

Founder's Story
Founded by Cherill Dawson, Stiletto Strategist is an organization that connects, educates and supports women and children of all ages and backgrounds, and inspires them to give back to their communities through mentorship, networking and volunteerism. Through her drive Cherill has nurtured a dream that is shaping lives.Stiletto Strategist is built on a passion to inspire all women, and even in its infancy it has touched hundreds of members throughout Greater New York. The direction the organization is headed is simply… empowering.
Every cloud has a silver lining… Cherill Dawson is an example of a strong woman that turned her tragedy into a triumph. Through being sheltered growing up, only things she knew was education, then entering a world at 16 she knew so little about. After voiceless years of letting others dictate her life, though their intentions were good, she finally had the strength to leave home – against the will of her family – and began a journey of discovery, of herself and the world around her. It was scary, it wasn't always pleasant, and it was not easy. However it was a decision she made – finally – for herself. It was the beginning of something amazing. She not only found her voice, she found her calling.
Cherill wanted to create a safe haven for other women with similar pressures, facing adversities, low self-esteem, and uncertainty. Stiletto Strategist began as a small group with light hearted activities connecting like-minded women. It had more potential. It then became a group built by social media and incorporated volunteerism. There was still more that could be done. Today Cherill leads an organization that includes professional development workshops as well as job placement, health awareness, volunteerism for women and young girls, financial growth, business guidance, networking and mentoring. It grounds women looking to build relationships, fosters women looking to further themselves, and encourages women through the strength of paying it forward.
Cherill is an extremely dedicated woman determined to continue her vision. Inspire. Empower. Community. Her story and commitment to her cause is truly is admirable. We are very excited to see what lies ahead in the next chapter…
