Since its founding in 2007, the organization has worked to raise awareness and encourage women to become truck drivers. In 2008, WIT held its first reception at the Mid-America Trucking Show in Louisville, Kentucky. Ellen Voie, as founder, later became the President and CEO of the organization and Leigh Foxall was named chairwoman.[19] In 2010, WIT held its first annual “Salute to Women Behind the Wheel”[20] and that same year gained a monthly feature on SiriusXM's Freewheelin’ show.

Mark Rousseau joined the board as the first male director in 2010. The board of directors is composed of industry leaders from major corporations such as Walmart, Daimler, Bendix, C. H. Robinson, Arrow Truck Sales, Peterbilt, Ryder System, Michelin, J.B. Hunt, FedEx and more. In the same year, Women In Trucking founded a scholarship program to strengthen education in the commercial transportation industry.

In 2012, WIT was recognized by the White House as a “Transportation Innovator Champion of Change!”[22][23] In 2014, WIT designed a curriculum and created a transportation patch for the Girl Scouts.[24] They also created a Girl Scout Patch and distributed it to the troops and held the first Girl Scout event, in Chicago, to educate young women about potential careers in the transportation industry.In 2014, the Women In Trucking Association also started a monthly segment on the Dave Nemo Show.

In 2012, Redefining the Road, became the association's official member publication. Its total readership is approximately 15,000.

In 2015, Women In Trucking then established the “Distinguished Woman in Logistics” award sponsored by TMW Systems and also created the WIT Index.[26] It also held the first Accelerate! conference and expo in Dallas, Texas.[27] Mary Aufdemberg also became the new chairwoman of the non-profit in March 2015 after Phyllis Cochran and Foxall.

In 2016, The Women In Trucking Association partnered with the National Transportation Institute for their WIT Index, which quantifies the number of women drivers and management at organizations nationwide. WIT's goal is to increase the percentage of women employed in the trucking industry for which they developed the WIT Index to monitor the percentage of female drivers and leaders within the industry. They partnered again in 2019