Darren Crossett

Life Coach, Business Coach, Financial Coach


I am a husband, father and former financial services executive. I graduated from the State University of New York College at Cortland with a Bachelor of Arts degree in economics and a minor in management.  Upon graduation at the age of 20, I began my career in financial services and held various positions.  In 1986 I joined Beacon Federal and played an integral part in growing the organization from twenty-five million in assets to a one billion dollar publicly traded bank. I ended my banking career as the Senior Vice President, COO in 2012 when the bank was acquired and in 2013 formed Winmoor LLC, a coaching and business consulting practice.

How I can help

I am uniquely qualified to provide leadership, life and personal finance coaching to individuals and organizations through vision and innovation. My experience has provided me a entrepreneurial perspective with an approach that brings a systematic thought provoking style with a high degree of competency and quality. My peers describe me as a dedicated, honest, and empathetic individual who has creative ideas, and facilitates change by using a detailed and rational approach.

Who I work with

Young professionals, Executives and Individuals


“I've been through many programs such "7 Habits", Dale Carnegie and Sandler Training and consider myself a continuous learner. The thought of having an executive coach never crossed my mind until Darren Crossett invited me to explore his coaching services. Darren made a difference because his coaching was one-on-one and more in depth. His intelligent questions opened me to look at my goals and take action from a new perspective.”

- Joseph Dwyer, Chief Financial Officer, Oswego Teachers Employees FCU

“Darren Crossett is an incredible coach who is committed to improving your professional life by keeping you focused and accountable. He helps define what you want to accomplish and provides a clear vision of where you are and where you want to be. I attribute a more productive year to Darren and believe my improved skills will bring measurable results for the rest of my career.”

- Heather C., Office Manager & Registered Service Associates, High Tower

Contact Me

Charlottesville, Virginia, US


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