Stephenson was born and raised in Wilmington, Delaware, and graduated from Harvard College with a degree in economics.

[2] Stephenson has also served as a director of BigTray, LandaCorp, BenefitPoint, Chapters Online, Chipsoft.com, Sequana Therapeutics, Adesso Healthcare Technology Services, and SteriGenics International.

[3] In 2001, Stephenson led an effort to attract Silicon Valley executives to the Republican Party.

[1] He has been active in many organizations which included Conservation International, the Council of American Ambassadors, the Woodrow Wilson International Center for Scholars, the Lincoln Club of Northern California, and the John F. Kennedy Center for the Performing Arts.

[12][13] He formerly served on many boards and committees that were part of the Tufts New England Medical Center in Boston.