Artificial intelligence has transformed the way the world works in a very short period of time. Naturally, this rapid adoption has many lawyers in particular worried they’ll become irrelevant within a few years. James “Jimmy” Toy took a different approach to AI anxiety. He decided to lean into it. If his CLO role is someday replaced by AI, what might that free him up to do instead?
“I kind of turned the 'oh no, we're gonna get replaced' mindset on its head and said: replace me. How can I be replaced?" Jimmy asks.
Jimmy is currently the Chief Legal Officer at Articore Group, the parent company of Redbubble and TeePublic, two of the largest online marketplaces for independent artists in the world. The platform processes millions of user-generated images, and consequently, Jimmy’s legal team has handled nearly 50 IP cases in 12 years. That relentless workload honed Articore’s legal team into one of the most capable in-house IP litigation teams of any marketplace company.
“I like to say we win most of them, but we don't win them all,” said Jimmy. “And I think that's actually a very important observation for risk management. I think if we won all of them, we might be managing risk with too heavy a hand.”
Why Lawyers Are Uniquely Resistant to AI (and How to Fix It)
Jimmy believes that the legal field’s deep discomfort with AI comes down to identity. There is a deep-seated belief that exercising independent judgment, backed by demonstrable time and effort, is what makes a lawyer valuable. Then the billable hour turned that belief into a business model.
Going in-house changes the metric from hours to output, but that identity tends to stick around. This has resulted in a world of legal professionals who are structurally incentivized to resist the one tool most likely to help them scale.
"As a lawyer, you feel like you're responsible for everything, every output, every response,” said Jimmy. “It does make it harder to embrace a new tool that is new and risky and uncertain, but has such potential to transform the way we do our work."
Jimmy has found success in helping each of his employees identify areas of their workflow that don’t require a lawyer. After they automate one repetitive task, they begin to reframe AI as a transformational tool rather than a replacement. The value of a lawyer lies in the judgement and wisdom they offer that an algorithm cannot.
"If you're in-house, you want to build trust with your fellow executives,” Jimmy said. “You want to show you're the person they can come to that has the answers. They could have gone to the LLM and gotten 80% of the answer I gave. What lives in that 20%?"
What Twelve Years of Litigation Teaches a Lawyer About Risk
Jimmy joined Redbubble in 2014 as a generalist corporate lawyer. At the time, the company had never been sued. Within six months Jimmy was managing his first IP case. Twelve years later, the company has been acquired and Jimmy’s team has worked through fifty UP cases across the United States, Australia, Europe, and Asia. The case that sticks with Jimmy the most was a decade-long trademark dispute brought by the Hells Angels that went to federal court, was appealed, and ultimately influenced a new trademark law in Australia.
The case shined a light on a gap in Australian law. The US had the DMCA; the EU and India had their own frameworks. Australia had safe harbor protection for copyright but nothing comparable for trademark infringement on user-generated content platforms.
The Hells Angels sued because someone was selling unauthorized apparel with Hells Angels’ logo. Articore lost the first round, but they kept fighting and eventually won. It was Jimmy’s decision to appeal, and that’s the kind of judgment call that can’t be made by an AI tool.
"I think I testified against the Hells Angels in federal court because it was a trademark case,” recalls Jimmy. “The case went on for 10 years. We just in the last couple of years won on appeal. I'm very proud of it because it actually created a law in Australia, similar to what the United States has, which helps all platforms operating in Australia.”
The broader lesson Jimmy learned from twelve years of multi-jurisdictional litigation is that risk management is not about winning everything. It is about managing the portfolio of cases in a way that reflects the company's actual risk tolerance: not too aggressive, but not too defensive. A clean sweep would mean you are leaving value on the table somewhere.
How AI Can Help Create Consistency Across Jurisdictions
Over nearly fifty IP cases, Articore has made thousands of arguments, filed hundreds of briefs, and described their platform and business model in countless ways for countless courts. The risk of contradiction in different jurisdictions was previously reliant on Jimmy’s memory alone. He’d be the first to tell you this was not a sustainable or scalable solution for any company, let alone one the size of Articore.
Jimmy used AI to create a novel solution: a knowledge base created from every court filing, deposition transcript, affidavit, and declaration the company has produced. The whole archive went into the LLM’s folder, and now Jimmy’s team can now interact with the knowledge base as if it were a person. They can ask questions about previous arguments the company has made and whether they’ve ever made an argument that might conflict with a current argument.
"It would fall on me to make sure everything was consistent,” Jimmy laughs. “I might spend three hours trying to figure that out and maybe not come to an actual answer. Now I can just not even do that. I can farm it out to the AI tool and I don't have to do it anymore."
The best part of the new system is that AI is comprehensive in a way human memory can’t be. Jimmy may have forgotten a specific passage in a deposition seven years ago, but the legal AI has not. A knowledge base never gets tired, never forgets a fact, and works even without the CLO in the room.
"You would never look at a deposition transcript or look for something in your briefs, but here you can put it all in and create this excellent knowledge base that's comprehensive,” said Jimmy. “And then you can just interact with it like it's a person."
No Surprises: Building a Legal Team Led by Values
Articore has been through growth phases, contraction, and is now in a turnaround phase. Regardless of the wave they are riding, Jimmy’s team operates by three core values:
Light Touch
No Surprises
Make Every Dollar Count
Of the three, “No Surprises” has the most universal application regardless of where a company is in a growth cycle. than the legal team. The job is not to control every risk. It is to make sure the people who need to know are informed in time to ask the right questions.
"Light touch, no surprises, make every dollar count,” repeats Jimm. “We keep trying to add things to that list of three, but everything keeps going back to it."
The Case for Building a Legal Function That Works Without You
Jimmy suspects there are many other companies with legal functions that rely solely on the GC for vital institutional memory. AI is how these legal leaders begin to decentralize their knowledge to people on their team.
“I envision being able to create self-help tools for people on other teams to replace you as the person they had to ask before and wait for. It's a lot cheaper for the company and a lot faster,” he said. “It’s very, very beneficial to our profession, and to really delegate things that before, only you could do.”
The idea of replacing oneself has been shared before on CZ and Friends, most recently by Rachel Harris who built a markdown file to “hand her brain to engineering.”
Using AI to delegate and extend your capacity will not lead to a lawyer’s irrelevance. The right legal AI tools can help you take control of your time, so you can focus on the 20% that only you can do.
AI will never replace the judgment calls that require twelve years of experience in courtrooms and a deep understanding of the business, or the decisions like appealing a case that no knowledge base can confidently make.
That is where the value of AI is, and getting there requires building the systems, and tools to allow your team to thrive in this new world. GC AI is a legal tool created for high-functioning legal teams that want to build faster. Try it for free at gc.ai.
