Gail was born in Zaporozhye, Ukraine and began playing tennis at age 6 after moving to Brooklyn, New York. An elite junior player, Gail won 8 gold balls from USTA National tournaments, including the USTA Billie Jean King Girls' 18 National Championships at the age of 15 which provided her a wildcard into the US Open main draw. She, also, won multiple ITF Junior titles, including the prestigious Easter Bowl in 2007 at 15 years of age. Gail was the #1 ranked junior in the United States for every age division and played at the Junior Australian Open, Junior Wimbledon, and Junior US Open.
Gail started playing professional tournaments at the age of 14. As a professional, she had a career high WTA singles ranking of 182 and competed in all 4 Grand Slam tournaments, Indian Wells, and the Sony Ericsson Open. She had wins over players such as Ash Barty, Sloane Stevens, Kristina Mladenovic, Timea Babos, Johanna Konta, and CoCo Vandeweghe. In doubles, Gail had a career high WTA ranking of 348.
After retiring from the WTA tour in 2012, Gail (along with husband Mark) developed the highly successful Junior Excellence Tennis Program at Eastside Tennis Center. In 2015, Gail returned to the professional tour. Between 2015 and 2019, Gail won 3 ITF singles titles and 1 ITF doubles title. She, also, earned a wildcard into the 2018 US Open. During her professional career, Gail won a total of 6 singles titles and 3 doubles titles. Near the end of 2019, Gail again retired from the tour and has been coaching full-time for Northwest High Performance Tennis.