Osler participates in the Legal AI Hackathon (Toronto) Osler participates in the Legal AI Hackathon (Toronto)

As artificial intelligence reshapes the legal industry, Osler is at the forefront of this transformation — actively shaping the delivery of legal services smarter, faster and more efficiently. Our commitment to innovation was on full display as we proudly sponsored the inaugural Canadian AI hackathon co-hosted by Queen’s University Conflict Analytics Lab (CAL) and Stanford CodeX.

The Legal AI Hackathon was held at the Smith School of Business in Toronto on February 16, 2025. Despite the heavy snow that hit the Greater Toronto Area during the event, it brought together nearly 200 lawyers and computer scientists/engineers to collaborate in the development of AI solutions that uses OpenJustice — an open-source platform designed to integrate legal reasoning into AI models.

The legal industry is at an inflection point, whereby the adoption of AI tools in legal practices has skyrocketed. According to Clio’s Legal Trends Report, approximately 80% of lawyers have adopted the use of AI tools in some capacity, up from approximately 20% since 2023. This is redefining how legal professionals interact with AI and Osler recognizes the opportunities it creates. As part of Osler’s dedication to legal innovation and AI expertise, our participation in the Hackathon was spearheaded and organized by Natalie Munroe, Chief of Osler Works – Transactional and Legal Operations. This initiative served as a testing ground for new ideas. The event was structured to foster interdisciplinary collaboration between lawyers and technical professionals, with teams of about five people working together to resolve issues by embedding legal knowledge into large language models.

Sam Ip, a partner in the Technology Group at Osler who is focused on advising AI companies and organizations making use of AI, delivered the keynote and participated as a judge on a 10-person panel. He spoke about how, as a leading technology law firm, Osler’s participation underscored its commitment to innovation and its role in AI-driven legal solutions. Sam discussed the changing legal landscape, the significant opportunity to improve how legal services are delivered, the innovator’s dilemma, and why hackathons like this matter.  

Osler solutions

There were two teams with participants from Osler. The first team, the “J.A.R.V.I.S. Wranglers,” included Handi Xu, associate, Emerging and High Growth Companies Group (EHG), Sophie Fu, associate, Technology, Tyler Lovell, legal developer and Sumaya Ali, legal technology coordinator. The project goal was to build a tool to more effectively deploy institutional knowledge to support the SaaS negotiations process. The objectives were to save time spent on searching for precedents and redlining, provide specific responses tailored to the evolution of negotiations, and leverage internal resources. They drew from experiences advising emerging and high-growth companies and negotiating and drafting technology commercial contracting.

The second team, the “Smooth Operations,” included Oren Kedmi, practice support intern, EHG, Carmen Bruni, AI lawyer, and Mary Hum, knowledge systems product architect. They developed a lawyer-client tool named OslerASSIST, which was tailored for early-stage EHG clients. This tool aims to provide the client with tier-one support questions, guidance through basic legal processes, and efficient escalation of complex issues to lawyers. It would optimize and increase the efficiency of lawyer-client communication, deliver significant value to the target audience and increase both lawyer and client satisfaction. They drew from their expertise as part of the Legal Operations team as well as their practice experience.

What’s next

The winning team was “Ace Attorney,” which developed a pro bono intake solution to address the challenge of handling 10,000 weekly calls. Pro bono is close to Osler’s commitment as well. Their solution leveraged LLM-based story mapping, allowing individuals to tell their legal stories their way, rather than being lawyer-led. The tech stack involved OpenJustice and a case law-linked data system integrated into a story database.

Osler’s sponsorship and hands-on involvement in the inaugural Queen’s University Conflict Analytics Lab and Stanford CodeX reaffirms Osler’s ongoing commitment to supporting legal innovation. Osler is at the forefront of change — finding solutions to challenges and helping shape the future of the way we work.

Read more about the LLM x LAW Hackathon.

From left to right: Carmen Bruni, Sumaya Ali, Oren Kedmi, Mary Hum and a member of a non-Osler team.

Sam Ip speaking at the Legal AI Hackathon.