Pickett has held various leadership roles at HomeSide, and its predecessor companies, BancBoston Mortgage Corporation and Mortgage Corporation of the South. Under his leadership, the servicing portfolio grew from $11.5 billion to its current size of over $185.5 billion. The company grew from a small, regional mortgage company with 850 employees to one of the largest mortgage companies in the US with over 3000 employees worldwide. In addition to his role as Chairman at HomeSide, Pickett has also been active in industry and community organizations. Pickett served as president of the Mortgage Bankers Association of America (MBA) in 1995, and is currently a member of the Fannie Mae Board of Directors. He holds the Certified Mortgage Banker (CMB) designation conferred by the MBA, as well as the MAI designation, which is conferred by the Appraisal Institute. He also serves on the Board of Directors of Baptist Medical Center and the I.M. Sulzbacher Center for the Homeless, in Jacksonville.