I gather driven, ambitious, successful people, and provoke their thinking
I help clients go beyond tactics to create deep impact, clarity, and the joy of building a life and business that aligns with their vision and values.
I’m Stephen Leonard—executive coach, founder, and lifelong student of transformation. I coach leaders who aren’t just growing their organizations—they’re growing themselves.
I have been a leader and coach for 30 years in non-profit and for profit spaces. I spent 15 years leading Leonard Group, Inc.—scaling it from a hobby business to a multi-brand company generating 8 figures a year. I know firsthand the thrill and toll of leadership: the cost of vision, the complexity of growth, and the risk of losing yourself in the process.
Coaching, for me, is sacred work. It’s about helping leaders return to their calling, expand their impact, and design lives that are both wildly productive and deeply meaningful.
My Journey
Over the past two decades, my journey has taken me through:
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Pastoral leadership in growing churches and communities
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Nonprofit mobilization, organizing thousands across churches for practical impact
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E-commerce entrepreneurship, building best-in-class brands and teams
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And now, executive coaching, where I draw from every chapter of my life to serve leaders on theirs.
I bring the heart of a pastor, the mind of a strategist, and the eye of an entrepreneur into every coaching relationship.
Who I Work With
If you’re a leader asking:
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“What’s next?”
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“What am I really capable of?”
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“How do I expand my impact without sacrificing my integrity?”
Then we may be a fit.
Many of my clients are navigating inflection points: scaling businesses, stepping into greater visibility, or designing their next chapter. Some want to create more wealth or freedom. Others want to reawaken joy. All of them are committed to growth.
Let’s Talk
Coaching with me isn’t casual. It’s intentional, tailored, and focused on what matters most. If you’re serious about transformation, I’d love to explore what’s possible together.
Let’s start a conversation → BOOK A CALL
Hey Stephen-
Happened upon both you and your wife’s jewelry brand which led me to your blog and Twitter. Read your heartfelt blog and truth be told, I love kids– and David seems very, very adorable. I’m super passionate about working with kids w/ disabilities– was paired 1:1 with the best kid ever who has Angelman syndrome during the summer in high school! Are you familiar with Special Books by Special Kids (SBSK)? SBSK is my favorite media source to learn about people with differences– their YouTube videos are my favorite. I’m super familiar w/ CdLS but will watch and learn about it after the workday! I made a donation to SBSK in David’s honor 🙂 I originally went to school to become a special education teacher but later chose the business school route. Would love to talk business with you– my forte is performance marketing (SMS & email). Typically, for partners like Kendra Scott, Gorjana, etc., Wunderkind’s tech drives total digital revenue by +7%. Would love to be a resource for online rev growth. Let me know if you want to chat briefly!