Colleen Barrett

In 2008, Barrett stepped down as president of the airline, passing the title to then-CEO Gary C. Kelly. Kelleher passed his title as Chairman to Kelly at the same time. Barrett and Kelleher were titled, respectively, President Emerita and Chairman Emeritus. They both chose to remain with the company. Barrett enjoyed returning to a regular employee role and continued to work in customer service and employee development roles for the next 5 years. Though she and Kelleher stepped away from day-to-day involvement in 2013, she remains involved with the airline in her emeritus role.

Barrett's leadership was not without some missteps along the way. She has acknowledged the failure of her effort to create bereavement fares at the airline. She generated some criticism for the airline in 2007 when she publicly defended an employee's decision to forbid a customer from boarding a flight for wearing a mini-skirt.

In March 2001 Kelleher, who had been serving as Chairman, CEO, and President, retired from the latter two positions, passing the CEO role to James Parker and the president role to Barrett, who was also made chief operating officer. With this promotion, she became the first and then-only woman to hold the office of president at a major airline, and the highest ranking woman in the world of aviation.

Barrett's level of authority at the airline quickly grew. At first this authority came simply from the high level influence she had with Kelleher as his secretary, though she eventually gained more formal recognition as Vice President of Administration in 1986 and a position on the Executive Planning Committee. She was promoted to Executive Vice President of Customers in 1990. Barrett described her transition to true leadership as a gradual process, and for several years even after she had been promoted beyond an assistant to Kelleher she had to occasionally remind board members and other senior leaders at the company that she was a distinct leader and not "just a parrot of what Herb thinks". Despite Kelleher's role as the more public face of the company, employees universally referred to "Herb and Colleen" together as the leaders of the company.

In 1967, Kelleher had met with Rollin King, who had pitched the initial business plan for Southwest Airlines and the two had begun their efforts to begin the company. Kelleher's role was largely focused on serving as legal counsel to the new airline during the many early court battles the airline faced before beginning service. Barrett was closely involved with every step of the legal process. After four years of court battles they succeeded and the first Southwest Airlines flight finally took off June 18, 1971. For the first seven years of operation, Kelleher and Barrett supported Southwest through continued legal support as Kelleher remained an active lawyer, though also with a seat on the Southwest board. However, after a leadership restructure in 1978, Kelleher became chairman of the board and temporary CEO (becoming full-time CEO in 1981). Kelleher brought Barrett with him once again and she remained his secretary and advisor. When they transitioned to Southwest full-time, they both took a leave of absence from the Oppenheimer law firm that technically was never cancelled the remainder of their careers.

In 1968, several years after graduating from Becker, Barrett got a job as a legal secretary working for Herb Kelleher when he was a young lawyer at Wilbur Matthews’ law firm in San Antonio. Kelleher had a reputation as a skilled, but chronically disorganized lawyer, whose office was in such disarray that a night guard at the firm once called the police assuming a break in had occurred. Barrett's first duty was to set up a filing system to organize ten years-worth of his case files. She grew to play a pivotal role in keeping Kelleher organized, setting him up for his eventual success as both a lawyer and businessman over their 51-year working relationship. Despite the title of secretary, Barrett was treated as an equal and trusted advisor who regularly joined Kelleher in court. When Kelleher left Matthews’ law firm to help found the law firm of Oppenheimer, Rosenberg, Kelleher & Wheatley in 1970, Barrett moved with him.

Colleen C. Barrett (born September 14, 1944) is the President Emerita of Southwest Airlines, and an influential figure in the founding and development of the company. In 2001 she became the first woman to serve as president of a major airline.

Barrett was born in 1944 to a lower-income family in Bellows Falls, Vermont. She attended the Worcester campus of Becker College, where she graduated in 1964 with a two-year degree to become a legal secretary. In 2015, she donated US$1 million to her alma mater for the founding of a center for innovation and entrepreneurship. The center opened in April 2018.