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00:00 Kyle's Journey: From Dropbox's Third Sales Hire to Figma's Sales Leader 06:00 When Should Founders Hire Their First Head of Sales? 12:00 The Hardest Part of Founder-Led Sales Transition 18:00 PLG to Enterprise: Why You Might Want the Top-Down Seller 24:00 Building Dropbox Austin: 150 Hires in Under 2 Years 30:00 How Kyle Spotted Figma Before Anyone Else (The 3 Trends) 36:00 Scaling Figma from $2M to $950M ARR 42:00 "Stay Low at the Highs, High at the Lows" - Surviving the Roller Coaster 48:00 Why Founders Pitch Too Early (The Discovery Trap) 53:00 What Kyle Would Tell His Younger Self Episode Description: Kyle Parrish was the third sales hire at Dropbox and the founding sales leader at Figma, where he scaled the business from $2M to $950M in ARR over six and a half years through their IPO. Before Figma, Kyle opened Dropbox's Austin office and hired 150 people in under two years. He's now advising and investing in top AI-native startups. Kyle is one of the most thoughtful go-to-market leaders in the game - his frameworks on PLG-to-enterprise, founder-led sales, and building high-performing teams are pure gold. Also, shout out to our awesome sponsor for this episode, Kondo. Think of it like Superhuman for LinkedIn messages - if you're terminally on LinkedIn like I am and your inbox is becoming unwieldy, give it a try for the first month free using this link (http://trykondo.com/gtm) - it saves me over an hour a day. Discussed in this episode: When founders should hire their first head of sales vs. individual reps Why PLG companies should consider hiring top-down enterprise sellers (not "PLG sellers") The three trends Kyle spotted that led him to Figma before anyone else How to transition from founder-led sales without losing what made it work Opening Dropbox Austin: hiring 150 people in under 2 years and building the GTM hub "Stay low at the highs, high at the lows" - how to survive the startup roller coaster Why founders fall into the trap of pitching too early and skipping real discovery The evangelical early sale: customers are buying the founder and the dream, not the product Building your network like a bonsai tree - intentional cultivation over years What Kyle would tell his younger self Guest Link: LinkedIn - / kparrish8 Twitter - https://x.com/KyleHParrish About The Vibescaling Podcast: The Vibescaling podcast interviews GTM leaders and investors at top AI startups and early-stage companies. Every week, host Chris Balestras, partner @ Vibescaling (an advisory, recruiting, investing, & media firm for seed through series C AI-natives) sits down with GTM operators from the fastest-growing AI natives and SaaS companies to break down what's actually working in go-to-market today. No fluff, no theory - just honest, tactical insights from people in the trenches building the next generation of AI breakouts. About Vibescaling: Vibescaling is an advisory, recruiting, investing, & media firm for seed through series C AI-natives & fast-growing SaaS startups. Where to Find Vibescaling: LinkedIn Company Page - / vibescaling YouTube - / @vibescaling Newsletter - https://www.vibescaling.blog/ Website - https://www.vibescaling.ai/