Robert M. Weiss


Rob provides strategic legal and business advice on a variety of commercial information technology matters and complex technology transactions that impact his clients’ operations worldwide, including cloud and machine learning agreements, systems integrations, infrastructure and business process sourcings, technology development and data licensing projects,  data center and co-location agreements, and telecommunications procurements.

Rob’s client base is focused on assorted businesses having sophisticated technology needs spanning a broad spectrum of industries, including financial services, health care, hospitality, private equity firms, transportation and logistics, and credit card processing. He regularly assists clients in taking advantage of the numerous benefits of operating in the cloud, and he also develops and implements strategies for navigating the constantly evolving challenges of data privacy best practices and compliance. Clients appreciate his talent for managing the distinctive dynamics of relationships between companies during and after technology transaction negotiations.

Rob has practiced exclusively in the area of information technology law for two decades. He is a recognized leader in the community of technology law practitioners, currently serving as President of the ITechLaw Board of Directors. He regularly speaks and writes on subjects associated with information technology. In 2018 he appeared on the China Global Television Network (CGTN) in a segment about the telecom industry. Rob has published articles and been quoted in a variety of newspapers, journals and other media outlets, including the Los Angeles Times, CNN Money, Consumer Reports, CFOMagazine, Computerworld, Real Simple, the Journal of Internet Law, the University of Virginia Journal of Law and Technology, and the Health Information Privacy/Security Alert.

Professional Affiliations:

  • President of the ITechLaw board of directors (2017-present)
  • Member of the Executive Committee of ITechLaw Association (2013-present)
  • Elected to the ITechLaw board of directors for (2007-2013)
  • Selected as one of America’s Leading Lawyers for Business in Technology & Outsourcing by Chambers USA (2006-present)
  • Selected as one of the “40 under 40” outstanding Illinois attorneys by Chicago Daily Law Bulletin (2003)
  • ITechLaw Association, Sponsorship Chair (2008-Present), and U.S. Developments editor of ITechLaw’s principal publication, The Bulletin (2001-2006)
  • Chicago Bar Association, Computer Law Committee, chairman (2002-2004)
  • Counsel to client in outsourcing of performance management for client’s IT infrastructures.
  • Counsel to payment solution systems client in outsourcing of software development.
  • Counsel to software development company on application development agreement and license.

Bar Admissions

  • Illinois