Hillard M. Sterling

Shareholder
Chicago
70 West Madison Street
Suite 3000
Chicago, IL 60602
P 312.962.8082
F 312.580.1201
P 312.962.8082 | F 312.580.1201



Overview

Hillard is a commercial litigator and trial lawyer with thirty years of experience bringing cases to successful resolutions through settlement, judgment, and verdict in tribunals across the country. He brings a strategic, creative, and focused approach to his clients’ cases and disputes, and a wealth of litigation and trial experience at firms ranging from big law to boutique.

Hillard’s matters span the spectrum of commercial and insurance defense matters, including professional liability cases (defending agents, brokers, and financial advisors), technology system implementation disputes (representing vendors and customers), cyber matters (breach coaching and counseling clients on risk reduction), privacy cases (defending clients against allegations of wrongful disclosures and access), defamation claims (defending and bringing claims on behalf of private and public figures), intellectual property (defending against infringement allegations), and a panoply of other business disputes representing companies, shareholders, and LLC members.

Hillard has served as an expert commentator in print and broadcast media on breaking stories in the technology-law realm. He also speaks at conferences across the country regarding a wide range of technology and cyber issues as well as other insurance-defense topics.

Experience
  • Defending a regional healthcare network against a lawsuit field in Cook County Circuit Court following a data breach involving over 75,000 patient records
  • Defending a software developer against claims alleged by a Canadian airline based on an alleged data breach
  • Defending a manufacturer against a lawsuit filed in Cook County Circuit Court based on alleged violations of the Illinois Biometric Information Privacy Act (BIPA)
  • Defending an industrial machinery supplier against a lawsuit filed in Wisconsin state court based on a wire-fraud scheme in which plaintiff was tricked into wiring substantial funds to a third-party hacker
  • Representing a technology entrepreneur in a lawsuit filed in the United States District Court for the Northern District of Illinois in connection with a failed yet potentially lucrative start-up company
  • Representing multiple insureds in developing and implementing cybersecurity best practices in order to establish strong legal foundations against prospective lawsuits or regulatory investigations alleging deficient protective measures
  • Representing multiple insureds in strengthening their software development and implementation contracts in order to enhance protections involving limited warranties, exclusive remedies, damages limitations, and alternative-dispute-resolution provisions
  • Defended a developer of home-healthcare software against a lawsuit in Minnesota federal court based on alleged software defects and negotiated a favorable settlement following the filing of summary-judgment motions
  • Defended a marketing company against claims alleging misappropriations of client information by a now-former employee and negotiated a favorable settlement prior to discovery
  • Defended a 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 and reached favorable settlement after written discovery and before proceeding with multiple depositions
  • Defended a software-implementation consultant against an arbitration proceeding filed by a national real-estate brokerage based on alleged failures and defects involving an Oracle software system and negotiated a favorable settlement following focused discovery
  • Defended a Microsoft software vendor against fraud and breach-of-contract claims asserted by various customers, including a national mortgage company which retained the client to implement the system at hundreds of sites and negotiated settlements early in the litigation  
  • Defended litigation filed by aggrieved customer complaining about the functionality of a software tool developed for an Internet music-marketing platform and 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 and 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 and secured successful settlement on the brink of verdict following twenty-one trial days
  • Defended a realtors association in an arbitration proceeding against a large vendor of business-software systems and secured a damages award including attorneys’ fees and costs
  • Defended a home-furnishing seller in an action against a national vendor of information-management systems, prevailing against dismissal and summary-judgment motions, and secured a successful settlement
  • Defended a national hotel chain in an action against a developer of registration software and helped the client secure a successful settlement after aggressive and focused discovery efforts and pretrial-motion practice
  • Retained by an insurer as defense counsel under a professional-liability policy 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
  • Represented an international construction and engineering firm in a lawsuit against its outsourcing vendor based on failures to perform and provide promised products and services, secured continued performance by the outsourcer, and negotiated an expedited wind-down arrangement and transition to a new vendor
  • Represented a customer of outsourced data-processing services in an arbitration proceeding seeking damages and reduced rates over the remaining contract term because of deficient performance by the vendor and secured arbitration award providing all requested relief as well as attorneys’ fees and costs
  • Represented a county government in a dispute against its outsourcing firm based on failures to meet contractually guaranteed service levels and assisted in the negotiation of a new and stronger contract enabling the parties to continue their work together
Services

Education

  1. Georgetown University Law Center, J.D.
    • magna cum laude
    • Order of the Coif
  2. Northern Illinois University, B.A.
    • summa cum laude

Credentials

Bar Admissions
  1. Illinois
  2. District of Columbia
Court Admissions
  1. U.S. District Court, Northern District of Illinois (Trial Bar)
  2. U.S. District Court, Eastern District of Michigan

Affiliations

Professional Affiliations
  • Defense Research Institute

Insights

Overview

Hillard is a commercial litigator and trial lawyer with thirty years of experience bringing cases to successful resolutions through settlement, judgment, and verdict in tribunals across the country. He brings a strategic, creative, and focused approach to his clients’ cases and disputes, and a wealth of litigation and trial experience at firms ranging from big law to boutique.

Hillard’s matters span the spectrum of commercial and insurance defense matters, including professional liability cases (defending agents, brokers, and financial advisors), technology system implementation disputes (representing vendors and customers), cyber matters (breach coaching and counseling clients on risk reduction), privacy cases (defending clients against allegations of wrongful disclosures and access), defamation claims (defending and bringing claims on behalf of private and public figures), intellectual property (defending against infringement allegations), and a panoply of other business disputes representing companies, shareholders, and LLC members.

Hillard has served as an expert commentator in print and broadcast media on breaking stories in the technology-law realm. He also speaks at conferences across the country regarding a wide range of technology and cyber issues as well as other insurance-defense topics.

Experience
  • Defending a regional healthcare network against a lawsuit field in Cook County Circuit Court following a data breach involving over 75,000 patient records
  • Defending a software developer against claims alleged by a Canadian airline based on an alleged data breach
  • Defending a manufacturer against a lawsuit filed in Cook County Circuit Court based on alleged violations of the Illinois Biometric Information Privacy Act (BIPA)
  • Defending an industrial machinery supplier against a lawsuit filed in Wisconsin state court based on a wire-fraud scheme in which plaintiff was tricked into wiring substantial funds to a third-party hacker
  • Representing a technology entrepreneur in a lawsuit filed in the United States District Court for the Northern District of Illinois in connection with a failed yet potentially lucrative start-up company
  • Representing multiple insureds in developing and implementing cybersecurity best practices in order to establish strong legal foundations against prospective lawsuits or regulatory investigations alleging deficient protective measures
  • Representing multiple insureds in strengthening their software development and implementation contracts in order to enhance protections involving limited warranties, exclusive remedies, damages limitations, and alternative-dispute-resolution provisions
  • Defended a developer of home-healthcare software against a lawsuit in Minnesota federal court based on alleged software defects and negotiated a favorable settlement following the filing of summary-judgment motions
  • Defended a marketing company against claims alleging misappropriations of client information by a now-former employee and negotiated a favorable settlement prior to discovery
  • Defended a 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 and reached favorable settlement after written discovery and before proceeding with multiple depositions
  • Defended a software-implementation consultant against an arbitration proceeding filed by a national real-estate brokerage based on alleged failures and defects involving an Oracle software system and negotiated a favorable settlement following focused discovery
  • Defended a Microsoft software vendor against fraud and breach-of-contract claims asserted by various customers, including a national mortgage company which retained the client to implement the system at hundreds of sites and negotiated settlements early in the litigation  
  • Defended litigation filed by aggrieved customer complaining about the functionality of a software tool developed for an Internet music-marketing platform and 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 and 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 and secured successful settlement on the brink of verdict following twenty-one trial days
  • Defended a realtors association in an arbitration proceeding against a large vendor of business-software systems and secured a damages award including attorneys’ fees and costs
  • Defended a home-furnishing seller in an action against a national vendor of information-management systems, prevailing against dismissal and summary-judgment motions, and secured a successful settlement
  • Defended a national hotel chain in an action against a developer of registration software and helped the client secure a successful settlement after aggressive and focused discovery efforts and pretrial-motion practice
  • Retained by an insurer as defense counsel under a professional-liability policy 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
  • Represented an international construction and engineering firm in a lawsuit against its outsourcing vendor based on failures to perform and provide promised products and services, secured continued performance by the outsourcer, and negotiated an expedited wind-down arrangement and transition to a new vendor
  • Represented a customer of outsourced data-processing services in an arbitration proceeding seeking damages and reduced rates over the remaining contract term because of deficient performance by the vendor and secured arbitration award providing all requested relief as well as attorneys’ fees and costs
  • Represented a county government in a dispute against its outsourcing firm based on failures to meet contractually guaranteed service levels and assisted in the negotiation of a new and stronger contract enabling the parties to continue their work together

Education

  1. Georgetown University Law Center, J.D.
    • magna cum laude
    • Order of the Coif
  2. Northern Illinois University, B.A.
    • summa cum laude

Credentials

Bar Admissions
  1. Illinois
  2. District of Columbia
Court Admissions
  1. U.S. District Court, Northern District of Illinois (Trial Bar)
  2. U.S. District Court, Eastern District of Michigan

Affiliations

Professional Affiliations
  • Defense Research Institute