The VC Who Built a Podcast to Hire CROs and Now Fix Pricing for Enterprises — Joubin Mirzadegan
Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
Podcast Summary
This episode features Joubin Mirzadegan, a venture partner at Kleiner Perkins who has spent the last decade obsessing over distribution and go-to-market strategies. From launching the CRO-only podcast "Grit" as a hiring wedge to working with breakout companies like Glean and Windsurf, Joubin shares his journey from sales leadership to venture capital. (02:36) The conversation dives deep into the real mechanics of creating authentic podcast conversations, the challenges of enterprise AI adoption, hiring early sales leaders, and the massive CPQ (Configure Price Quote) problem plaguing modern revenue teams. Most notably, Joubin unveils his new company Roadrunner, a Kleiner Perkins incubation that's rebuilding CPQ and quoting workflows from the ground up using AI-native architecture.
- Main themes: The intersection of media as a business development tool, enterprise AI go-to-market challenges, the breakdown of traditional pricing models, and how AI can solve complex B2B workflow problems
Speakers
Joubin Mirzadegan
Joubin is a venture partner at Kleiner Perkins who built his career in startup sales and go-to-market before scaling Palo Alto Networks' public cloud business. He launched the "Grit" podcast initially focused on CROs as a relationship-building and hiring tool, which has since evolved into interviewing top founders and executives. At KP, he works closely with technical founders on distribution and sales strategy, notably supporting companies like Glean and Windsurf. He's currently incubating Roadrunner, an AI-native solution for enterprise CPQ and pricing workflows.
Key Takeaways
Start Recording Immediately to Capture Authentic Conversations
Joubin never asks "are you ready?" before starting a podcast recording because it makes guests clam up and start projecting an idealized version of themselves. (13:29) He also controls environmental factors like room temperature (keeping it cool), lighting (positioned up rather than down to avoid a spotlight effect), and never provides questions in advance. This approach creates conversations that feel more like real life rather than rehearsed performances. The principle extends beyond podcasting - authentic interactions require removing artificial barriers that make people self-conscious about how they're being perceived.
Enterprise AI Requires Extensive Hand-Holding and Forward Deployment
Working with Glean taught Joubin that selling AI to enterprises is harder now than traditional software because organizations must simultaneously learn how to use LLMs in general AND how to use your specific product on top of that "quicksand." (20:18) This is why many AI companies are doing forward deployed engineer motions, essentially co-developing custom solutions for each organization. The key is having early believers as design partners who will give you unfettered access to iterate and prove the solution works in production before trying to scale to other customers.
Don't Hire Sales Leaders Based on Logo Recognition
The biggest anti-pattern in hiring early sales leaders is looking at fancy company logos on LinkedIn and assuming those people will be effective at your startup. (30:31) Someone who sold at Snowflake with an established brand and inbound leads operates very differently than someone who had to fight tooth and nail selling a number three product in the market. Early stage sales is more art than science - it requires creativity and scrappiness that can't be taught through a playbook. Look for intrinsic motivation, stage-appropriate experience, and people who have succeeded in similar company sizes and market conditions.
Modern Pricing Models Are Breaking Legacy CPQ Systems
Enterprise pricing has evolved from simple seat-based models to complex consumption-based pricing with multiple SKUs, bundles, renewals, and usage tiers. (39:02) Legacy systems like Salesforce CPQ were built 20 years ago for static pricing and can't handle this complexity - creating 30-second loading screens and requiring custom workarounds. This problem will accelerate as AI drives more consumption-based pricing models. The underlying data models need to be rebuilt from scratch to handle infinite permutations of rules, discounts, and SKU combinations without breaking.
Focus on Passion, Not Just Perseverance for True Grit
While grit is commonly understood as "gritting your teeth" through difficult situations, Joubin emphasizes that Angela Duckworth's definition centers on passion plus perseverance. (66:57) The key is putting yourself in positions where you genuinely care about what you're doing - when you care deeply, work feels like play, you can transfer enthusiasm to others, and you'll naturally outlast competitors. This approach is more sustainable than pure grinding because intrinsic motivation creates the energy needed for long-term success rather than relying solely on willpower.
Statistics & Facts
- Kleiner Perkins portfolio companies: 38 out of 40 executive roles across their top 8 companies are people reporting to the CEO for the first time in their career. (33:21) This highlights how hiring for potential and context rather than just experience is more predictive of success.
- Salesforce has 95% market share in CPQ (Configure Price Quote) solutions but has end-of-lifed their current product, creating a two-year window for new entrants. (46:08) This represents a massive market disruption opportunity as enterprises are forced to find alternatives.
- Windsurf achieved zero to $100 million ARR in approximately 7-8 months, which Joubin describes as "the most torrential growth I think I've ever seen in a KP company." (26:17) This demonstrates the potential velocity of well-executed AI product launches in developer tools.
