AI Coaching: The $20/Month Answer to a $500/Hour Problem

AI coaching has been a promise for years. Aaron Ward, co-founder and CEO of Huckleberry, is the one actually delivering on it — with a voice-based coaching platform you can put in the hands of every employee for $20 a month. In this live conversation from Transform 2026, Work Tech Weekly host Steve Smith and Aaron dig into why privacy is the whole product, why people are more honest with AI than with other humans, and what changes when the coaching conversation that used to happen at 10pm with your spouse happens with a coach who actually knows your situation.