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Hi, I'm Gerald Wynter, an award-winning artist, creative director, and content strategist with over 10 years of experience in performance, artist development, and multimedia production. I have a deep understanding of the music industry, from the artistic side all the way to the business perspective. I've been fortunate to perform across North America and collaborate with some amazing artists along the way. I also run Coldest Wynter Entertainment, where I support independent artists through content creation, branding, and rollout strategies. I'm passionate about mentoring talent and bringing creative ideas to life through music videos and visual planning. I manage everything from stage presence coaching to merchandising, always aiming to connect deeply with fans and build strong artist brands.…Hi, I'm Gerald Wynter, an award-winning artist, creative director, and content strategist with over 10 years of experience in performance, artist development, and multimedia production. I have a deep understanding of the music industry, from the artistic side all the way to the business perspective. I've been fortunate to perform across North America and collaborate with some amazing artists along the way. I also run Coldest Wynter Entertainment, where I support independent artists through content creation, branding, and rollout strategies. I'm passionate about mentoring talent and bringing creative ideas to life through music videos and visual planning. I manage everything from stage presence coaching to merchandising, always aiming to connect deeply with fans and build strong artist brands.

Gerald Wynter

Creative Director, Content Strategist, Music Composer, +1

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Hi, I'm Gerald Wynter, an award-winning artist, creative director, and content strategist with over 10 years of experience in performance, artist development, and multimedia production. I have a deep understanding of the music industry, from the artistic side all the way to the business perspective. I've been fortunate to perform across North America and collaborate with some amazing artists along the way. I also run Coldest Wynter Entertainment, where I support independent artists through content creation, branding, and rollout strategies. I'm passionate about mentoring talent and bringing creative ideas to life through music videos and visual planning. I manage everything from stage presence coaching to merchandising, always aiming to connect deeply with fans and build strong artist brands.…Hi, I'm Gerald Wynter, an award-winning artist, creative director, and content strategist with over 10 years of experience in performance, artist development, and multimedia production. I have a deep understanding of the music industry, from the artistic side all the way to the business perspective. I've been fortunate to perform across North America and collaborate with some amazing artists along the way. I also run Coldest Wynter Entertainment, where I support independent artists through content creation, branding, and rollout strategies. I'm passionate about mentoring talent and bringing creative ideas to life through music videos and visual planning. I manage everything from stage presence coaching to merchandising, always aiming to connect deeply with fans and build strong artist brands.

Available to hire

Hi, I’m Gerald Wynter, an award-winning artist, creative director, and content strategist with over 10 years of experience in performance, artist development, and multimedia production. I have a deep understanding of the music industry, from the artistic side all the way to the business perspective. I’ve been fortunate to perform across North America and collaborate with some amazing artists along the way.

I also run Coldest Wynter Entertainment, where I support independent artists through content creation, branding, and rollout strategies. I’m passionate about mentoring talent and bringing creative ideas to life through music videos and visual planning. I manage everything from stage presence coaching to merchandising, always aiming to connect deeply with fans and build strong artist brands.

Skills

Experience Level

Expert

Expert

Expert

Intermediate

Intermediate

Intermediate

Intermediate

Intermediate

Intermediate

Intermediate

Work Experience

Assistant Art Director at Budou Films – Vancouver, BC

March 1, 2025 - Present

Worked on-set for visual productions handling set decoration, prop management, and visual continuity. Built mood boards/look books and handled purchases and rentals for scene styling.

Founder / Creative Director at Coldest Wynter Entertainment (CWE)

August 1, 2021 - Present

Built a creative platform supporting independent artists through content, branding, and rollout strategies. Directed music video projects including scripting, storyboarding, casting, location and prop management. Oversaw merchandising, social media strategy, and fan-based targeted marketing. Mentored artists in vocal delivery, stage presence, and visual branding.

Musician / Host (as Grizzy Wynter) at Self-Employed

February 1, 2015 - Present

Performed across North America; opened for Tech Nine, Obie Trice, Yelawolf, Cozz, and Madchild. Played in front of 10,000+ at Freedom March 2020 and was named Buzz Music LA’s 2019 “Artist to Watch.” Won “Best International Artist” at 1st Annual Binge TV Awards with the song "Illuminate" nominated for Record of the Year at Wavy Awards NYC. Featured in Genius, Variety, HipHop Canada, and Buzz Music LA. Managed all aspects of branding, content creation, and audience outreach.