Hillard M. Sterling

Practice Areas:

Cyber Law, Technology Law, Professional Liability, Employment and Labor, Commercial and Business Litigation, Directors and Officers, Intellectual Property, Insurance Coverage
Office Location: Illinois
Tel: (312) 985-5600 Fax: (312) 985-5601


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Hillard M. Sterling is Managing Partner of Winget, Spadafora & Schwartzberg, LLP's Chicago office. Mr. Sterling's practice focuses on technology and cyber disputes and issues, bringing 25 years of experience in the entire range of technology cases, such as disputes related to systems implementation, software development and licensing, and IT intellectual property. Mr. Sterling also regularly represents a broad array of professionals in litigation, including attorneys, architects & engineers, accountants, agents and brokers, and real-estate professionals, among others, as well as directors & officers in a variety of business disputes.

Mr. Sterling counsels clients on developing and implementing best practices before, during, and after data breaches and incidents. Since strong preventive measures are central to reducing exposure and damages, Mr. Sterling works with clients to: (1) develop or improve policies, incident-response plans, and data-governance plans; (2) develop or improve employee training procedures and techniques; (3) develop or improve table-top exercises; and (4) comply with governing law and stay current with the latest cyber-law developments. The underlying objective of all of these measures is to help clients establish a cyber-security corporate culture.

Mr. Sterling also represents clients in defending against national class-action lawsuits based on alleged disclosures of information allegedly protected by federal and state statutes. These cases typically are the subject of dispositive motion practice based on standing and other grounds, and Mr. Sterling is versed - and speaks frequently before various audiences - on the developing jurisprudence under which these cases may be resolved successfully and expeditiously.

In addition, Mr. Sterling assists insureds and other clients as a "breach coach" to coordinate and quarterback responses to data breaches or incidents. In this role, Mr. Sterling helps guide and manage the many responsive tasks, including analyzing the nature and scope of the breach or incident, assessing the legal implications and developing and implementing strategies based on those implications, implementing incident-response plans, and communicating internally and externally with the many pertinent constituencies, all while utilizing and maximizing the confidentiality protections of the attorney-client communication privilege where feasible.

Mr. Sterling's practice encompasses many other types of commercial matters, including shareholder and partner disputes, intellectual property, employment, securities, antitrust, the False Claims Act, and products liability.

Mr. Sterling has served as an expert commentator in print and broadcast media, and regularly speaks and presents, on various technology topics.

Mr. Sterling received his J.D. in 1989, magna cum laude, and Order of the Coif, from Georgetown University Law Center, where he was an Executive Editor of its flagship law review, the Georgetown Law Journal. Mr. Sterling is a 1986 graduate of Northern Illinois University, where he received his B.A., summa cum laude.

Mr. Sterling is admitted to practice law in Illinois and Washington, D.C., and various federal courts including the trial bar of the Northern District of Illinois.

Representative Matters

  • Defended website developer against allegations of breaches of contract, unfair trade practices and other alleged misconduct during the course of developing a new website for the launch of a children's hospital. Reached favorable settlement after written discovery and before proceeding with multiple depositions.
  • Defended case filed by aggrieved customer complaining about the functionality of a software tool developed for an Internet music-marketing platform. Reached favorable settlement involving nominal transfer after asserting counterclaims and exposing vulnerabilities in early discovery.
  • Defended vendor of wireless access points in litigation filed by a school district which alleged breaches of contract and violations of warranties during the project. Reached favorable settlement after asserting counterclaims and highlighting weaknesses given the express contractual terms.
  • Defended a national healthcare-system vendor in litigation involving a project to implement an integrated clinical-information system at a large healthcare network. Secured successful settlement on the brink of verdict following twenty-one trial days.
  • Retained by an insurer as defense counsel in connection with a $200 million claim for alleged damages caused by failures to implement a functional software system. Asserted counterclaims and secured a settlement representing approximately 1% of insured's claim.
  • Defended majority shareholder, sole director, and president of national provider of commercial scaffolding against multiple individual and derivative claims for breaches of fiduciary duties and other alleged misconduct during the course of managing and operating the company over a six-year timeframe. After defeating plaintiff's summary-judgment motion on his claims and proceeding through a week-long bench trial, secured successful judgment finding no liability on all pending claims and holding that the alleged misconduct was protected by the business-judgment rule.
  • Defended director and president against claims by shareholders alleging breaches of fiduciary duties, securities violations and other alleged misconduct in connection with the operation and management of a public company selling vitamin-infused spices. Reached successful resolution in settlement after prevailing against plaintiffs during the course of pleadings motion practice.
  • Defended sole officer and his investment company against allegations of misconduct in connection with the transfer of publicly traded stock. Secured successful judgment after bench trial finding no liability.
  • Represented insureds and other clients in a variety of labor and employment matters, including disputes in federal and state courts involving claims for breaches of contract and statutory claims under the Illinois Wage Payment and Collections Act.
  • Represented insureds and other clients in actions alleging the breach and enforceability of non-competition and non-solicitation restrictions.
  • Represented insureds and other clients in actions alleging the breach of payment and benefits contractual terms and conditions.
  • Defended insured in claims alleging patent infringement and other alleged misconduct in connection with software developed to search websites and process Internet sales. Settled early in the litigation for a small fraction of the alleged damages.
  • Defended insured against claims alleging trademark infringement in connection with the sale of spices, fruits and nuts. Resolved the case successfully through an early settlement involving no monetary transfer.
  • Defended insured against claims alleging trademark infringement and unfair competition based on alleged similarity in the names of competing Italian restaurants. Resolved the case successfully through an early settlement involving no monetary transfer.