Transitioning from professional civil service, Bennett continued in the professional information technologies field, assisting clients with both new technology implementation and remedial, legacy system management. During this time, he assisted various clients with implementation testing and compliance audits, including ensuring forensic quality standards of presentation persuant to a Sarbanes-Oxley compliance audit. Further experiences included operating, monitoring, and upgrading a Risk & Compliance system to ensure Federal regulatory compliance requirements were met and maintained. Bennett's experiences in these environments gave him extensive knowledge of access and security methodologies, including numerous data encryption techniques.

Beyond his main professional experiences, Bennett as also been a volunteer for a nonprofit educational organization, organizing and coordinating activities of up to a thousand technically oriented volunteers, making special, occasional presentations to schools, professional conferences, and other public groups.

Continuing his civic services, Bennett Rutledge has served as an election judge, as Treasurer for the Libertarian Party of Arapahoe County, Colorado, and filing a Protest of Election (21CV268) protesting a choiceless Election. Bennett also ran for the Centennial City Council (District 2), leading a campaign committee of eight independent thinkers.

Although not elected, Bennett did gather enough votes to achieve "spoiler" position and unseated an incumbent with a far larger war chest. As a firm believer in the power of the People to rationally govern themselves and their leadership, Bennett had the following to say regarding the outcome:

"Starting in 2018, the Centennial City Council has a fresh voice speaking for the people of Centennial ... even if it is not my own!"