The Hottest Product Manager in Tech Right Now 🔥 OpenAI’s Holly Li Talks About Dots | Office Drama

Chloe Shih (0:00)

How does it feel to be the baddest PM out there right now? You went viral, and you're not even on social media.

Holly Li (0:05)

I went up there and I was like, oh, I got this.

Chloe Shih (0:07)

And then Dottie ghosted you.

Holly Li (0:09)

Yeah.

Chloe Shih (0:09)

And you were like, how's it going? Still checking. Yeah, so you went back to SF. What happened?

Holly Li (0:16)

I flew with a one-way ticket, and I was like, I'm not leaving SF without a job. I had met an amazing team, and convinced them to create a PM role for me.

Chloe Shih (0:24)

You made your own job at someone else's company. If I wanted to become a better presenter, what is one tip you want to give to me?

Holly Li (0:30)

Do not be a loser in your own fantasies. Imagine yourself as a f***ing winner. I'm not your average AI tech bro. I am hyper aware that on Twitter, everything is like, how can I get my AI to automate X, Y, and Z for me?

Chloe Shih (0:43)

I think a lot of creators love doing things manually.

Holly Li (0:46)

I am with you. I want to walk inside the grocery store, and not just have AI order stuff for me.

Chloe Shih (0:50)

I can't get over giving it access to my inbox, text messages, finances, help data. What would you say about Dots to more privacy conscious users?

Holly Li (1:00)

Okay, so.

Chloe Shih (1:01)

If you have one tip for people interviewing for an AI product manager role, what tip would that be?

Holly Li (1:05)

Actually use all of the products that are out there. You'd be shocked at how many people just haven't tried the basic workflows and had an opinion about what's working for them. None of us know what the future of AI looks like.

Chloe Shih (1:17)

If a candidate walked in with an iced coffee in their hands.

Holly Li (1:20)

Oh my God, this is making the way around on TikTok.

Chloe Shih (1:33)

Welcome to Office Drama where we define the modern career for Gen Z and Millennials in tech, media and business. I'm your host, Chloe Shih and today in the office, we have perhaps the most talked about product manager in Silicon Valley right now. She just presented at OpenAI's Dev Day and she helped launch DOTS, which is the AI assistant that is all over my social media right now. She went viral for this. I'm so excited to have you here. Please welcome member of product staff, Holly Li.

Holly Li (2:02)

Thank you so much for having me.

Chloe Shih (2:04)

I'm so excited you're here. I know you just got off a plane in San Francisco and you had such a long day. And I think I'm at, am I your last stop of the day?

No, you're not.

Holly Li (2:12)

I'm not. I'm, I'm-

Chloe Shih (2:14)

She has more work to do.

Holly Li (2:16)

I'm keep, yeah, we'll, we'll see what happens after this.

Chloe Shih (2:18)

Okay. Well, my first question to you is, how does it feel to be the baddest PM out there right now?

Holly Li (2:23)

Yeah. I, I just joined Twitter two days ago.

Chloe Shih (2:27)

Yes.

Holly Li (2:28)

In order to meet the moment and combat the haters. So that was kind of new. Yeah.

Chloe Shih (2:34)

Welcome to social media.

Holly Li (2:35)

Yeah. Wow. It's a whirlwind.

Chloe Shih (2:36)

Do you want out yet or you're like, you're okay?

Holly Li (2:39)

I mean, completely honestly, I kind of don't know if I will keep posting or if it's just like a one and done, you know.

Chloe Shih (2:46)

She's a private person.

Holly Li (2:47)

I'm a private person.

Chloe Shih (2:48)

In your personal life, have you ever had a crush on someone who didn't know you existed?

Holly Li (2:54)

Oh, absolutely.

Chloe Shih (2:55)

Like when was the last time that happened to you?

Holly Li (2:57)

Oh gosh. Well, I've been in a relationship for quite many years now. So I feel like the correct answer is to say before that, but you know.

Chloe Shih (3:07)

Yeah. So, you know, I want to ask the drama alamas if you've ever had a crush on someone, whether it's that Coworker in the micro kitchen, or that person at that library studying at the same time as you, or that barista at that coffee shop, because my moment is right now with Holly.

That's you. You're that girl for me. I first fell in love with you when Meche Times Marissa, my friend Meche Times, posted about you at the config 2025 keynote presentation.