Rachel Simmons

Rachel Simmons is an executive coach, master facilitator, and New York Times bestselling author who has spent the last decade coaching leaders from Director through C-suite levels
across some of the world’s most innovative organizations, including Google, PayPal, and Capital One.

Rachel works with leaders who sense that the patterns and habits that fueled their early success may no longer be serving them. In a time of unprecedented complexity, she helps clients examine how they lead teams, navigate uncertainty, and think about their own purpose, ambition, and future. Her approach focuses on helping leaders understand and upgrade their
“operating systems”—the habits, assumptions, and mindsets they unconsciously rely upon to succeed.

Known for being direct, warm, and practical, Rachel listens closely, surfaces patterns quickly, and helps clients translate insight into meaningful action. Each coaching session has a clear focus while remaining flexible enough to address what matters most in the moment. Rachel works with the whole person, recognizing that how we lead is shaped by the stories and experiences we carry.

As an associate with Cultivating Leadership, Rachel teaches complexity fitness and helps leaders build the capacity required to thrive in rapidly changing environments. A lifelong athlete,
she believes growth often requires stepping into discomfort and supports clients in doing so with courage and intention.

Rachel is the author of Odd Girl Out, The Curse of the Good Girl, and Enough As She Is. She serves on the faculty of the Google School for Leaders and is an ABC News Contributor for Good Morning America. Her writing has appeared in The New York Times, Harvard Business Review, and numerous other publications.

Rachel loves mountain biking in her free time and lives in Western Massachusetts with her family.