Theresa Sullivan
Professional Certified Coach | Founder of Wayfinder Advising
I’m a leadership and career coach who works with thoughtful, high-achieving professionals navigating change — in their careers, their leadership skills, and their lives.
I founded Wayfinder Advising in 2012 after more than two decades in consulting, executive sales, and relationship management. I hold business degrees from the University of Notre Dame and Northwestern University (MBA, MS), and I’ve led teams, advised executives, and served as an elected official — experiences that shaped how I think about influence, complexity, and what it really means to lead with integrity.
Since then, I’ve worked with hundreds of clients in industries across the globe — especially in tech, finance, and sales — who are asking important questions about what’s next. Many are in the midst of leadership transitions, career shifts, or personal inflection points. Others are navigating burnout, imposter syndrome, or challenges in their relationships or identity.
What they have in common is a desire to lead with more intention — to make decisions they believe in, and to feel less alone while working through all of it.
My coaching style is warm, direct, and honest. I’m here to help you feel seen and supported — and also to challenge you when something’s not adding up. I coach with humor, a little edge, and a deep belief that you’re capable of more than just surviving the day-to-day. You can expect deep listening, occasional swearing, and someone who isn’t afraid to speak hard truths when it matters.
Outside of coaching, I’m mom to three teenagers, an avid reader, nerdy podcast listener, and a near-professional green tea drinker. I live in a suburb of Chicago, aspire to have Taylor Swift’s entire lyrical catalog memorized one day, and believe that humor, honesty, and human connection are essential to both good leadership and a good life.
I’ve written several articles on LinkedIn that might be of value to you in finding out more about my practice and philosophy.