Uber: Travis Kalanick (CEO)
Why this is a big quit:
Over the past decade, few companies transformed the landscape of their industry the way Uber did. Travis Kalanick, the co-founder and CEO of the transportation technology company, whizzed past municipal taxis as the transportation of choice for both drivers and passengers around the globe. With Kalanick in the driver’s seat since its founding in 2009, Uber took the fast lane and raised more than $14 billion  from investors, pulled ahead of the stiff competition (Lyft, Gett, etc.), and turned Uber into a verb. More recently, Uber established its footing in the race to curb its customers’ appetites with UberEATS.
Why this is not as big as the top 10:
With all that the Uber accomplished under Kalanick, it’s hard to ignore the bumpy road Uber travelled on its journey. Kalanick was urged by investors to take the nearest exit for the culture rife with harassment and discrimination, a lawsuit claiming intellectual property infringement from Google’s Waymo self-driving unit, an argument with an Uber driver caught on tape, and more. Under these conditions it, Kalanick’s departure became nearly a pre-requisite to endure. Uber’s Board felt compelled to shift gears and steer away from its declining reputation, so Kalanick stepped down as CEO to hand the keys to Dara Khosrowshahi, previously the CEO of Expedia. With a long road ahead and new CEO in place, Uber plans to take the high road from here.