In this episode of The Digital Executive, host Brian Thomas speaks with Ruby Kolesky, CEO of Joyous, an AI-powered feedback platform transforming how organizations listen, learn, and act. From her early days pursuing stand-up comedy to leading one of New Zealand’s most innovative tech companies, Ruby shares how empathy, humor, and human insight guide her approach to building smarter, more human-centered AI. She dives into why traditional surveys fail, how Joyous replaces static feedback loops with dynamic one-on-one conversations at scale, and why she believes human connection—not automation—will become the ultimate premium. Ruby also discusses the importance of democratizing voice in large enterprises and how real-time, actionable insights from the frontline can drive both performance and purpose. If you liked what you heard today, please leave us a review - Apple or Spotify.  See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.