This Annual Meeting features highlights from the Ambassadors’ year, stories of success from local business-people and community members, the announcement and presentation of the Everyday Awards and things to look forward to.
Tickets *Available HERE!*
2025 Annual Meeting (Celebrated 3/21/26) Speakers
Chantae Reynolds – JK Woodworked Creations
Chantae Reynolds is the owner of JK Woodworked Creations, a family-owned creative business specializing in handcrafted wood art, custom laser-engraved designs, and community-centered paint experiences.
As an artist and entrepreneur, she is passionate about creating welcoming spaces where people of all ages can explore their creativity, connect with others, and build confidence through art.
Through her work, Chantae blends craftsmanship, creativity, and community to make art accessible and meaningful.
She is also the founder of Cash Mobs, an initiative created to support and uplift small businesses through intentional community spending.
Chief of Police William H. Penn, Jr. – WS Police Department
Chief Penn began his career with the Winston-Salem Police Department in 1997. He was promoted to Corporal in 2005, Sergeant in 2009, Lieutenant in 2014, Captain in 2017, Assistant Chief in 2019, and was appointed Chief of Police in January 2023.
Chief Penn has served in the Patrol Division, Foot Patrol, Vice and Narcotics, Crime Prevention, Recruiting Unit, and as Division Commander of District One. He also served as the Bureau Commander for the Support Services Bureau. Most recently, Chief Penn served as Bureau Commander of the Investigative Services Bureau.
In 2006, he was recognized by Ashley Elementary School as Volunteer of the Year for his work in the school. Chief Penn is an Assistant Scoutmaster with the Old Hickory Council Boy Scout Troop 912. He serves as a mentor at his former high school Carver High School in Winston-Salem, NC. In August 2019, he was recognized by the HBCU Living Legends Board as one of Winston-Salem State University’s very own Living Legends. Chief Penn has served on the Liberty Street CDC Board and the HBCU Living Legends Board. He currently serves on the board of directors for Habitat for Humanity and Experience in Self Reliance.
Chief Penn is a graduate of the University of North Carolina at Greensboro and received a Bachelor of Science degree in Business Administration and earned his Master of Business Administration from Winston-Salem State University. He is a graduate of the Administrative Officers Management Program at NC State University, the Piedmont Leadership Academy in Greensboro, NC where he now instructs and has earned the trilogy award from the FBI Law Enforcement Executive Development Association. Chief Penn is a certified General Instructor through the North Carolina Justice Academy.
Chief Penn has one son. In his spare time, he enjoys spending time with his family, listening to jazz music, and cycling.
2024 Annual Meeting (Celebrated 4/12/25) Speakers
– Devin Forbes & Stephen Ewashko – Waughtown Studios
-Alexia Mitchell- Reset and Heal/The Black Mental Health Summit-
Winston-Salem Ambassadors 