Kenneth was born in Mineola, New York, USA, in 1951 to a dentist and a dental hygienist. Kenneth honed his leadership skills as class president at the Waldorf School in New York and went on to earn a bachelor’s degree in history from Bowdoin College, followed by a J.D. from Harvard Law School. He worked in a law firm and a management-consulting group from 1977 to 1981, and then went to work for American Express in 1981. Although the company is largely known for its credit-card services today, Kenneth revived the merchandise services division in the 1980s, replacing the cheap goods American Express offered with finer items, including durable luggage and personal accessories. In 1997, Kenneth was appointed COO and president of American Express; he became CEO in 2001.

American Express employed 4,500 people at its lower Manhattan headquarters at the time of the September 11, 2001, terrorist attacks, and the company lost 11 staff members. Kenneth had only recently taken the reins as CEO and had to the guide the company through tumultuous waters. The company’s travel business suffered, but under Kenneth’s leadership, American Express began offering small business services, proving the company’s ability to evolve and innovate. American Express also began to partner with banks to offer credit cards. This led to legal disputes with two other major credit-card companies, which offered credit cards through exclusive deals with banks, barring the financial institutions from partnering with and issuing cards through other credit-card companies.

In 2003, American Express came out on top, and Kenneth secured partnerships with more than 85 banks in more than 90 countries over the next three years. During the worldwide economic recession in 2008, which included a global credit crisis, the U.S. Federal Reserve System approved American Express as a licensed bank holding company, enabling the company to receive relief through the Troubled Assets Relief Program (TARP), which allowed the U.S. Treasury Secretary to purchase troubled assets from banks to restore stability and liquidity to the U.S. credit markets. Kenneth drew well-earned praise for guiding American Express through the economic crisis and restoring investor confidence, and he continued to serve as CEO until he stepped down in 2017.

Following his tenure at American Express, Kenneth became chairman and managing director of General Catalyst Partners, a venture-capital firm. He has also served on the board of directors for several companies, including Airbnb, Facebook—the first African American person to do so, and Berkshire Hathaway, where he replaced Bill Gates. He was inducted into the Global Business Hall of Fame in 2002.