Caroline Simons



Clients in crisis engage Caroline for high-stakes internal investigations and complex litigation. Because the challenges companies face don't often fit neatly into one area of law, Caroline draws on her broad experience across cybersecurity, criminal law, and IP and commercial disputes to help clients see around corners and manage reputational and business risk, all while furthering their business and organizational objectives. 

Caroline leads the Boston office and uses her extensive litigation and trial experience to help defend clients facing investigations and civil enforcement proceedings. In the realm of cybersecurity and data breach incident response, Caroline helps clients design and conduct large-scale internal investigations, and regularly advises clients and their Boards on security strategy, remediation, and risk mitigation. Caroline also has defended clients--including through trial and appeals--against allegations of fraud, securities violations, public corruption, and Foreign Corrupt Practices Act violations, resulting in favorable negotiated resolutions or decisions not to prosecute. She has conducted internal investigations involving suspected trade secret theft, fraud, financial misconduct, FCPA, and anticompetitive behavior, on behalf of both public institutions and companies of all stages.

Another focus of Caroline’s practice is intellectual property litigation, with a particular emphasis on disputes involving trade secret misappropriation and trademark and trade dress infringement claims. She has handled multiple trials before judges and juries, in state and federal court, and before the International Trade Commission (ITC). In this space, she has represented and defended companies across the tech, life sciences, pharmaceutical, materials, manufacturing and financial sectors.

Caroline currently co-chairs the IP Litigation Committee of the Boston Bar Association's Intellectual Property Law Section. In 2017, Caroline was named an Up & Coming Lawyer by Massachusetts Lawyers Weekly, and has been named a Rising Star by Super Lawyers in 2016 - 2020. She currently serves as co-chair of Orrick's DEI initiative and is an ambassador in the Move the Needle initiative, a trailblazing collaboration between Orrick, Diversity Lab, leading GCs, and four other law firms to advance diversity and inclusion in the legal profession through ambitious goals and bold experimentation. Caroline also maintains an active pro bono practice, currently representing children and refugees in asylum proceedings in conjunction with the Political Asylum / Immigration Representation (PAIR) Project. She has drafted amicus briefs in cases pending before the U.S. Supreme Court and U.S. Circuit Courts of Appeals in the areas of federal sentencing guidelines, reproductive rights, and political law.  

    • Conducted internal investigation on behalf of leading education technology company to assess its incident response processes.
    • Conducted multiple data breach internal investigations for leading higher educational and research institution.
    • Obtained favorable International Trade Commission determination in modification proceeding on behalf of Mahindra & Mahindra Ltd. and Mahindra Automotive North America in trademark and trade dress litigation; continuing to represent clients in parallel federal district court proceedings.
    • Representing leading online grocer in copyright and CFAA litigation against competitor regarding allegations of data-scraping images from consumer-facing website. 
    • Defended education technology company and former employees against allegations of trade secrets misappropriation. Settled favorably before preliminary injunction hearing after conducting swift forensic investigation.
    • Represented leading materials company Teknor Apex in defending against allegations of trade secrets misappropriation following failed joint venture. Settled favorably following the first, key 30(b)(6) deposition of adversary.
    • Obtained acquittal for client charged with attempted Hobbs Act extortion after a 7-day trial.
    • Represented emerging life sciences company in ultra-rare disease space in suit alleging trade secret misappropriation.
    • Represented and counseled life sciences company in responding to pre-suit allegations of trade secret misappropriation levied by competitor arising out of departure of consultants and work with co-founders. 
    • Successfully represented attorneys under federal investigation for conspiracy to defraud the United States; U.S. Attorney’s Office declined to prosecute.
    • Represented drone technology company in investigation and dispute with departing engineer with respect to trade secret misappropriation.

    • Counseled sports technology company with respect to suspected trade secret misappropriation and copyright violations stemming from failed joint venture.

    • Counseled and conducted investigation for search engine companies with respect to suspected trade secret misappropriation and Computer Fraud and Abuse Act violations by former partner. 

    • Counseled start-up client focusing on battery technology with respect to policies protecting proprietary information and trade secrets.

    • Represented a manufacturer of solar panels in an offensive trade secret misappropriation case brought under Mass. Gen. Laws ch. 93A, obtaining judgment awarding treble damages under a lost profits theory and attorney’s fees, permanent injunction, and a 5-year production injunction. Judgment upheld in full by the Massachusetts Appeals Court.
    • Conducted an internal investigation on behalf of a state university regarding misuse of public funds by its President, leading to his resignation. Attorney General's Office subsequently filed suit against the individual to recover state funds.
    • Successfully represented members of the state legislature in federal investigation prosecution involving charges of bribery.
    • Conducted an internal investigation on behalf of a private health and beauty care company regarding allegations of anticompetitive conduct.
    • Represented hedge fund in shareholder dispute regarding voting rights, successfully obtained summary judgment and injunctive relief that was upheld by the Massachusetts Supreme Judicial Court.
    • Represented semiconductor company in patent litigation appeal involving allegations of spoliation; successfully obtained affirmance in the Federal Circuit Court of Appeals.