MAICON brings together top visionaries and experts in the field of AI during a three-day conference packed with actionable sessions and networking events—all to position you as the change agent your organization (and career) needs. In this ongoing speaker series, we’re featuring these extraordinary leaders, with forward-looking predictions, actionable tips you can use today, and a preview of their MAICON 2025 sessions.
Jen Leonard is the Founder & Principal of Creative Lawyers, a company that develops educational content for leaders in legal who shape creative solutions that respond to change.
Before launching her firm, Jen spent a decade practicing law, first as a law firm litigator, then as Chief of Staff to the City of Philadelphia Law Department. She later returned to her alma mater, Penn Carey Law, where she became its first Chief Innovation Officer and taught courses,including Design Thinking for Lawyers, Law Firm Business Models, and Generative AI in Law Practice.
“Law is an industry that is very slow to change,” she explained. “I kept seeing this huge gap between the pace of technological and societal change and how legal professionals were adapting.”
In 2023, she left academia to establish Creative Lawyers, initially helping firms and legal departments build innovative cultures and navigate volatility through frameworks like design thinking. The rise of generative AI quickly expanded that mission, revealing just how profoundly technology is reshaping the profession.
“I took the chance to dive deep into understanding the technology, the business implications, ethical considerations, and strategic opportunities for legal organizations,” she says. “I’m excited that an unexpected disruptive force is creating incentives that simply didn't exist before to improve legal education, client services, and access to justice.”
At MAICON 2025, Jen will share how legal frameworks are evolving and what companies can do to stay ahead of these changes.
Jen will join Bridget McCormack, President & CEO of the American Arbitration Association–International Centre for Dispute Resolution® (AAA-ICDR®), for a dynamic fireside chat on the fast-changing legal landscape with AI.
Together, these legal leaders will explore both the challenges and opportunities that AI presents for brands that rely on content and intellectual property. Expect candid insights into pressing questions like: Who owns AI-generated content?
“Something as fast-moving as AI creates tremendous opportunities for creators,” Jen says. “It also raises lots of legal murkiness because laws simply don’t move quickly enough to keep up.”
During their session, Jen and Bridget will provide:
For many lawyers, AI’s initial appeal is improving efficiency, using it to draft a contract clause or a section of a brief. But as Jen points out, that utility comes with risks, like the hallucination of case citations – every lawyer’s nightmare.
“But what they don’t fully understand yet is how magical it can be when they use it as a creative thought partner and strategist,” she explains.
After all, clients aren’t seeking a brilliant contract clause or brief; they’re paying for outcomes that advance their business goals.
“So, by zooming out and leveraging AI to think about those more strategic aims, their clients can actually unlock more opportunity than by trying to do the things they’re already using their discrete skills-based training to do,” Jen said.
Jen predicts that the skepticism surrounding AI will begin to fade, freeing up time and energy to focus on “previously unimaginable outcomes using AI.”
That said, she noted that many are at the starting line of their AI journey.
“I think AI literacy will still be paramount in the short term,” she says. “In the small business arena, you’ll start to see a real separation between the companies that are really maximizing what they can do with this technology, whether they are AI-native or AI-emergent.
"Those who have just not kept pace and will very much start to fall behind.”
AI and the Future of Law Podcast
AI and the Future of Law is your essential podcast for understanding how artificial intelligence is revolutionizing the legal industry. Hosted by both Jen Leonard and Bridget McCormack, each episode delves into cutting-edge technologies, trends, and strategies, providing invaluable insights for legal professionals, tech enthusiasts, and anyone curious about the future of law.
Bonus: Jen and Bridget will be dropping episodes throughout the fall season that directly relate to their discussion at MAICON. Tune in to get a preview of their thinking and come to their session prepared with questions!
Building a Law Firm AI Strategy
Developed in collaboration with Jen’s company, Creative Lawyers, this program leverages the American Arbitration Association’s (AAA®) AI transformation journey as a real-world case study, offering participants the tools and insights needed to drive innovation, enhance efficiency, better serve clients, and stay competitive in a rapidly evolving industry.
Fast-Tracked: Emergent Issues in the Legal Profession (Practising Law Institute)
With Jen as your host, this podcast features leading thinkers from the judiciary, legal academia, law firms, corporate legal, alternative dispute resolution, legal operations, and more. Because the landscape is changing so quickly, Jen’s ability to reach legal professionals through the Practising Law Institute’s vast network is especially powerful.
Jen’s Session at MAICON
As generative AI rapidly transforms industries, the legal frameworks surrounding intellectual property are evolving just as quickly—introducing both new challenges and significant opportunities for organizations that rely on content, branding, and creative assets. In this dynamic fireside chat, Bridget McCormack, President & CEO of the American Arbitration Association, joins legal innovation strategist Jen Leonard to explore how businesses can navigate the shifting intellectual property landscape while leveraging AI’s potential for innovation.
Leonard and McCormack will unpack the latest legal and regulatory developments tied to generative AI and IP, including landmark court cases, legislative movements, and emerging best practices. Drawing on Bridget’s leadership at the AAA, they’ll examine how organizations can respond to these changes—not just to remain compliant, but to rethink operations and emerge stronger in an AI-driven world.
Marketing professionals, like their legal and business counterparts, must now grapple with complex questions:
Who owns content generated by AI?
How can companies protect brand identity when AI models can mimic established styles and voices?
And what proactive strategies can mitigate risk while unlocking creative potential?
This session offers actionable insights for turning legal ambiguity into strategic advantage—whether you're leading a brand, developing marketing campaigns, or building AI-powered solutions.
The conversation doesn’t end at MAICON. Keep up with Jen as she continues exploring how law, innovation, and AI intersect:
Follow Jen on LinkedIn.
Learn more about her firm, Creative Lawyers.
Marketing Artificial Intelligence Conference (MAICON) was created for marketing leaders and practitioners seeking to drive the next frontier of digital marketing transformation within their organizations.
We’re excited to host our 5th annual MAICON—Marketing AI Conference—at this pivotal point for our industry. Join us from October 14 to 16, 2025, in Cleveland, Ohio, and use the special code SPEAKERSERIES100 at checkout to receive $100 off your registration!