In the same year, he received Doctorate of Philosophy in computer science from Indian Institute of Technology, Delhi for his PhD research performed at MIT.

From 1979 to 2004, Gupta served as the founding co-director of the Productivity from Information Technology (PROFIT) Initiative and an allied roles at MIT Sloan School of Management.

As Diversity Committee Member for three terms, each 3 years long, he assisted in increasing the number of underrepresented minorities at Sloan.

He led a UNDP team to plan and implement a national financial information infrastructure in a Latin American country where 40 percent of the banks had gone bankrupt.

In this position, in cooperation with Professor Lester Thurow (former dean of MIT Sloan School of Management), he launched the United States' first course on international outsourcing.

Gupta played a significant role in creating the vision for new interdisciplinary research initiatives, such as the proposed multi-college endeavor that would enable United States and Mexico to enhance healthcare in bordering areas through mutual cooperation without investing any additional funds.

As the Founder and Head of the "Nexus of Entrepreneurship and Technology" initiative, Gupta interacted with the trustees of the Thomas R. Brown Foundation to delineate and refine ideas that are of high interest to the individuals who have sponsored the endowed chair.

One of the projects, The Telehealth Intervention Program for Seniors (TIPS), was selected for a National Association of Counties (NACo) Achievement Award in 2016.

Gupta proposed new national policy on telemedicine, which became fully effective on June 11, 2018, by the US Department of Veterans Administration (VA).

Mooted this model in 2001 for improved interpretation of mammograms using on-site technicians, off-site radiologists, and emerging data mining technology.

The first project was published in a special issue of Machine Learning and Knowledge Extraction and received press by the MIT News and The Boston Globe.