Webb attended Olympic Heights Community High School. Webb's parents owned a clothing business, which sparked her interest in fashion. She left Florida State University after one year, and moved to New York City, where her brother worked for Nicole Miller. Webb also began working for Miller in New York.
Webb and her brother later left New York City for their native Florida, where they opened more stores for Miller. When the two chose to end their partnership, Webb attended The Art Institute of Fort Lauderdale. She was trained in hairdressing by Toni & Guy and worked under John Sahag.
In 2010, Webb co-founded Drybar with her brother Michael Landau and her then husband Cameron Webb. By 2019, there were over 125 locations. In 2013, Webb developed a line of styling tools and products.

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