AI to AE's: Grit, Glean, and Kleiner Perkins' next Enterprise AI hit — Joubin Mirzadegan, Roadrunner
Dec 12, 2025 · 1:09:44
Joubin Mirzadegan, a Kleiner Perkins partner who incubated Glean and now leads its next bet, Roadrunner, argues that AI-native CPQ can fix the broken quoting workflows that plague enterprise sales. Starting the CRO-only podcast Grit as a hiring wedge, he built relationships that later helped Glean and Windsurf scale. He explains why technical founders need sales leaders with a chip on their shoulder, not just fancy logos, and why Windsurf succeeded by marrying Google-class product with Salesforce-class distribution, hitting $100M ARR in months. Roadrunner rebuilds CPQ's data model from scratch, co-develops with four hairiest design partners, and aims to use LLMs to recommend deal structures, automating the Slack-channel chaos of deal desk.
