Her earlier career included executive roles at Ralph Lauren Corporation and Nike, and she was also CEO of HSN from 2006 - 2017.

[1] Her adoptive parents were Donald and Elaine Waldman, a Jewish produce dealer and homemaker on Long Island, New York, who had married young but had been unable to have children.

However, in her senior year at George Washington University, she broke off her engagement to her high-school boyfriend and dropped her plans to attend law school, and instead moved to New York City to go into the fashion industry.

[20] She brought her strong fashion background to Nike's apparel and regenerated it, devoting much of her energy to the company's weaker women's wear business.

[19] HSN had had seven CEOs in the previous 10 years, and according to Grossman the company, offices, and employees seemed downtrodden and frozen in time.

[11] One of her first actions was to throw out all the old, broken, or dirty office furniture and give all employees Aeron chairs.

[11] In order to focus on revitalizing HSN, she closed IAC's failing UK auction business, sold its German shopping channel, closed the down-market DirecTV clearance-shopping channel America's Store, and put another executive in charge of Cornerstone brands.

[23] By October 2006 she rolled out HSN's new brand image, tagline, vision statement, customer intention, and advertising.

[23][24] By mid 2007 the relaunch and redesign of HSN's channel, website, and campus were in effect, and the business started to turn around.

[27][28][29] She continued to aggressively transform, redefine, and reinvent the HSN brand, improving its demographics and increasing the value of its stock from $10 at its IPO in August 2008 to $55 a share in 2014.

[4][35][36] Forbes and Fortune termed the new brand a "hybrid" – a media, entertainment, technology, and retail business.

[33][35][34] She recruited major celebrities such as Jennifer Lopez, Queen Latifah, Mariah Carey, Iman, P. Diddy, Padma Lakshmi, Martha Stewart, Jessica Simpson, Keith Urban, Nicki Minaj, Mary J. Blige, and Serena Williams, and major cosmetics companies such as Lancôme and Stila, to appear on the network and sell their own brands of merchandise, most of them exclusively created for HSN.

[11][23][24] She also created partnerships with major companies like Disney and other Hollywood studios to sell merchandise, invited movie and television-series tie-ins, and aired live concerts by singers such as Rod Stewart and Randy Travis.

[49] Once in office, she said that her plan included a push beyond dieting and into well-being, as well as a partnership with Oprah Winfrey, who holds almost 15% of WW's shares and sits on its board of directors.

[56] She is a member of the Industry Advisory Board of the Jay H. Baker Retailing Center at the Wharton School of Business.

[59][60] In June 2017, Grossman joined the Board of Directors of sports apparel e-commerce retailer Fanatics.