Legal innovation begins long before technology enters the room, says Rosie Kogan, general counsel and chief legal officer at Medcan in Toronto. “My experience has been that without rethinking the key elements of your foundation, your processes … it becomes very difficult to leverage technology in a way that's productive.”
The conviction comes from a career spent building legal functions in organizations under pressure – 12 years of acquisitive growth at Morneau Shepell and LifeWorks, rebuilding a legal department at GreenShield using fractional counsel, and now a year into Medcan's governance infrastructure for responsible AI adoption in healthcare.
The limits of litigation
After earning her Juris Doctor at Western University and articling at Lerners LLP in Toronto, Kogan was part of the counsel team on Honda Canada Inc. v. Keays – a Supreme Court of Canada case that reshaped the law on punitive damages in employment and the scope of employer obligations around medical accommodation. The case sharpened her interest in employment law – and raised a question she could not let go: how many disputes can be resolved before reaching court?
“I was also really struck at how time-intensive, labour-intensive, resource-intensive it was to resolve disputes … if only things had been different at an early stage, this might have ended up in a way that would have been a better result for both sides,” she says.
Learning through acquisition
Kogan joined Morneau Shepell, expecting to do litigation support work. The role expanded quickly to include employee assistance programs, regulated health professionals, employment law, privacy, and general solicitor's work. “It turned out that I had to learn how to do everything,” she says.
The organization's acquisitive culture pushed her development in ways a static employer could not. Morneau Shepell eventually rebranded as LifeWorks and was acquired by TELUS Health. Kogan built the company's first privacy office from a solo role to a five-person team before the acquisition closed – an experience that has proved increasingly relevant as data privacy tops the list of priorities for general counsel across Canada.
“One of the great things about being in a company that's acquisitive is that there are new businesses, new services, new opportunities that tend to come with acquisition,” she says. After spending years helping absorbed companies find their footing inside Morneau Shepell, she experienced the inversion firsthand. “You go from this career where you're seeing all of this acquisition … and then you have the humbling experience where you're on the other side of the coin,” she says.
Building a team on fractional resources
At GreenShield, Kogan arrived during a period of transition in the legal department and had to rebuild the team while simultaneously learning the organization. Rather than default to law firm secondments, she brought in fractional counsel – former in-house lawyers with expertise in each line of business – to keep legal services running while she evaluated permanent hires.
“[W]e were much better served by having former in-house lawyers who were fractional to be able to keep the team going,” she says. The financial case was clear: fractional support cost significantly less than traditional law-firm billing for day-to-day matters while preserving cultural fit and subject-matter continuity. The legal department tripled in size over two years.
AI governance in healthcare
Now leading what she calls a “small and mighty team” of four at Medcan – herself, a lawyer, a privacy and compliance lead, and a legal operations specialist – Kogan is doing the same foundational work that preceded every successful scaling effort: templates, policies, contracting playbooks, and risk frameworks. Medcan is opening three new locations within a year and needs its legal function to scale accordingly.
“My belief is that until you get the foundation to stabilize in terms of the people, the processes, the policies, the approaches, the consistency, it's difficult to move with speed and on a larger scale because you haven't started from a foundation that essentially … allows you to do that,” she says.
That groundwork is enabling the larger project: a formal AI governance model comprising a data and AI enablement committee, an AI use policy, a responsible use assessment process, and a data governance framework, built to guide Medcan’s adoption of AI to enhance its clinical service delivery. With Canada's AI governance framework still evolving with comprehensive legislation unlikely, Kogan says in-house counsel are now expected to lead this build from scratch rather than simply support it.
“I've seen a lot of projects fail because thought hasn't been given to that foundation,” she says. “There's this assumption that technology is going to come in and solve everything for you … if you don't have the right data, if you don't have the right templates, if you don't have the right risk tolerance established … you're not going to be able to leverage technology in a way that's going to allow you to see the value from it.”
For in-house lawyers seeking a practical starting point, the Association of Corporate Counsel has developed an AI toolkit specifically for in-house legal departments navigating responsible AI adoption. That expanded role – guiding organizations through technological change without a clear legal map – is, she acknowledges, inherently uncomfortable. "It puts people in a place of discomfort that they need to lean into," she says. “It’s also an opportunity to guide an organization during a pivotal moment using the skills lawyers are known for, which is using good judgment to get ahead of potential problems and accelerate growth.”