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AI to AE's: Grit, Glean, and Kleiner Perkins' next Enterprise AI hit — Joubin Mirzadegan, Roadrunner

Overview

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AI to AE's: Grit, Glean, and Kleiner Perkins' next Enterprise AI hit — Joubin Mirzadegan, Roadrunner

Latent Space: The AI Engineer Podcast

2025/12/12
Latent Space: The AI Engineer Podcast

Latent Space: The AI Engineer Podcast

2025/12/12
OverviewShownoteHighlightsTranscriptChaptersPins

Shownote

Glean started as a Kleiner Perkins incubation and is now a $7B, $200m ARR Enterprise AI leader. Now KP has tapped its own podcaster to lead it’s next big swing. From building go-to-market the hard way in startups (and scaling Palo Alto Networks’ public c...

Highlights

In this episode, we explore the evolving landscape of enterprise AI and go-to-market strategy through the lens of Joubin Mirzadegan’s unique journey—from building a CRO-focused podcast as a talent magnet to incubating Roadrunner, an AI-native solution for modern revenue operations. His experience spans startups, scaling cloud businesses, and working closely with technical founders at Kleiner Perkins.
00:00
LLMs can simplify complex sales software like Salesforce
09:03
Producing 100 episodes was a commitment to avoid premature judgment.
13:20
Start recording early and avoid asking if the guest is ready to capture genuine moments.
24:34
Windsurf achieved zero to $100M ARR in seven months with a strong sales machine.
26:21
Combining a good product team like Cognition's with a strong sales team like Windsurf's is a formula for success
38:38
Roadrunner is the hottest KP incubation since Glean.
41:39
The underlying data model of Salesforce CPQ is breaking due to modern permutations.
43:45
Salesforce is ending its CPQ solution but the new product is not ready, creating a two-year window to beat them.
55:12
Roadrunner aims to automate the deal desk and augment AEs using LLMs.
59:36
It's easier to do something 100% of the time than to negotiate with yourself repeatedly.
1:09:10
True learning happens when you teach yourself and build things.

Chapters

Introduction and the Zuck Interview Experience
00:00
The Genesis of the Grit Podcast: Hiring CROs Through Content
03:26
Podcast Philosophy: Creating Authentic Conversations
13:20
Working with Arvind at Glean: The Enterprise Search Breakthrough
15:44
Windsurf's Sales Machine: Google-Class Product Meets Salesforce-Class Distribution
26:20
Hiring Sales Leaders: Anti-Patterns and First Principles
30:28
The CPQ Problem: Why Salesforce and Legacy Tools Are Breaking
39:02
Introducing Roadrunner: Solving Enterprise Pricing with AI
43:40
Building Roadrunner: Team, Design Partners, and Data Model Challenges
49:19
High Performance Philosophy: Working Out Every Day and Reducing Friction
59:35
Defining Grit: Passion Plus Perseverance
1:06:28

Transcript

Joubin Mirzadegan: During my sales career, probably the number one thing that used to break my back was that. The underlying software with like Salesforce, CPQ and others, just to like, create a quote, get it approved, is horrific. Like you think, if you t...