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Grit · 3 min · Mar 9, 2026

Sierra pairs enterprise experience with AI-native graduates

Sierra hires experienced people for large-company credibility and trains new graduates for agent roles. The mix helped it win customers at the top end of the market early.

Bret Taylor

Bret Taylor is co-founder of Sierra.

Co-founded and leads Sierra, an enterprise AI agent company; chairs OpenAI's board and co-created Google Maps.

  • Joubin Mirzadegan, Host · Partner, Kleiner Perkins

    Took Palo Alto Networks' cloud business from $2M to $50M+ ARR in a year.

About this segment

Sierra hires experienced people for large-company credibility and trains new graduates for agent roles. The mix helped it win customers at the top end of the market early.

From “How Sierra Is Pulling Ahead in the AI Race | Co-founder Bret Taylor”, Mar 9, 2026. Watch the full episode

“We couple it though with a lot of very young people too. So we have this program called the APX program”
Bret Taylorat 5:48 · Grit5:48

Takeaways

  1. Fortune 100 customers require knowledge of legacy systems and regulation.
  2. The APX program trains graduates as agent product managers and engineers.
  3. More than a quarter of customers have over $10 billion in revenue.

In this episode

Full episode
  1. 11:55Leaders have to test internal stories against customers4:38
  2. 22:35Applied AI will rely on a portfolio of specialized models4:16
  3. 32:44AI's impact depends on task complexity and real-world bottlenecks5:51
  4. 52:40Paid proofs of concept filter out AI tourism5:38
  5. 48:13Sierra chose financing partners over the highest valuation3:05
  6. 38:52AI gains will fuel competition as well as efficiency5:45
  7. 4:05Sierra pairs enterprise experience with AI-native graduates2:59

  8. 17:27AI is expanding contact-center demand while capital delays consolidation4:30Up next

Transcript

Transcribed by machine (Whisper) from the episode’s audio, so a word may be off here and there.

  1. 4:10

    but one of my observations actually just looking at the Sierra employee base is seemingly from the beginning, you hired both aggressively and senior. Again, I don't know. I'm just reading back to you what I have observed from looking at the leadership team. You had executives that I would say we're pretty senior kind of from the jump and you've staffed the team accordingly basically since the beginning and you know like my first of all do you think that's true before i continue i'll start with the reason why and then end with basically agreeing with you uh-huh we started the company with the thesis that a lot of the impact we can have on the economy and the world is through some of the largest companies in the world.

  2. 4:58

    So we said, hey, the Fortune 100 is, you know, the cohort of, that's our ideal customer profile. And to serve, you know, a company like Cigna Healthcare or, you know, DirecTV, you have to be able to actually go into those companies and know what you're talking about, understand, you know, what a mainframe is, and understand that not every company uses like next generation software as a service, but there's legacy systems.

  3. 5:28

    You have to understand regulations. And so part of that is when we built the company, we built it around really being able to serve these businesses. And so as a consequence, we wanted in parts of our business, we want to make sure we had people with some experience just because it's hard to go into, you know, we serve a pretty high percentage of the Fortune 20 at this point. And to do so, you have to be able to have credibility in that room. We couple it though with a lot of very young people too. So we have this program called the APX program, which is modeled after where I got hired at Google, where we hire new graduates out of engineering degrees and teach them how to be agent product managers or agent engineers. And it's like a rotational program, just like the APM program at Google. So I would say we kind of get both ends of that, where we have people who

  4. 6:16

    to understand the business of enterprise software and understand how to work with the most complex businesses in the world and the most talented young people we can find who are AI native, I guess you could say. And we think that's our kind of sweet spot in the market. But yes, we have tired more experienced people. We are planning for success to some degree. And actually, I think it's born out in the numbers, not just the ARR numbers, but over a quarter of our customers have over 10 billion in revenue, which for a company that's been in the market for two years is very unusual you tend to usually start with smaller customers and move out from there and we've started kind of at the top end of the market which was very intentional yeah the you just had to be right right because if you have