Ep 28: This Hiring Mistake Costs $250K (Most CEOs Make It) (with Cailean Bailey)

If you’re hiring fast but losing steam, and revenue, this episode is for you. Sarah sits down with Cailean Bailey to unpack why most revenue teams aren’t failing because of talent gaps. They’re failing because of bad systems, reactive hiring, and zero clarity on what success looks like. From headcount churn to founder guilt, Cailean brings a brutally honest take on why your next hire won’t save you, and what to fix instead.In this episode, you’ll learn:Why retention debt is a silent pipeline killerHow broken onboarding breaks your brandWhat “mis-hiring” really costs your growthThe fix: better role clarity, stronger feedback loops, and hiring that actually scalesYour hiring playbook isn’t just slowing you down, it’s bleeding revenue. Let’s fix it.Contact Us:Email: [email protected] Website: www.stringcaninteractive.comGuest Cailean Bailey: https://www.linkedin.com/in/caileanbailey/ Reach out to the hosts on LinkedIn:Sarah Shepard: https://www.linkedin.com/in/sarahshepardcoo/Jay Feitlinger: https://www.linkedin.com/in/jayfeitlinger/