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In this keynote, Zack Kass explores how AI is reshaping strategy, risk, and decision-making across industries. Plus a fireside conversation.
Second City Works delivers an interactive keynote using improv to strengthen listening, adaptability, and collaboration for navigating change in legal operations.
Judd Kessler reveals how hidden markets shape resource allocation and why design can unlock efficiency, equity, and ease. With examples.
TUESDAY, MAY 12
A former OpenAI executive, Zack Kass explores AI as the most transformative force of our time, ushering in a new era more profound than the Renaissance or Industrial Revolution. He traces its rapid acceleration and addresses critical risks including job disruption, identity challenges, deepfakes, and cognitive decline. Moving beyond concern, Zack reveals AI’s potential to remove low-value work and elevate uniquely human strengths like empathy, judgment, and creativity. He offers a practical framework for approaching this shift with clarity and intention. The session concludes with a fireside chat featuring DocuSign Chief Legal Officer Jim Shaughnessy, expanding on key insights and real-world implications.
Zack Kass is an advisor, researcher, keynote speaker, and the former Head of Go-To-Market at OpenAI.
At OpenAI, Zack led the teams responsible for sales, partnerships, and customer success, turning the company’s cutting-edge research into real-world business solutions. He has personally advised executives across dozens of industries on deploying AI at scale.
As an executive business advisor, Zack now works with Fortune 1,000 boardrooms and leadership teams—including Coca-Cola, Morgan Stanley, and Amgen—to help leaders navigate the rapidly evolving AI landscape.
Zack’s mission is to ensure individuals, businesses, and governments are active participants in the AI-powered future by making the technology both understandable and actionable. He is recognized as one of the foremost thinkers in applied AI, with his insights featured in Fortune, Newsweek, Entrepreneur, AdAge, and Business Insider.
Wednesday, May 13
This keynote from Second City Works, brought to you in partnership with Epiq, blends improv, storytelling, and interactive exercises to show how strong listening drives effective legal operations. It connects empathy, adaptability, and influence to the day-to-day challenges of managing change in complex legal environments. Through guided exercises, participants will experience how listening to understand, not just respond, improves collaboration and decision-making while building flexibility in uncertain situations. A “yes, and” mindset reinforces how to build trust, align stakeholders, and navigate change with confidence. Attendees will leave with practical takeaways to strengthen communication, elevate service delivery, and lead through change.
Bio coming soon
Carisa Barreca has been working professionally with The Second City since 2009. She began her career as a performer on the Resident Stages of this world-renowned comedy theater but has been honored to work with Second City Works in many different capacities over the years. Carisa has performed in live customized and improvised shows, corporate videos, and virtual shows and hosted large-scale events.
In addition to performing and creating with SCW, Carisa is an accomplished director and most recently directed Second City’s critically acclaimed mainstage revue. Carisa’s background, which spans every aspect of Second City, makes her uniquely equipped for facilitation. She knows the importance of infusing humor into her messaging and knows how to team build and create a collaborative environment where people are not only put at ease but excited to learn!
Katie began performing in Washington DC, with iMusical at the Washington Improv Theater and with friends at the DC Improv. Wanting more of this creative art form, she moved to Chicago! She trained at iO and The Second City and now finds herself lucky enough to make a career out of it.
She is an alumni of the Second City e.t.c stage, writing and performing in two reviews: Fantastic Super Great Nation Numero Uno, and previously A Red Line Runs Through It. She currently performs every Sunday with The Late 90’s at Logan Square Improv and at the Annoyance Theater every Thursday night with Super Human. You can catch her in TV shows like Shrink, Chicago Justice, Work in Progress, and commercials.
She has worked for over twelve years with The Second City as a writer, facilitator, and designer of corporate communication training and loves it!
Second City Works is the B2B arm of the world-famous sketch comedy and improv institution. Using the same skills their performers use onstage, SCW helps leading businesses to create a fun, interactive, and unconventional approach to learning and entertainment.
Thursday, May 14
“Hidden markets” allocate some of our most valuable resources, and when they are poorly designed they can have major consequences for our customers and workers. Seeing the hidden markets all around you and understanding how they work can help you unlock new potential. A pioneering researcher in this burgeoning field, Judd Kessler explains how these hidden markets operate and how you can best design them. A highly engaging speaker, Judd interweaves personal stories with deep economic insight. (A story about allocating a single dessert to one of his three kids, for example, illustrates key points about what hidden markets aim to achieve and their limitations.) By the end of Judd’s talk, you will know why hidden markets arise and how can you improve the ones you control to achieve the “three Es” of efficiency, equity, and ease.
Judd is the inaugural Howard Marks Endowed Professor of Business Economics and Public Policy at the University of Pennsylvania’s Wharton School.
In 2021, Judd was awarded the prestigious Vernon L. Smith Ascending Scholar Prize for his path breaking scholarship. For his work on organ allocation, he was named one of Forbes’s “30 under 30” in Law and Policy. He is an award-winning teacher whose courses are popular among undergraduates, MBAs, PhD students, and executives, as well as a sought-after speaker.
His research and writing have been featured in leading media, such as The New York Times, The Wall Street Journal, The Washington Post, Los Angeles Times, Scientific American, Harvard Business Review, Politico, NPR, Hidden Brain, and Freakonomics, among others.
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