Uncapped #54 | Sam Blond from Monaco

Sam Blond is the co-founder and CEO of Monaco, an AI-native revenue automation platform built to replace the CRM as the system of record for sales. Before Monaco, Sam was a Partner at Founders Fund and before that one of the most accomplished go-to-market executives in the tech industry, having served as VP of Sales at EchoSign (acquired by Adobe), VP of Sales at Zenefits, and Chief Revenue Officer at Brex. We discussed Sam's entire sales journey from EchoSign through Zenefits, Brex, and Founders Fund, and what he learned at each stop. Sam shared his framework for creating a demand-rich environment and why most founders misdiagnose their revenue problems as conversion issues when they're really pipeline issues. We got into why Sam believes Salesforce faces a classic innovator's dilemma and why the next category leader in sales will be a platform architected with AI in mind from day one. We also covered Monaco's go-to-market playbook, how Sam thinks about pricing when you're selling labor disruption rather than software, and his two pieces of advice for founders who are just starting to sell. Timestamps: (0:00) Intro (1:26) Sam's sales journey (3:11) Echo Sign takeaways (5:28) Building Zenefits GTM (7:02) Parker's 0 to $10M thought exercise (9:51) Creating a demand-rich environment (14:20) People, brand, and revenue ops (21:19) Why Sam went to Founders Fund (28:00) Why Monaco, why now (29:40) The Salesforce innovator's dilemma (31:40) Why Monaco chose to be the system of record (34:30) Disrupting labor (41:10) Pricing in an AI-native business (44:28) The Monaco GTM playbook (50:06) The $60,000 plane experiment (54:21) Creative campaigns vs. paid advertising (1:00:06) What Monaco actually does (1:03:13) Advice for founders just starting to sell (1:07:58) Abundant pipeline and the right to say no