Anthropic’s first technical PM on token maxing, the jagged edge, and living in the future | Dianne Penn

**Dianne Penn** (0:00)
In 2023, when I started, nobody said Anthropic and Claude and coding in the same sentence.

**Lenny Rachitsky** (0:06)
I want to go back to the beginning of Anthropic. I remember feeling, man, these guys have no chance. OpenAI is so far ahead.

**Dianne Penn** (0:14)
By the time I saw people were starting to use these models, not just for code autocomplete, but actually writing long-form code. It's not an opportunity for us to train Opus 3 to be better at. That was the inflection.

**Lenny Rachitsky** (0:26)
I always think about Opus 4-5 a year later, during winter break when everyone was home able to code.

**Dianne Penn** (0:31)
What was magical about Opus 4-5 is we also now not just had a model, but a vehicle, a great product experience like Claude Code. Opus 4-5 wouldn't have had that moment without a product like Claude Code, and Claude Code wouldn't have had that type of adoption accelerated without Opus 4-5.

**Lenny Rachitsky** (0:50)
I want to talk about how the product role is changing.

**Dianne Penn** (0:53)
For my team, the way to drive user value is to figure out the right user feedback, the evals, we actually have a saying on the team of evals are the new PRDs.

**Lenny Rachitsky** (1:02)
Something Gary Tan's been talking about, if you are willing to spend $100,000 a year right now in tokens, you are living the way somebody in 2020 is going to live.

**Dianne Penn** (1:10)
You have to sweat the tokens as much as you sweat the pixels. You have to be using the models to come up with good and great and better ideas, and there's no substitute for that.

**Lenny Rachitsky** (1:20)
People need to be more ambitious with AI tools these days because they're just capable of so much.

**Dianne Penn** (1:25)
One thing I ask the team is, let's say Claude 8 comes around, what changes in what users do? What does that mean for how you're building today?

**Lenny Rachitsky** (1:36)
Today, my guest is Dianne Penn, Head of Product for the AI Research and Labs Teams at Anthropic. She joined Anthropic as the first technical product manager over three years ago, which is a lifetime in AI time. When the product team was just five engineers, she's helped ship every model at Anthropic from Claude 2 through Fable. She's also helped incubate and launch Claude Code, MCP, Skills, Claude Design, and also core capabilities like computer use, tool use, and reasoning. It is always such a treat and so mind expanding to get to talk to someone who's at the very center of AI and product management. It's hard to imagine someone who has seen more of where things are going than the Head of Product for Anthropic's Research and Labs Teams. Before we get into it, don't forget to check out lennysproductpass.com for a year free of hottest and most beautifully crafted AI products in the world, available exclusively to Lenny's newsletter subscribers.
With that, I bring you Dianne Penn.
Dianne, thank you so much for being here. Welcome to the podcast.

**Dianne Penn** (2:40)
Thank you, Lenny. It's so nice to see you again.

**Lenny Rachitsky** (2:43)
I want to go back to the beginning of Anthropic, the early days. I remember when Anthropic first launched, I don't know, the first model when it launched, years ago, three years ago, something like that. It was. Three years. I remember just feeling that, man, these guys have no chance. OpenAI is so far ahead.
What are they thinking? How is this possible? OpenAI is one, it's too late. Things are very different now. The latest number I saw was Anthropic was making, I don't know, $50 billion in ARR. That's what companies used to go public at. Very successful companies went public at $50 billion in valuation. Anthropic reportedly is making that every single year.
You joined as one of the earliest PMs. There were something like five engineers when you joined. The model hadn't even launched when you joined.
What was it like in those early days of Anthropic? What's something that might surprise people about what it was like at the beginning?

**Dianne Penn** (3:44)
I think a big part of what's made Anthropic today actually has been very much the core of even the early days. I joined in 2023 Like you said, we had five product engineers. There was one engineer for the entirety of our API business, if you believe.
I think a big portion of it was the culture was really strong. I think this is something I emphasize for folks who are interested in the company, really do walk the walk of the mission and the culture and the values.