Herbie graduated, Cum Laude, from the New York Phoenix School of Design, and he took post graduate courses at Pratt Institute. The artist worked in the advertising field, honing his skills in technical rendering and designing. His accounts included Colgate Palmolive, Texaco, Sherwin Williams Paints and Hertz.

In 1968, he opened his own gallery in Port Antonio, Jamaica. There he worked mainly in oil and acrylic to portray the people and scenes of his native Portland parish. His watercolor career began after meeting Tony van Hasselt. This meeting resulted in Herbie's introduction to and instruction from other fine artists such as John Pike, Herb Olsen, Ed Whitney, Tom Hill and Robert Wood. Working closely with these fine painters, Rose had the opportunity to see how the same subject can be handled in many different ways and styles.

Moving to Sarasota/Bradenton, Herbie soon became well-known for his Florida scenes with a Caribbean flair, his flamboyant style has earned him many ribbons. In 1985 he designed a prize-winning poster for Murray-Chris-Craft celebrating their centennial. This poster was later used to promote the restoration of the Statue of Liberty.

His paintings and prints are part of collections throughout the United States, Canada and Europe, and were used to promote Jamaica during the Summer Games 1992 in Barcelona, Spain. Rose teaches classes at the Ringling School of Art and Design in the Continuing Education Program and the Manatee Art League. He provides private instruction in his studio, and he returns to Jamaica annually to conduct a workshop