AI to AE's: Grit, Glean, and Kleiner Perkins' next Enterprise AI hit — Joubin Mirzadegan, Roadrunner
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What was the inspiration behind the Zuck interview and the podcast’s opening?
During my sales career, probably the number one thing that used to break my back was that the underlying software. With like uh Salesforce CPQ and others, just to like create a quote, get it approved, is horrific. Like you think if you think you've seen bad software, you haven't until you've seen a 30-second loading screen to get from one page to another when you're trying to close a deal with like two days left in a quarter. This is just like standard across the industry. This I worked at every job that I was ever at. I used to get yelled at because I would like be asked. Asking people to like turn something within a day or two because I needed to get a quote out the door. I was like, oh my god. I actually think you can abstract away a bunch of the complexity with these LLMs.
And it's you know an unstructured and structured text that you can reason with and do stuff with, right? Like that's why coding is such a great use case. That's why Harvey is such a great use case, because you have like all this case law. And then you can point the LLM at it and you can reason with it. Then you build a bunch of enterprise features and functionality and workflows on top of that. This is a very similar problem in nature. And so that was like the light bulb moment of like, okay, I think we can actually build something better. I feel good. I feel comfortable in this seat. How's my levels? What's that? How's my levels? Yeah, you're good. All right. Um I gotta ask you. How is the how is the Zuck interview?
Yeah, it's very interesting. Are we recording? Yeah, yeah, I just wrote. Yeah, yeah. Um I think They kind of obviously had an agenda coming in, which was basically to raise the profile of CZI and Priscilla Chan, with Zuck being supporting c character, right? And I think they accomplished their mission. Uh, because you know, the my my quick hot take in in a single sentence is if Priscilla Chan gets half of what she wants to to do done, she will have more impact on humanity than Mark Zuckerberg. Right. The Facebook will just be a funding mechanism for the greatest bio research work done in human history.
Well Were you nervous?
You must have been nervous. Uh I I wasn't nervous because of the sheer amount of prep that the CZI people put into us. Which which like honestly like low key, to understand what it's like with the executive staff of a hundred billionaire. I've never dealt with someone like that. Yeah. They are so good. They they like they prepped us so well so so that like I felt like I knew exactly You
mean Zuck's team isn't randomly letting people walk in
off
the
street and just ask whatever without any pre based pre-basing knowledge. I feel had to like interview three times to get even in that room. So yeah, it was it was very it was very fascinating. Uh we were very honored to be picked by them because we're not a biofocused podcast. No. But the whole point was to reach out to engineers. And while there there we're on a stronger footing.
Yeah. That's awesome, man. I mean it feels like a breakthrough, doesn't it? You've had some studs on.
Yeah, uh we just had Faith Fa Lee today. Uh the today just re yeah, just just released. Well labs. Uh no, and they we just released it. Oh you did? That was a couple of weeks ago. Who else have you done? There's a bunch, Greg Brockman. We've done
some amazing people.
Is it surreal? Yeah, it's it's surreal for me who started out as just like an independent creator. Let's see where this goes. To now we're legitimate j legitimately in that tier of podcasts that gets invited to everything. So that is very surreal.
Yeah.
It's pretty exciting. Who would have thought, you know? I mean, I think like for you, I've been following your progress for a while. I don't think when you were still like a CRO podcast, I don't think I I was caught caught in audio yet, but I think like anyone following top founders who really wants to get real stories, they v eventually find their way to you and you get really good stuff. So congrats. I appreciate
that. I um I think the the transition from the CRO to the founder, whatever, it happened like what episode 70 or 80 when I was like, because it was only CROs for a while.
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Chapters
8 chapters
1
What was the inspiration behind the Zuck interview and the podcast’s opening?
0:00–8:25
2
How did Joubin create the CRO‑only “Grit” podcast as a hiring wedge?
8:25–16:01
3
What lessons did Joubin learn from building the Grit podcast’s authentic conversations?
16:01–25:53
4
How did the partnership with Arvind at Glean shape the product and go‑to‑market strategy?
25:53–34:05
5
What made Windsurf’s sales machine a benchmark for “Google‑class product + Salesforce‑class distribution”?
34:05–42:56
6
What anti‑patterns should founders avoid when hiring early sales leaders?
42:56–51:50
7
Why is the CPQ/quoting problem a critical pain point for modern revenue teams?
51:50–1:01:02
8
How does Roadrunner rebuild the CPQ data model with AI to automate deal recommendation?
1:01:02–1:09:32
Speakers
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