From 1985 to 2009, Jaramillo also worked as the tennis director for the IMG Academy Bollettieri. There, he helped develop many multi-sport training programs and served as Nick Bollettieri’s right-hand man. For 26 consecutive years, Jaramillo coached players at all four Grand Slam events — the French Open, Wimbledon, the Australian Open, and the U.S. Open.
Currently, Jaramillo is the co-owner of Club Med Academies in Port Saint Lucie, Florida, an elite training facility which provides high-intensity skill development in tennis, golf, volleyball, soccer, and swimming as well as the arts and academics. The center’s professional coaches and specialists work with some of the world’s top athletes, including gold medalists and world champions. Under Jaramillo’s guidance, junior players aspiring to attend top-tier universities have secured millions of dollars worth of scholarships.