Transformational Leadership Design

I use insightful questions and deep listening to help you find strategic solutions to close the gap between where you are now and where you want to be.

- Cassie Crosby, Founder & CEO of Iterata

an unlikely journey

I’ve been developing leaders for most of my career, while serving in the U.S. Army. I honed my own leadership skills and retired as a lieutenant colonel after leading high-performing, multifunctional teams through some of the military's most complex problems for more than twenty years. Despite my success, my own self-doubt led me to chase perfection and ultimately, to tie my self-worth to my work. It was only when I worked with a leadership coach that I acknowledged my need for external validation and began the work to learn how to lead myself.

In 2021, I founded Iterata so that I could continue to live my purpose -
to help people become the leaders they were meant to be.


In addition to my leadership development work, I’m a Small Business Mentor for the Venture Mentoring Team, focused on Economic Empowerment, and serve on the Leadership Council for the National Small Business Association and on the board of the Fellowship Housing Opportunities, a non-profit organization providing safe, & affordable housing for those living with mental illness. I’m a member of the New England Chapter of the International Coaching Federation, the Association for Consulting Expertise, and the Society of Professional Consultants. I co-authored ‘My Green Notebook "Know Thyself" Before Changing Jobs,’ a 30-day guided reflection for rising leaders.

Leadership is lonely, but you don't have to do it alone. If you’re ready to overcome that next challenge, let’s chat.