In this paper the issues faced by firms in today’s telecommunications environment are compared and contrasted with an actual telecommuting case study of Trade Reporting and Data Exchange, Inc. (T.R.A.D.E.), a software engineering company located in San Mateo, CA. Initial results indicate that telecommuting was successful for T.R.A.D.E because the required technology was widely available (the candidate initiated the idea and had the necessary industry and company experience) the organization could provide the flexible work arrangement while retaining a valuable employee, the employees were able to live in a geographic area of their choice, overall costs could be shared by the company and employees, the job category was an ideal fit, and existing procedures were in place for communicating and managing the geographically detached worker. As telecommunications technology evolves this arrangement will continue to challenge the firm and their employees.