Bankoff joined AOL in 1995, hired by Ted Leonsis. He held various roles and worked on a variety of brands and products during his tenure, including AIM, AOL.com, AOL Music, FanHouse, MapQuest, Moviefone, and Netscape. He focused on the company's digital content business, and helped the company acquire Engadget. He is also a co-founder of the celebrity news website TMZ. Bankoff became director of business development for AOL Greenhouse in 1996. He was named vice-president of strategy and operations for the AOL brand in 1998, and oversaw business strategy, category management, and content acquisition. He also directed AOL Music and AOL Plus. After AOL and Netscape merged, Bankoff worked to merge the two companies, and created strategic plans for Netscape. He became president of Netscape in 2001, and was responsible for business operations and the growth of Netscape.com and Netbusiness. He then served as president of AOL Web Properties, managing various AOL brands, including AIM, CompuServe, ICQ, MapQuest, Moviefone, and Netscape. Bankoff held the role of executive vice-president of programming and products starting in 2002. In 2006, he earned the first Emmy Award for his Achievement in Video Content for Non-traditional Delivery Platforms, for serving as a co-executive producer of "Live 8 on AOL", a webcast of the 2005 Live 8 concerts. Bankoff left AOL in late 2006, and began working as a consultant. Among his clients were The Huffington Post and the sports news website SB Nation, starting in 2008.
After advising and serving as an angel investor for SB Nation, Bankoff led the company through its first round of financing. He became chairman and chief executive officer in January 2009. He expanded SB Nation's network and number of writers. SB Nation was rebranded as Vox Media in 2011. Bankoff has been credited with growing the company by acquiring and launching brands. In his role as chairman and CEO, Bankoff oversees the company's eight brands, including Curbed, Eater, Polygon, Racked, Recode, SB Nation, The Verge, and Vox, and other businesses. In 2015, Bankoff was included in Washingtonian list of the "100 Top Tech Leaders" in Washington, D.C., and ranked number 18 on Business Insider "Silicon Alley 100" list of the "coolest, most inspiring people in the New York tech industry". He was also included in The Hollywood Reporter list of "The 35 Most Powerful People in New York Media" in 2016. Bankoff is a co-executive producer of a cuisine and travel television series developed by Vox Media, called No Passport Required. The series was ordered by PBS in October 2017, and is scheduled to premiere in 2018. Bankoff ranked number 67 on Mediaite's list of the most influential figures in media during 2017.