Articles CHESAND GREGORY

Chesand Gregory is an award-winning educator, a multitalented, resourceful and naturally charismatic teacher, wife of a scientist, and mother of two energetic boys; The JAG Brothers with a flair for community leadership and empowerment.
She is the author of Did Santa Wear A Mask. Her book was inspired by her 4-year-old son when he asked the question that moved her, “Mommy, will Santa wear a mask?”. Did Santa Wear A Mask, which was endorsed by Amazon – Featured on ABC, FOX, NCB news outlets.

Chesand Gregory has developed a recognized reputation and can regularly be seen putting her different talents to use, as a singer and model. Most recently she has been signed on with one of Toronto’s top modeling and talent agency, Carolyn’s Model and Talent for print, commercials and voice work.

She is well recognized for her work with several prominent brands based in Canada, the US. Gregory has worked with The American Girl® Doll Company to depict Melody’s mother in their book; Melody – No Ordinary Sound. She was also featured in the Loblaws® Celebrate your kitchen catalogue and as a lifestyle model for other well-known brands including, Leg Master® and Body Glove®.

The entrepreneur, who had dreamed of owning her own company since she was 13 years old, launched her company, JChess Designs, in 2014. She focuses on the natural and matriarchal side of beauty. Her company was inspired eight months after having her first child. Chesand introduced her community to her Boobie Covers, a practical solution, supplying an essential tool for lactating mothers. Her company not only offer mothers the ability to breastfeed discreetly in comfort, but it’s also more hygienic to use it in areas such as public restrooms or waiting areas in clinics and hospitals where sick persons are often coughing and sneezing nearby. These common dilemmas, combined with how shy most mothers are about breastfeeding in public, highlight the need for her covers and how useful it would be to moms.

Gregory’s supportive nature and passion for breastfeeding go even further in her drive to help create awareness in her community. Through the promotion of her company, an educator, Chesand launched her first charity event and visited hospitals to educate new mothers on breastfeeding, its benefits as well as donating gifts of maternity-related products from JChess and other sponsors to mothers in need.

She is the titleholder of The Red Blazer Award for Women in Entrepreneurship, 2021, The Edna Scott Award for the Greatest degree of Diligence in Teaching, 2012 and The Ken Gray Award for innovations in Teaching, 2012 In 2020. Chesand’s impact as a business leader has been consistently touching many lives in her community. With a host of educational achievements and award, Chesand been sharing her knowledge and expertise to mentor other women, especially those raising young children, to see their potential and launching their businesses without FEAR.

To also make a difference in her community the philanthropist has extended her parenting and teaching beyond storytelling, collaborating with charities such as Jamaica Helping Hands Foundation and Toronto Foundation for Student Success. A portion of the proceeds from the sale of her book Did Santa Wear A Mask, is donated to provide children with immediate educational support and build schools in Jamaica.

Please consider Mrs Chesand Gregory, a hidden hero in our community as she continues to inspire other women to reach new heights for the following awards: The Authentic Leader Award, Innovation Award Inspire Award, Millennial Leader Award Rising Leader Award and the Black Women Leader Award. Thank you for reading.