Previously, he held the position of CEO at Hudson River Capital Holdings, a private investment company based in New York. Additionally, Pickett served as president of Zones, a global IT company with a revenue of $2.4 billion. He joined Zones following its acquisition of nfrastructure, a technology company he founded and where he served as CEO and chairman of the board. Pickett's leadership at nfrastructure led to the company being named The Business Review's Company of the Year by the Albany Business Review in November 2011.

In 2016, Pickett's company, nfrastructure, was recognized as one of only 48 CRN Triple Crown Winners, appearing on the Solution Provider 500 list, the Fast Growth 150, and the Tech Elite 250. Prior to nfrastructure, he co-founded CIGNA Software Sciences, a fintech company specializing in expert systems and decision support, which was later acquired by Alltel Information Services.

Pickett's commitment extends beyond business to philanthropy and community service. He has served on the boards of the Albany Medical Center and the local Saratoga chapter of Gilda’s Club. Pickett is also a member of the board of directors for his alma mater, Rensselaer Polytechnic Institute, where he was the youngest member ever appointed to the board at the time. Additionally, he serves on the boards of aptihealth, The Pickett Family Foundation, and Albany Medical College.