Randall is a serial entrepreneur and venture capitalist. Randall is a co-founder of Akamai Technologies, a content delivery and security software company that serves nearly 30% of the world's web traffic, is a member of the S&P 500, employs nearly 8,000 people with 64 offices in 28 countries, and had $3.45 billion in 2021 revenues.

Randall is also the founder and CEO of Sandee, a travel company focused on the promotion of beaches and beach tourism around the world whose mission is to create the world's first beach brand; the co-founder and Co-CEO of Thrive Properties, a real estate investment firm specializing in the ownership, management, leasing, and redevelopment of properties in primary markets throughout the United States; and the owner and CEO of CollarCard, LLC, a promotional products company that makes patented men's collar stays that are sold throughout the world.

Randall is also the founder and CEO of JUMP Investors which functions as his family office. Since its formation in 1999, JUMP has invested in more than 80 early-to-late- stage technology companies including Google, Seagate, Lyft, and Chime. JUMP is also an active investor in real estate, private equity, hedge funds, and public equities.

Over the past 20 years, Randall has been an advisor to more than 50 companies, has served on the board of directors of many companies, has been an active public speaker, and has mentored more than 200 students through JUMP's annual summer internship program.