Latent Space: The AI Engineer Podcast

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

Release Date: December 12, 2025

Overview:

In this episode, the Latent Space podcast dives deep into the intersection of AI, enterprise sales, and startups with Joubin Mirzadegan—a veteran sales leader, partner at Kleiner Perkins, and now founder of Roadrunner, KP’s latest AI incubation. The discussion unpacks how foundational models, leadership, and distribution define the new wave of enterprise AI startups. Joubin reflects on his own career pivots, the grind of starting a podcast and company, his learnings from Glean and Windsurf, and why a product like Roadrunner could be the next big disruptor for the complicated world of enterprise quoting (CPQ). The conversation weaves in firsthand advice on sales hiring, founder grit, the creator economy, and high-performance personal routines—making it essential listening for AI engineers, founders, and go-to-market strategists alike.

Main Topics & Discussion Points

1. The Pain and Complexity of Enterprise CPQ Software

[00:00, 39:01, 41:15]

• Joubin shares horror stories of using legacy CPQ (Configure, Price, Quote) systems like Salesforce, highlighting immense user friction:
  • “Like 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.” [00:03]
• Explains how B2B pricing models exploded in complexity—moving from simple per-seat models to a confusing mix of consumption-based, volume, discount tiers, and more SKUs.
• Notes that AI, especially LLMs, are uniquely suited to abstracting away this complexity, similar to their use in legal (Harvey) or code (Windsurf/Cognition) domains.
• Identifies a massive, industry-wide CPQ pain point validated by repeated CIO dinners:
  • “Pain does not grow on trees like that...” [42:56]
• Salesforce’s CPQ is being end-of-lifed; incumbents lack the architecture to address new complexity, leaving a two-year window for disruption.

2. From Sales Leader to Venture Podcaster to Founder

[05:46, 08:22, 09:46, 13:33]

• Joubin’s unique career path: from successful startup sales (acquired by Palo Alto Networks), to KP VC, to podcasting as a way to network with CROs when he lacked a personal “coaching tree”.
• Genesis of the “Grit” podcast at KP:
  • “I needed an excuse to get to know people that I do not know today. And so that was the genesis was like, how do I figure out a creative way to get to know these chief Revenue officers and help them tell their story?” [08:05]
• KP was initially skeptical about a VC-led podcast but greenlit it after hearing a pilot episode.
• Joubin’s podcasting philosophy: deep guest prep, raw, unrehearsed conversations, and making guests comfortable to surface true insight—never sending guests questions in advance:
  • “If you give the guest the questions, well, all of a sudden it's like a rehearsed set of conversations, which is not how real life goes.” [14:00]

3. Podcasting as a Platform & Media Dynamics

[11:46, 12:37, 13:33]

• Deliberation between audio-first vs. video-first formats.
  • Joubin prefers less production: “...the minute that you have cameras everywhere with lights all over the place illuminating something, it feels more noticeable to the guest.”
• The “creator trick” of recording as soon as guest sits down, avoiding stage persona:
  • “The minute that somebody says, ‘are you ready? Go.’ You build this like idealized version of yourself that you want to project to the world, which is like not real.” [13:33]

4. The Glean Playbook: Enterprise AI Under the Hood

[16:05, 18:46, 19:41, 21:14]

• Early Glean faced skepticism—enterprise search was seen as a “dead” category plagued by failed promises.
• Secret to breakthrough: technical excellence plus a design partner strategy (Rubrik acted as early customer and development partner).
• Achieving credibility:
  • “At least you can show, hey, this is like working in production for somebody.” [19:28]
• For complex, sensitive AI deployments (enterprise search, code), deep customer partnership and hands-on technical support are required due to both product and “sand-under-your-feet” tech shifts.

5. Sales, Leadership, and Go-To-Market for AI Startups

[22:33, 25:47, 27:02, 29:02, 30:09, 31:28, 32:20, 33:45, 34:05, 34:52, 36:07, 37:12]

• KP’s differentiator: active help for technical founders in sales, demand gen, and hiring—not just money.

• Anatomy of Windsurf’s hypergrowth:

  • “0 to 100 million ARR in seven months... It was the most torrential growth I think I've ever seen in a KP company.” [26:22]
  • Windsurf succeeded because of: equal focus on product and distribution, a hot technical market (AI coding), and assembling elite sales talent quickly.

• How to hire your sales team (and anti-patterns):

  • Don't just hire “logo’d” people from big names (Databricks/Snowflake) at mature stage; seek out those who succeeded with the #3 product in a market or have real startup scrappiness.
  • First-time executive talent often outperforms “seasoned” veterans:
    • “38 out of 40 of those roles… report to the CEO for the first time in their career.” [32:20]
  • Sales leaders must be more technical than ever in AI; must deeply understand product and customer context—not just run a playbook.
  • Right fit: hire for the company stage, not just resume pedigree. Early employees must be “artists”, creators, not playbook runners.

• Memorable Quote:

  • “In the early days, like it is, it's creative ways of getting something done. It's creative ways of getting something done. And it just looks more like art than it does in science.” [37:15]

6. Roadrunner: The Thesis, Team, and Approach

[39:01, 41:39, 44:18, 47:49, 49:19, 50:03, 52:28, 53:24, 54:07, 56:05]

• Problem: Modern B2B companies face extreme quoting and pricing complexity that legacy CPQ tools (Salesforce, etc.) can’t handle—especially consumption-based, AI-driven pricing.
• Market validation: repeated, intense, consistent pain from CROs and CIOs at major tech companies.
• Incumbents are architecturally frozen:
  • “In order for an incumbent to go do what like a Harvey is doing, you have to literally rebuild that company from the ground up.” [44:18]
• Roadrunner’s edge: unique founder-market fit—Joubin’s deep relationships, and technical cofounders with “unfair distribution” and Mars rover-level engineering experience.
• Development approach: four hairy “design partners” co-developing the product in tight feedback loops, with a data model engineered for infinite flexibility.
  • “What you want are the hairiest design partners that have every SKU, hardware, software, SaaS, consumption. Like you want the mess to throw that at your data model to make sure that nothing tips it over.” [51:24]
• Long term AI vision: true LLM-powered “deal desk” intelligence that can recommend deal structure, produce quotes, and automate away AE’s administrative overhead.

7. Grit, High Performance, and Personal Practices

[59:50, 61:12, 62:20, 66:32]

• Joubin’s routine: “I work out every day no matter what… Salad for lunch every day. I’ve just found that if I can just do the same things over and over again, my life is just easier. I don’t have to think about it.” [59:50]
• Principle: high performance means systematizing habits to remove cognitive load and maintain peak productivity.
• Grit, by Angela Duckworth’s definition: “Passion plus perseverance over a sustained period of time.” [66:49]
• Joubin’s spin: Focus on what you deeply care about—makes enduring the grind feel effortless, be it podcasting or company-building.

Notable Quotes & Key Moments

• “If Priscilla Chan gets half of what she wants to do done, she will have more impact on humanity than Mark Zuckerberg. Facebook will just be a funding mechanism for the greatest bioresearch work done in human history.” — Fresno [01:33]
• “You kind of are making a pre commitment that you're going to tune out the noise, because otherwise you start overreacting to what any single person thinks about any given episode.” — Sam [09:59]
• “The bar for how technical you are is going up. Salespeople gotta be technical. Much more than they used to be.” — Sam [34:05]
• “What I love about [Glean] is now it's become one of the obviously great AI companies that's like in the heart of the hurricane. Back then it was like extremely unobvious. Extremely unobvious.” — Sam [18:28]
• “So AI is about to make this problem [CPQ] way worse.” — Sam [41:39]
• “The dream where LLMs will be a superstar in this company is like, if you're one of our customers and all quotes go through Roadrunner, basically you can imagine a world where it just recommends just do this deal.” — Sam [56:05]
• “The prize [in startups] is just more pie.” — Sam, on the endless grind [62:20]
• “My favorite definition of sales is an ability to transfer enthusiasm from one person to another.” — Sam [65:33]
• “If I really care, then I'll just do it for longer than anybody else and just out sustain you. But I think it's all because I really care.” — Sam, on true grit [67:18]

Timestamps for Key Segments

| Timestamp | Segment | |-----------|---------| | 00:00–03:00 | Horror stories of legacy sales/CPQ software | | 05:46–09:34 | KP podcast origin story & the value of earnest founder conversations | | 13:33–15:07 | Raw conversation “tricks”, free flow podcasting prep methodology | | 16:05–19:41 | Glean’s breakthrough, design partner model for enterprise AI | | 22:33–26:22 | KP’s value add: go-to-market services for technical founders | | 26:22–29:21 | Windsurf’s hypergrowth: product & distribution DNA | | 30:09–33:45 | Anti-patterns & best practices for hiring sales teams in AI startups | | 34:05–37:30 | Technical bar for AI sales, stage-appropriate hiring | | 39:01–44:18 | Roadrunner: the enterprise quoting problem, market timing, and technical opportunity | | 47:49–53:24 | Roadrunner’s team, design partner approach, data model challenges | | 54:07–56:05 | Why solve big problems before bold vision, and the real value of AI in CPQ | | 59:50–62:20 | Daily routines, high performance without cognitive overhead | | 66:32–68:11 | What is grit? Passion plus perseverance and caring deeply |

Conclusion

This episode offers a masterclass in modern AI startup strategy, the reality of scaling enterprise go-to-market, and the personal grit required to sustain at the highest level. Joubin Mirzadegan’s journey from sales leader to podcast host to founder culminates in Roadrunner—a timely response to a deep, validated pain point in the enterprise, leveraging both foundational models and an “earned right” distribution network. The chat is an unfiltered look behind the curtain of both podcasting and company-building, blending AI insight, tactical advice, and authentic personal reflection that’s sure to resonate far beyond the KP portfolio.

Want more? Full notes and resources at latent.space