Lessons from 1,000 Mistakes: Kevin Gaither on Scaling Startups & Sales Teams

In this episode of the Biz to Biz Podcast, we’re joined by Kevin Gaither — a seasoned sales leader with over 25 years of experience building, scaling, and fixing sales teams at high-growth startups. With eight startups under his belt, three successful liquidity events, and multiple companies reaching the Inc. 500 and Deloitte Fast 500 lists, Kevin has seen it all — and made more than a few mistakes along the way. Kevin shares the raw, unfiltered lessons he’s learned from decades in the trenches, leading teams of 30 to over 500 salespeople. From recruiting and training to leadership and strategy, his insights are hard-earned and battle-tested. No fluff, just real stories, real takeaways, and real talk about what not to do when growing a business. Whether you're a founder, sales leader, or aspiring entrepreneur, this episode is packed with actionable advice to help you avoid common pitfalls and accelerate your growth. 📈 Experience over opinions. 🎙️ Tune in and learn how to turn mistakes into momentum. 💼 Connect with Kevin: LinkedIn Don't miss this candid and insightful conversation!