Leap Academy with Ilana Golan
OpenAI's Former Head of GTM: What Leaders Get Wrong About AI & What’s Coming Next | Zack Kass | E142
27 Jan 2026
Chapter 1: What is the main topic discussed in this episode?
Jobs changing doesn't have an economic consequence the way it does an emotional one. And that is actually the crisis we are tracking towards.
Chapter 2: What led Zack Kass to become Head of Go-To-Market at OpenAI?
The greatest sacrifice that our generation will pay vis-a-vis AI is extricating who we are from what we do, because what we do will change so much and so frequently.
Zach Kass is the former head of go-to-market at OpenAI, the company that gave us Chatupiti.
Chapter 3: How has AI evolved to impact modern industries?
And for years, he was the bridge between the world's most powerful AI and the businesses trying to understand it.
For a lot of people right now, the scary part is that a new technology will show up and they'll be like, wait, maybe I should do that job. I've arrived now at a place where I firmly believe we are going to house people, we are going to feed people, we are going to educate people. And the hardest part is going to be figuring out why are we here?
Chapter 4: What was the breakthrough that led to ChatGPT's popularity?
And now the question is, how do you constantly reinvent yourself? The answer is probably... Welcome to the Leap Academy with Ilana Golan's show. I'm so glad you're here. In the Leap Academy podcast, I get to speak to the biggest leaders of our time about their career, how they got where they are today, the challenges, the failures, and countless lessons. So lean in.
This episode is going to be amazing. I'm on a mission to help millions reinvent their career and leap into their full potential. land their dream roles, fast track to leadership, jump to entrepreneurship, or build portfolio careers. This is what we do in our Leap Academy programs for individuals and teams. And with this podcast, we can give this career blueprint for free to tens of millions.
So please help my mission by sharing this with every single person you know, because this show has the power to change countless of lives. Deal? Okay, so let's dive in.
Chapter 5: What misconceptions do leaders have about AI?
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Today, we're talking to a man who didn't just witness the biggest technology shift of our lifetime. He actually helped orchestrate it. Zach Kass is the former head of go-to-market strategy in OpenAI, the company that gave us ChatGPT. And for years, he was the bridge between the world's most powerful AI and the businesses trying to understand it.
But then he made a massive leap of his own and he walked away from this rocket ship, to become a futurist and one of the world's leading voices in AI innovation.
Chapter 6: How can individuals adapt in a rapidly changing job market?
And we're going to discuss why he left the hottest job in the tech, why he believed the future is bright with AI, not necessarily scary, but how you can prepare for this era of change. So I can't wait. Let's dive in. Zach, welcome to the Leap Academy show.
Thanks so much for having me, Alana.
Oh, it's going to be so, so fun.
Chapter 7: What lessons can we learn from top innovators in AI?
I'm really excited about this. I will touch your career just for a second, but we're going to dive right into all the AI stuff because I think it's fascinating. But how do you even get to open AI, right? That's not easy on its own.
Chapter 8: What does the future of work look like in the age of AI?
And you've had various roles like figure eight and little, like, can you talk to us a little bit of like, how did you even get to open AI?
I grew up in Santa Barbara, where I am now. And I was not a very good student. I played volleyball in high school and then went to Berkeley. Got in basically because of volleyball and ended up studying history and then added computer science. And sort of as I grew up, figured out that school mattered as like a means to get to the next level. And spent a bunch of time...
in college reinforcing what I had grown up knowing, which is that the world was a great place. And then I found evidence to defend that position. And that's important because it sets the stage for the rest of my career. I graduated Berkeley and I tried to make a career of volleyball, couldn't do that.
went and got a job at the only company that would hire me at the time, which is a company called CrowdFlower, which became figure eight and was the early data labeling company. We were the first company to build human labeled data at machine scale for the purposes of building these better models. That gave me this incredible view into early machine learning.
And from there, I graduated to a company called Lilt, which was building neural nets for the purposes of machine translation, neural networks. And then from there, I got to go to OpenAI and was one of the early employees, 90th employee and helped build the company's sales solutions and partnerships teams.
How did you get to open AI? Was it just like a resume? Did somebody bring you in? Walk me through. How do you even get out of the people's pocket? It wasn't as cool yet, I think.
Well, it was cool to the right people. I mean, it depends on how you define cool and who defines it. It's true. Most people did not know about it. And most people probably at the time called it a cult. I was one of the only people in the world that had sold modern AI. And I'd been selling it for a while. So I knew how it worked. I knew what it did.
For people who don't know, maybe explain to them what is modern AI. I think when ChatGPT came up, it became like wildfire, but there was AI way before that because I came in the tech world and we were talking about AI way before what you're probably mentioning. So maybe dumb it down for people who have no clue what you're talking about.
We've been talking about thinking machines since about 1900. And we've been talking about AI, the term artificial intelligence, since 1954. And these concepts have been pretty theoretical. We didn't really know what it would look like. We just knew that we would eventually or thought we could eventually build machines that were smarter than humans.
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