Encouraging a more sustainable commuter mode shift and improving urban transportation systems have the potential to reduce anthropogenic greenhouse gas emissions (GHGs), a major contributor to climate change. Replacing some single-occupancy vehicle (SOV) trips with alternative modes of transportation, such as public transit, walking, or bicycling, represents one approach to begin reducing transportation-related emissions. Collectively, these shifts in transportation patterns would help to reduce the negative social, economic, and environmental costs associated with high rates of personal vehicle use. Employer-provided benefits programs have the potential to influence commuter behavior by making sustainable, alternative commuting choices a more convenient and economically feasible option. In addition, the implementation of these programs can have broader benefits such as helping to achieve municipal and regional sustainability goals and improving community members’ physical health and quality of life. This study applies qualitative and quantitative analysis to investigate employee commuting behavior in response to employer-provided benefits in Kendall Square, a neighborhood in Cambridge, Massachusetts. The employee and employer survey data analyzed in this research was originally collected by TransAction, a transportation consulting firm in the Greater Boston region. To comply with Cambridge’s Parking and Transportation Demand Management (PTDM) Ordinance, TransAction works closely with companies to coordinate and manage onsite commuter services programs and prepare PTDM Annual Reports. The primary objectives of this research are: 1) to introduce the multi-dimensional benefits of re-envisioning the existing transportation networks; 2) to determine the influence of employer-provided commuting benefits on employee commute mode choice; 2) to provide guidance for employers interested in promoting a more sustainable employee commute mode split; and 3) to present the broader implications and applications of this research for employers, municipalities, and coordinating agencies interested in reducing SOV commuting trips and promoting the use of more sustainable, alternative modes of transportation. Overall, the findings from this research illustrate that while employers have the ability to promote more sustainable transportation choices among their employees, the complexity of the transportation network (and its interdependencies) requires collaboration among all stakeholders to initiate widespread, comprehensive changes.