“You can make your job easier with AI. Will you let me help you do that?”
It’s a question you might not expect from a law colleague. But if you’re ever on Jason Barnwell’s (JD 2007) team, you’ll hear it often.
Over 15 years at Microsoft, Barnwell took a leading role bringing AI to legal work — and getting people on board with change. He is now building upon that experience as chief legal officer at Agiloft, a global data-first contract lifecycle management (CLM) software company.
“I want to build the future of our practice because it elevates our work, benefits our clients and expands access,” Barnwell says. “When I wrote software for a custom case citation scraping system for Professor (Dan) Klerman while at Gould, I saw unbounded potential. Back around 2006, the system processed a large volume of very old English cases and built a database of citations Professor Klerman could query — think Westlaw/Lexis but for a very specific application. These fulcrums for human intelligence are becoming easier to make and use every day.”
Barnwell is uniquely positioned at the intersection of law and technology. After earning a mechanical engineering degree from MIT, he spent five years as a software engineer. Then he earned his JD at the USC Gould School of Law and joined Cooley LLP, where he built tools as an associate to support his Emerging Companies and Venture Capital practice.
The biggest challenge with AI, Barnwell has found, isn’t finding the right tools — it’s convincing people to use them. “It’s a sociological challenge masquerading as a technical challenge.”
It helps that his spouse, also a USC alum, is a psychologist. “I have an in-house executive coach who helps me accelerate the change journey.”
Operating at the cutting edge
Barnwell wore many hats in Microsoft’s Corporate, External and Legal Affairs department — starting as a product attorney in the Cloud and AI Platform Business, then leading the Open Source practice. He went on to head the Legal Business Operations and Strategy team before becoming general manager for Digital Transformation. In those roles, he directed investments in culture, processes and tools that delivered technology-powered practices that scale. A year and a half ago, he transitioned into a more conventional practice leadership role as head of legal for Monetization and Business Planning.
At Microsoft, he and his team’s program manager built AI-powered workflow systems that helped his team scale, including the development of a client matter intake system.
“AI support can be easy. We added a robot to email threads and gave it commands — like ‘create a new matter,’” he says. Barnwell likened it to handing off a task to your assistant.
Grounded in law
Amid his wide range of roles, Barnwell sees himself first and foremost as a lawyer. “All these tools are ways I create more leverage on my legal skills. But I don’t create any leverage without strong legal skills.”
“Gould gave me an excellent, practical grounding in how to think, reason and communicate,” he says. “A class that has been incredibly valuable throughout my career was (Professor) Michael Chasalow’s Counseling the Startup. It focused me on first learning what a business cares about to drive outcomes clients value.”
He adds, “Gould, Cooley and Microsoft have taught me so much. Now I have learned how to bring value to Agiloft’s customers by leveraging those amazing experiences. It’s time to build.”
And he’s doing exactly that as chief legal officer.
“We’re rebuilding our workflow systems with AI to augment humans and create self-reinforcing processes,” he says. “This lets people move up the value stack to focus on the more complex parts of our practice. That’s how we will create more value for legal practices within the enterprise.
“AI is very real and it works,” Barnwell says. “To harness AI faster, attorneys must complement our critical thinking with systems thinking. I walked this path. I want to help other people run it.”
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