Caroline Simons



New York

Caroline Simons is a litigator and trial lawyer who defends technology companies in disputes involving data, online safety, and intellectual property. Her interdisciplinary experience enables her to problem-solve and guide her clients through crises, defend them in high-stakes litigation, and manage enterprise risk strategically, effectively, and efficiently.

Caroline represents tech and consumer-facing clients -- from early-stage startups to some of the most recognizable online companies -- in litigation to protect their IP, brand, and reputation. Caroline's expertise includes the fast-evolving areas of Section 230 of the Communications Decency Act and online safety, cybersecurity & data privacy litigation, and IP litigation, including trademark/trade dress infringement and trade secret misappropriation. She is lead counsel in dozens of cases for one of the world's largest tech companies on claims challenging its content moderation and product design. Caroline also has advised clients in cyber incident response, including crisis management, government and internal investigations, and enforcement. Her experience gives her breadth of perspective and allows her to work with her clients to make swift and pragmatic decisions to effectively manage their reputational, legal, and financial risks. Clients appreciate Caroline's ability to engage, listen to, and connect with witnesses, company stakeholders, and factfinders -- both inside and outside the courtroom -- to achieve meaningful results.

  • Caroline was named an Up & Coming Lawyer by Massachusetts Lawyers Weekly in 2017, and has been recognized by Super Lawyers from 2016 - 2022. Caroline maintains an active pro bono practice, representing clients in Hague proceedings as well as 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 technology, criminal justice, and reproductive rights.

    • Representing leading technology company in cases involving challenges to its content moderation practices, product design, online safety, and Terms of Service/Terms of Use. 
    • Representing companies in tech, retail, fintech, and hospitality in data privacy cases arising from use of pixels, session replay, and chatbots on consumer-facing websites.
    • Representing companies in the tech and gaming spaces in data breach class action suits.
    • Represented financial services company in successive security breaches implicating vendor controls.
    • Represented travel and transportation company in network intrusion.
    • Represented leading education technology company and conducted incident post-mortem investigation to assess and develop operational resiliency.
    • Represented 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.
    • Represented Mahindra & Mahindra Ltd. and Mahindra Automotive North America at trial in trademark and trade dress litigation proceeding in parallel before International Trade Commission and federal district court.
    • Represented client charged with attempted Hobbs Act extortion at trial; obtained acquittal after 1.5 hour jury deliberation.
    • Represented emerging life sciences company in ultra-rare disease space in suit alleging trade secret misappropriation.
    • Successfully represented attorneys under federal investigation for conspiracy to defraud the United States; USAO 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.
    • Represented 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 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.