Craighead grew up in Elma, Washington and played college basketball at the University of Oregon, where she was part of the 2002 Women's National Invitation Tournament championship team as a senior.

The 2015–16 team improved from eighth to fourth place in the Mountain West Conference standings and resulted in a contract extension for Craighead.

Although San Jose State entered 2020–21 picked by fellow conference coaches to finish second in the standings, the team ended its season after only four games due to repeated COVID-19 issues.

A 1998 graduate of Elma High School, Craighead earned four first-team all-league honors in basketball and was Washington 2A Player of the Year as a senior.

[1][2] In her sophomore season (1999–2000), Craighead moved up on the depth chart, as she became the team's second-leading three-point shooter and played in Oregon's 2000 NCAA tournament first-round game, an overtime loss to UAB.

[3][4] As a senior in 2001–02 under new coach Bev Smith, Craighead started 35 of 35 games and averaged 7.9 points and 2.4 rebounds, helping Oregon win the 2002 Women's National Invitation Tournament.

[9] Following the surprise resignation of women's basketball head coach Tim LaKose,[13] San Jose State hired Craighead on September 16, 2013 to replace La Kose.

[19] Heading into the 2020–21 season, San Jose State was picked second in the Mountain West preseason coaches' poll.

[20] However, San Jose State played only four games, with a 2–2 (1–2 MW) record, before canceling the season in January due to repeated COVID-19 issues.

[21][22] In 2021–22, San Jose State had its worst season under Craighead with a 5–25 (2–16 MW) record and last place finish in conference standings.