So we built an AI enabled shopping agent that personalizes the experience for the consumer and hands brands better customer insights.

Before AI, before Google, where did you grow up and what were you obsessed with as a kid?

I grew up in a family of Punjabi immigrants in Johns Creek, Georgia, outside Atlanta, in a predominantly white community at the time. My parents worked hard, and I think that's where I get my grit and resilience. My dad, an engineer, gave me my first laptop, and by eleven I was taking it apart, and by twelve I'd learned to code at a girls coding camp.

Your first job out of college was journalism at CNN International. What pulled you toward the newsroom first?

There wasn't much computer science available at my schools growing up, so I didn't pursue that path directly. I'm fluent in Hindi, Punjabi and English, and CNN didn't have Punjabi speakers on their desk, so I got an internship as a translator. I quickly became part of the international assignment team covering stories out of Afghanistan, Pakistan and Iran.

What made you trade the press badge for big tech, jumping into Salesforce and then Google?

I knew journalism had a ceiling for me, and I'd already won an Emmy and covered one of the biggest stories of the century while still young. After journalism I started a debating platform called Udebate, essentially trying to be Reddit before Reddit. After that failed to scale, I got into Georgia Tech for a masters in computer science, which changed my career trajectory.

At Google you ran security policy programs, herding lawyers, engineers and compliance teams into agreement. What did that teach you about how massive systems get things done?

It combined everything from my startup and journalism experience, since journalism also means working with many stakeholders under high pressure. At Google I worked with some of the brightest people in the business and built relationships with lawyers and senior engineering managers. I learned how to execute in high pressure, highly technical environments at scale and efficiency, first in security policy, then privacy with 600 engineers.

You also spent time at Ares Management. What did sitting near the capital side of the table teach you that operators usually miss?

Being on the capital side actually pushed me toward starting my own company. I'm inherently an engineer who likes to build and scale, but at a firm like Ares there's no building happening, it's mostly purchasing. The itch to build wasn't being fulfilled there, so one day I just decided I wasn't designed to be an operator and started my own company.

You've performed in theater and written about going from tech to the stage. What does live performance teach you that the boardroom never could?

Theater and stage work taught me more about managing human capital than any corporate learning could. Whether you're handling engineers, lawyers or actors, you have to quickly identify personality types and what people need to bring them together toward a mission. Theater is a different kind of grit, it's human grit, and it sharpened my ability to think fast on my feet.

Roughly seven in ten online shopping carts get abandoned. How does putting an agent in the store change that math?

We've seen a 20 percent increase in sales when a customer engages with our agent. If they go through the full discovery process with the agent, we see almost 100 percent conversion, because the customer develops buyer trust, feeling the brand has done its research and the product genuinely fits their unique needs.