Gregg has more than 35 years of experience creating and building organizations and initiatives in the private, public, and nonprofit sectors. He currently chairs America’s Promise Alliance and serves on the boards of Points of Light; The Committee for Economic Development (CED); City Year; Oxford Analytica; and The Fitzie Foundation.

Earlier in his career, Gregg served on the White House staffs of two presidents, for Richard M. Nixon as the youngest staff assistant and, 15 years later, for George H.W. Bush as Assistant to the President. Gregg helped President Bush make civic engagement, social entrepreneurship, and "Points of Light" hallmarks of his presidency. He was the founding Director of the White House Office of National Service; helped establish the Points of Light Foundation dedicated to the notion that “the solution to each problem that confronts us begins with an individual who says, ‘I can help’”; and was instrumental in the passage and signing of the National and Community Service Act of 1990 which created the Commission on National and Community Service, the forerunner of the federal corporation now known as AmeriCorps.

In the White House, Gregg created the first daily Presidential recognition program in American history, the Daily Point of Light Award. President Bush made 1,020 of these awards, each a story of an individual or group voluntarily acting on their own values and with their own liberty to make a difference in the life of another person or of a community. The awards continue through the Points of Light Foundation, and now number almost 7,000. With Gregg’s stewardship, the work expanded in 2014 to the United Kingdom where three successive Prime Ministers have awarded their own Daily Point of Light now numbering more than 1,600. In addition, in early 2018, Her Majesty Queen Elizabeth II began regularly recognizing a Commonwealth Point of Light from the 53 Commonwealth Nations and she has made more than 170 of these awards.

Following the White House, Gregg was a Visiting Scholar at Indiana University, where he led a research team in discovering a “common journey” of Points of Light through in-depth interviews of 240 of the original award winners. In addition, Gregg built and tested an operating model to increase social entrepreneurship among local residence of a low-income San Jose, California community. He was lead architect of the Presidents’ Summit for America’s Future in 1997 that engaged five U.S. Presidents, other leaders, and community delegations from across the country, and from that, with Colin Powell and others, founded America’s Promise Alliance to help the nation better mobilize itself to advance the well-being of children and young people.

Gregg was also a consultant with McKinsey & Company in New York; an officer and director of General Atlantic Energy, a private oil and gas exploration and production company in Denver; and the Colorado State Chairman of the George H.W. Bush for President campaign. Gregg is a graduate of Harvard College, Oxford University, and Harvard Business School.