How Cloverleaf Brings Personalized AI Coaching Into Everyday Work

In this episode of Your Next Move: Audio Edition, Inc. staff reporter Ben Sherry sits down with Darren Murriner, founder of AI coaching platform Cloverleaf, ranked No. 917 on the 2026 Inc. 5000. After spending 15 years in the corporate world, Darren launched Cloverleaf to help employees understand how they work best with others by delivering personalized coaching through familiar tools such as Slack, Microsoft Teams, email, and calendars. Darren explains how observing the dramatically different results produced by small creative teams inspired the company—and why Cloverleaf initially struggled to explain its technology to potential customers. He shares how the arrival of ChatGPT helped the company define its product as an AI coach and how Cloverleaf combines behavioral insights with multiple AI models to offer guidance tailored to individual employees and their workplace relationships. Plus, Darren discusses why successful AI pilots require measurable results, how Cloverleaf encourages adoption without forcing employees to use another workplace platform, and why word of mouth has helped the product spread from small teams throughout entire organizations. He also explains how the company hopes to make personalized coaching—which has traditionally been reserved for senior executives—accessible to frontline workers, new managers, and anyone preparing for a difficult conversation, promotion, or next career move.