Masai was born in Chepkoya village, Mount Elgon District. She is the third born from a family of four. She competed during her high school days while at Kibuk Secondary School. She graduated in 1988. She joined Kenya Prisons Service in 1990, known for recruiting many talented athletes. Masai did not, however, achieve anything until 1999, when she became the national cross-country champion, at the age of 32. Consequently, she started training more seriously. She won the Lotto Cross Cup Brussels in 2001 and went on to take bronze in the short race at the World Cross Country Championships that year. She improved upon this the following year, taking the gold at the 2002 IAAF World Cross Country Championships.
International career
Masai holds the 3000 metres African record set in July 2002 in Monaco She won a bronze medal at the 2003 World Championships. In 2004, she failed at the Kenyan trials for the Olympics, but since she was one of only three Kenyans who had beaten the Olympic "A"-qualifying time in women's 5000 metres that year, she was offered a place on the team. Masai herself initially rejected the offer, but joined the team after lengthy negotiations. At the Olympics she dropped out suffering a hamstring injury. She made her marathon debut at the age of 38, but gave a confident first performance, clocking 2:27:06 to win the 2005 Hamburg Marathon. She finished fifth at the 10,000 metres race at the 2005 World Championships in Helsinki, Finland. Her time, 30:30.26 was a new Kenyan record. The record was beaten by Linet Masai at the 2008 Olympics, who run 30:26.50. Masai has since been shifting from track running to marathon. She won Hamburg Marathon in 2005 and participated it also in 2006 and 2007. In 2006, she won Berlin Half Marathon, setting the fastest half marathon run that year, 1:07:16 minutes. It was also a personal best and a course record. She also set a new 5000 metres Kenyan record of 14:33.84 minutes. She won 10,000 metres silver medal at the 2007 All-Africa Games. Her time, 31:31.18 is a new World record for women over 40 years old. The previous record was held by Nicole Lévêque of France, who run 32:12.07 in Helsinki in 1994. Masai participated the 2008 World championships marathon in Osaka, Japan, finishing 8th in a race won by her compatriot Catherine Ndereba. Masai won the 2008 Virginia Beach Rock 'n' Roll Half Marathon. She won Singapore Marathon in December 2008. she broke up with her agent Dorothee Paulmann. in 2007 and worked independently. She currently lives in Ngong and Kitale. She coaches the Kenya Prisons Cross Country team. She is a divorced mother of one, her son Paul Griffin Sakit born in 1992 who ran for Louisiana Tech University. Masai retired from competitive running in early 2010 because of a knee injury.