About Me

I’m a big feelings nerd and a highly sensitive person. I am deeply curious about people’s internal experiences and passionate about self-compassion. I’m really good at helping people tell the truth about themselves and their needs, even when it’s scary.

Most of my career has been in operational healthcare leadership roles—including managing a $50 million P&L as an early Regional VP at Oak Street Health. I’ve overseen large teams, worked in rapidly scaling startups, and held Head of HR / People Operations leadership roles.

I also struggled with chronic migraines from the time I was twelve into my early thirties, until I discovered a deeper understanding of how my stress, early childhood experiences, and self-criticism was showing up as pain in my body. Meditation really helped. I completed a two-year Mindfulness and Meditation Teacher Training ten years ago and am a Certified Wayfinder Coach. Throughout my career, I’ve found the most joy in serving others —helping leaders at mission-driven companies work effectively together and supporting individuals feel more at home in their bodies and more trust in themselves.

I’ve been building Jessica Dixon Coaching over the past 8 years, as my husband and I raise our two children together in Chicago.