While still in college, Fernando began his career as a volunteer at the Chicago Mercantile Exchange, later working his way up in various positions there and at the Chicago Board of Trade from 1991 to 2001. In 2002, he started Chopper Trading. 
Fernando contributed to the work of the US Commodity Trading Futures Commission (CFTC), supporting its mission of fostering open, transparent, competitive, and financially sound markets. In 2010, Fernando spoke as a featured panelist on the Commission’s discussion of disruptive trading practices.
In 2013, Fernando addressed an international audience of shareholders and media at the annual Rosenblatt Global Exchange Leader Conference, an exclusive industry forum.
In 2015, Fernando sold Chopper Trading to DRW Trading Group, another Chicago-based trading firm.
In 2016, Fernando launched the Internet startup, Scoutahead, a company designed to improve corporate and professional growth and productivity through secure and advanced communication systems. Fernando is the CEO and Chairman of Scoutahead.
Fernando supports many philanthropic efforts in Chicago and the United States. He is on the board of trustees of the Chicago Symphony Orchestra and serves on the board of directors for PAWS Chicago, a no-kill animal shelter. He has also supported the Clinton Foundation, Wounded Warriors, and Big Brothers Big Sisters of Metropolitan Chicago. 
Fernando sits on the board of directors for the American Security Project, is a member of the Chicago Council on Global Affairs, and serves on the Foreign Policy Leadership Committee at the Brookings Institution. In 2011, he was appointed to the International Security Advisory Board which advised then Secretary of State Hillary Clinton, but subsequently stepped down citing excessive volatility in the international markets at the time.
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