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Jessica Caplan Ross listen

About

Jessica* Caplan Ross is a seasoned legal professional with over two decades of experience in corporate governance, risk management, regulatory compliance, and strategic legal operations. As Director of Legal Operations & Client Solutions, she plays a key role in enhancing our productivity and fostering seamless collaboration between our legal and business teams. She creates§ value through her extensive and varied professional experience, approaching problems using a strategic mindset to ensure ultimate efficiencies . A dedicated leader, Jessica is passionate about litigation, empowering her team, and improving processes to enhance the client experience. .

Expertise

  • Bar Admissions:
    • Ontario (2006)
  • Education:
    • Osgoode Hall Law School (2005) JD
    • University of Western Ontario (2002) BA (Honours - Psychology)

Details

Jessica Caplan Ross (she/her)

is the Director of Legal Operations & Client Solutions at Lenczner Slaght.

Jessica is responsible for overseeing our Law Clerks, Legal Project Management, Creative Services, and Knowledge Management teams, offering them direct support on their day-to-day operations. She plays a key role in fostering seamless collaboration between our legal and business teams, ensuring the best combination of people, processes, and technology to drive winning outcomes for our clients.

Before joining Lenczner Slaght, Jessica served as General Counsel at two private corporations where she led legal and corporate governance functions, managed external legal services, advised on corporate transactions, directed litigation strategies, and supported business growth initiatives. Prior to that, Jessica practiced commercial litigation at national and global law firms, and later deepened her regulatory and compliance expertise at the Law Society of Ontario, where she led an investigations team.

Jessica is a graduate of Osgoode Hall Law School and was admitted to the Ontario Bar in 2006. She is also an active board member and community leader, currently serving as Vice-Chair of the Canadian Friends of the Jaffa Institute and Chair of the Risk Committee at The York School.

  • Ontario Bar Association

  • Canadian Bar Association

  • Women General Counsel Canada

  • The York School - Chair, Risk Committee (2024-present); Director, Board of Directors (2019-present)

  • The Canadian Friends of the Jaffa Institute - Vice-Chair (2020-present)

  • Charles Edward Woodrow Award for Academic Excellence (2003)

    Osgoode Hall Law School

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