Salesforce's John Somorjai has spent more than 20 years doing deals for Marc Benioff, from Slack to six rounds of Anthropic, and runs a venture arm that has backed more than 750 companies. His playbook is finding great technology that's starved for distribution and plugging it into 15,000 sales reps. Salesforce piloted Fin on its own help site, where it went live in 14 days and now handles over 40% of the traffic, resolving 65% without a human. John joins a16z's Alex Immerman to discuss why Slack revenue is up almost 3x since the acquisition, how strong revenue can hide the churn that kills deals, the pen test that got into a CEO's laptop, and why robotics is where he's most excited to invest. 0:58 How Marc Benioff spots what to buy 3:48 The 3 tests for every acquisition 5:17 Salesforce's model as AI cuts seats 8:23 Fin resolves 65% with no human 10:32 The power of 15,000 sales reps 14:22 Founders who became product chiefs 17:34 Build vs buy when code is cheap 20:27 Why Salesforce bought Fin 22:58 Why Slack is perfect for AI agents 28:19 Salesforce Ventures' robotics bets 35:46 Why he's wary of new CRM startups 37:53 Why $10B+ startups have few buyers 39:32 Why he backed Anthropic six times 41:50 Red flags that kill acquisitions 44:27 The pen test that sank a deal 46:01 Growing up with a scientist father YouTube: https://youtu.be/y4BdOtm40SA @jsomorjai @salesforce @aleximm