Grayer joined Kaplan in 1990 as regional operations director, and held several titles before becoming president and CEO in July 1994.

[4] In 2004, BusinessWeek named Grayer one of the best managers of the year for his leadership in establishing Kaplan as The Washington Post Company’s "financial crown jewel".

[2] The company’s growth under his leadership has been reported on by other national and international media including Fortune,[5] Forbes,[6] The Wall Street Journal[7] and the Financial Times.

[8] On November 19, 2008, Grayer announced his resignation from Kaplan, stating that he plans to pursue "entrepreneurial activity, investment and philanthropy".

[9] Grayer founded Weld North in 2010 in partnership with KKR[10] to invest in education, health and wellness, media, marketing and consumer services companies.