On April 16, 1940, he was hired by the United States Weather Bureau. First assigned as a junior observer of meteorology at Brownsville, Texas, he was then temporarily assigned to Swan Island. After the Pearl Harbor attack, he was promoted to forecaster at the New Orleans office. As part of a United States Weather Bureau scholarship, he did graduate work at the University of Chicago in 1943 and 1944. After a stint as a hurricane forecaster in Miami under Grady Norton, he was assigned to help create the Army Air Force weather school in Panama. There he had his first flight into a tropical cyclone. After the war, he persuaded Air Force Hurricane Hunters to allow him to fly along on what he called 'piggy back missions', where he would take scientific observations using the primitive instruments. Following VJ day and the dissolution of the weather school, Simpson returned to Miami. He was then assigned to Weather Bureau headquarters, working directly for Dr. . In 1949 Reichelderfer assigned Simpson to Hawaii to be in charge of consolidating the Weather Bureau's Pacific operations. There he founded a weather observation station on Mauna Loa, studied Kona lows, and flew a research mission into Typhoon Marge aboard a specifically equipped Air Force weather plane. He continually urged Weather Bureau management to fund modest levels of hurricane research, but budgets during the early 1950s didn't allow this. Then the devastating 1954 Atlantic hurricane season changed the minds of several New England congressmen, and a special appropriation was passed to improve the Weather Bureau's hurricane warning system. Reichelderfer appointed Bob Simpson to head up the National Hurricane Research Project in 1955.
Late career
For the next four years, Simpson navigated NHRP through the shoals of bureaucratic uncertainty. Once NHRP was assured longevity in 1959, Simpson left the Project to finish his doctorate in meteorology at the University of Chicago, studying under his friend Dr. Herbert Riehl. On completing his degree in 1962, he returned to Washington to become the Weather Bureau's Deputy Director of Research, where he helped establish the National Severe Storms Project. In 1961 he obtained a National Science Foundation grant to study seeding hurricanes with silver iodide. He put together an experiment using NHRP and United States Navy aircraft to seed Hurricane Esther. The encouraging results led the Weather Bureau and the Navy to start Project Stormfury in 1962, with Simpson as Director. He headed up the Project for the next three years, including the seeding of Hurricane Beulah in 1963. He married Joanne Malkus in 1965 and persuaded her to take over as Director of Stormfury for the next two years as he became Director of Operations for the Weather Bureau. In 1967 Simpson became Deputy Director of the National Hurricane Center. Simpson reorganized NHC, making it separate from the Miami Weather Bureau office, and established the position of 'hurricane specialist' for NHC's senior forecasters. He directed NHC from 1968 to 1974, during which time he co-developed the Saffir-Simpson Hurricane Scale with Herbert Saffir, established a dedicated satellite unit at NHC, studied neutercanes, and began issuing advisories on subtropical storms. His controversial remarks to Vice President Spiro Agnew in the wake of Hurricane Camille led to an upgrade of the Air Force and Navy Hurricane Hunter squadrons, and persuaded NOAA to improve their hurricane research aircraft.
Retirement
He retired from government service in 1974, turning NHC over to his Deputy Director Neil Frank. The Simpsons returned to Washington, where they established a weather consulting firm, in Charlottesville, Virginia. At this time he became a Certified Consulting Meteorologist. Both he and his wife joined the faculty of the University of Virginia in the Environmental Sciences department. In that capacity, he participated in several international scientific experiments, such as GATE, MONEX, ITEX, and Toga COARE. He co-authored the book "The Hurricane and Its Impacts" with Herbert Riehl, and recently was senior editor and contributing author to "HURRICANE! Coping with Disaster." He was an Honorary Member of the American Meteorological Society and a Fellow of the Explorers Club of New York. He is the recipient of Gold Medals from both the U.S. and from France, and of the Cleveland Abbe Award from the AMS. Simpson, whose wife died in 2010, resided in Washington, D.C. until his death after a stroke on December 18, 2014.