When Gottlieb returned to Brown for her senior year in 1998–99, she was both a player and a student assistant, working with the coaching staff. Her teammates voted her the Team Heart and Soul Award in 1999. That same year, she was also awarded her B.A. in political science.
Because of her experience as a player-coach at Brown, Gottlieb was hired as an assistant by Syracuse University head coach Marianna Freeman, the day after she graduated from college. In the two years she spent at Syracuse, Gottlieb also earned a master's degree in the philosophy of education. Then in 2001, she moved to the University of New Hampshire, where she was an assistant under Sue Johnson. The following year, the 24-year-old Gottlieb was asked by the head coach of the University of Richmond, Joanne Boyle, to be her top assistant. According to Gottlieb, it took her "about 30 seconds" to accept.
Gottlieb worked under Boyle for three successful seasons at Richmond, 2002–05. The Spiders had three consecutive seasons with 20 or more wins. In 2003 and 2004 Richmond played in the WNIT, and in 2005 the Spiders received their first invitation to the NCAA Tournament in 14 years.
During Boyle and Gottlieb's first year at California, 2005–06, the Bears had their first winning season in 13 years and received their first NCAA Tournament bid since 1993. The Bears made the NCAA Tournament each of three years that Gottlieb was an assistant in Berkeley. In 2007, Gottlieb was elevated to Associate Head Coach.
On May 15, 2008, Gottlieb was named head coach of the University of California at Santa Barbara. The 30-year-old Gottlieb was just the fourth head coach in UCSB history, and replaced retiring long-time coach, Mark French. In her first season as a head coach, Gottlieb led the Gauchos to a 15-1 regular season conference record in the Big West Conference, and a 22-10 record overall. She was the first coach at UCSB to win 20 games in her first season. Gottlieb scheduled a demanding non-conference season, and the Gauchos pulled off a convincing 59-47 upset of Gonzaga. UCSB won both the regular season Big West championship and the conference tournament championship for 2008–09, which secured an invitation to the NCAA Tournament. The 15-seed Gauchos were knocked off by the 2 seed, Stanford, in the first round. Gottlieb was named Big West Coach of the Year for 2008–09.
During Gottlieb's second season at UCSB, the Gauchos compiled a disappointing 15-17 record. But the following season, 2010–11, the team bounced back with a 19-12 record. They won the Big West regular season championship with a 12-4 conference record. The Gauchos received an invitation to the WNIT, where they lost a close game on the road to USC in the opening round, 67-64.
Gottlieb's first team at California had no seniors, and started freshmen at point guard and forward. The Bears played a schedule filled with ranked teams, and they suffered tough losses by three points or less to #12 Ohio State, #16 Rutgers, and #24 Texas. They also took #4 Stanford to overtime on the road, before falling 74-71. They did pull off a 59-50 upset of #22 Virginia and their former coach Joanne Boyle. But Gottlieb's team came back after every tough loss to win. Their play was marked by dominance in rebounding, particularly on the offensive boards. The Bears ended the 2011–12 season with a record of 25-10. Their 13-5 record in conference play put them in second place in the Pac-12 Conference. California was invited the NCAA Tournament for the first time since 2009, as an 8 seed. In the first round the Bears beat 9-seed Iowa, 84-74. In the second round they faced 1 seed Notre Dame on the Irish home floor. The Bears played Notre Dame to a 31-31 tie at the half, but the Irish pulled away in the second half, winning 73-62.
With almost the entire team returning for the 2012–13 season, expectations were high, and the Bears were ranked #13 in the AP pre-season poll, their highest ranking since 2009. The Bears more than lived up to the expectations, compiling a 32-4 season record, and ending the regular season with a #6 ranking. The highlight of the regular season was a 67-55 road victory over arch-rival and perennial women's basketball power #4 ranked Stanford. Cal's victory broke an 81-game conference winning streak for the Cardinal. Gottlieb led the Bears to a 17-1 conference record, making them Pac-12 Conference co-Champions—the first conference championship in California Women's Basketball history. The Bears earned a second seed in the NCAA tournament, the Bears' highest tournament seed ever. They defeated Fresno State 90-76 in the first round, and downed South Florida in overtime to advance to the Sweet Sixteen for only the second time in school history. The Bears beat LSU to advance to the Elite Eight for the first time, and then earned their first trip to the Final Four trip with a thrilling 65-62 overtime victory over Andy Landers' Georgia Bulldogs at the Spokane Arena in Spokane, WA. A tough loss to Louisville in the national semifinal game concluded the team's extraordinary season. "What I said to our team in the locker room is that we can be disappointed about a half a basketball that we wish we had back. We could be disappointed to not be playing on Tuesday night," Gottlieb said. "But I'm going to think about that for two minutes, and for the next 10,000 minutes I'm going to think about what this group did for the University of California."
