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Bob Ross has held a variety of positions in the finance and accounting fields since 1997. Bob began their career at Urban Outfitters as Chief Accounting Officer, EVP Finance, Worldwide Controller, Treasurer and CFO, where they were responsible for a full range of internal and external financial reporting and analysis, budgeting, financial planning and analysis, Sarbanes Oxley Compliance, treasury and supply chain finance, tax planning and compliance, inventory control, purchasing, risk management and benefits administration, financial services, international financial operations and statutory reporting, investor relations, and strategic planning. During their tenure, they were instrumental in growing revenue from $100 million to over $2 billion.

In 2010, Bob joined ideeli, Inc. as Chief Financial Officer, where they were the leading U.S. executive. Bob then held the same position at Nasty Gal from 2013 to 2017. In 2017, they moved to Hudson Jeans; Robert Graham; SWIMS as Chief Financial Officer. Most recently, they have been the CEO of DIFF Eyewear since 2019.

Bob Ross attended Drexel University from 1986 to 1991, where they earned a Bachelor of Applied Science (B.A.Sc.) in Accounting and Finance.