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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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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.
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