Wentworth held a human resources management position at PepsiCo. before he joined Mary Kay, Inc. During his 5-year tenure, he served as senior vice president of human resources and then president, international. He later became group president for employer and key accounts at Medco Health Solutions Inc. Wentworth was also CEO and president of Accredo, Medco's specialty pharmacy. In April 2012, Express Scripts Holding Company acquired Medco for $29.1 billion. As part of the merger, Wentworth, then vice president of sales and account management, joined Express. He served as head of sales and account management operation and senior vice president before he was named president of the company in January 2014. In September 2015, Wentworth was named CEO of Express Scripts. Previous CEO George Paz became the company's chairman. After the Merger of Express Scripts with Cigna in December 2018, Wentworth became the president of both companies.
Philanthropy
The Wentworths established a scholarship fund at Monroe Community College for business and music majors and gave the school a Steinway piano in 2009. In 2010, they established the Wentworth Family Endowed Scholarship at the University of Rochester, the school two of their three children attended, which supports students transferring from community or junior colleges. In 2012, after a $1 million donation to the school, the Wentworth Atrium in the Raymond F. LeChase hall of the University of Rochester's Warner School of Education was named for the Wentworths. The couple are members of the George Eastman Circle, the University of Rochester's giving society, as well as the University's Parents Council. They also serve as co-chairs of the Parents Initiative for the Meliora Challenge. In May 2013, Wentworth was named to the University of Rochester Board of Trustees. In November 2013, the Wentworths gave MCC $2.25 million which would be processed through the Monroe Community College Foundation and award full scholarships to 40 MCC students annually. This was the largest single donation in MCC's history at the time. They also donated $3 million to the University of Rochester's Institute of Data Science in 2015. In 2018, Monroe Community College announced a $50 million scholarship fund, which was led off with a $4 million donation from the Wentworth family.
