Diagnose Your AI Gap: A Working Session for HR and Technical Leaders
with Mara Gates
Beyond the Pilot: How to Lead an AI Transformation That Sticks
Hunter Lee Canning, Eryn Peters, Ken Sterling
October 14, 2026 02:00 PM EDT
October 14, 2026 02:00 PM EDT
Virtual
Most AI initiatives don’t fail because of the technology. They fail because companies underestimate how much the right people, in the right roles, with the right implementation support around them, actually matter. In this session, leaders from across industries will share what separates organizations that scale AI successfully from those that don’t, including real examples of transformations that built lasting internal capability and left teams confident enough to own the work themselves.
Topics will include:
- AI initiatives stall on people and process, not technology. The organizations that scale successfully are the ones that invest as much in the right roles and implementation support as they do in the model itself, because that's usually where the gap actually shows up.
- Scaling AI means building internal capability, not just running a pilot. The difference between a one-off proof of concept and a lasting transformation comes down to whether teams develop the skills and ownership to carry the work forward on their own.
- Confidence is the real marker of success. The organizations that get AI transformation right leave their teams feeling equipped and trusted to own the work themselves, rather than dependent on outside support to keep it running.
This event will be eligible for SHRM credits.
Meet The Speakers
Hunter Lee Canning
Founder of Plumwheel & PowerToFly Virtual Event Host
Hunter Lee Canning (he/they) is allergic to corporate jargon and proud of it. With two decades in Hollywood and over 800 virtual events hosted, Hunter delivers no-BS keynotes showing B2B teams how to break free from boring 'professional' presentations. As the queer, neurodiverse founder of Plumwheel, Hunter has perfected this approach by turning conversations into compelling video campaigns that boost engagement 300% for growing companies and enterprises. Sales teams love them, CFOs fund them. Go figure. You can connect with Hunter on LinkedIn.
Eryn Peters
Co-Creator @ AI Maturity Index
Eryn is a future of work evangelist, retired digital nomad, workforce expert, and scale-up builder. She is the founder of Startup Consortium, editor of Weekly Workforce, and Co-Creator of the AI Maturity Index. Before founding Startup Consortium, she built two unicorns in the staffing industry where her work has helped 4.5 million people in over 190 countries access new learning and job opportunities.
Ken Sterling
AI, Tech and Media Attorney, Sterling Media Law and Opus Intelligence Labs
Ken Sterling is not a lawyer who learned technology from the sidelines. He has been coding since 8th grade, worked at Intel, earned Cisco CCNA, Microsoft MCSE, and CompTIA A+ certifications, and built data centers before becoming a lawyer. Today, Ken is a Century City technology, AI, media, and business attorney, VC LP, entrepreneur, USC professor, and board advisor with a rare blend of legal, technology, media, and operating experience. He co-founded an early cloud CRM company that was partially acquired by KPMG, then co-founded a bank, and in his earlier years, co-founded a global manufacturing company. Ken serves as general counsel and strategic advisor to technology and growth companies, advising founders, executives, investors, platforms, and media businesses on law, capital, AI, data, intellectual property, transactions, reputation, platform liability, and business strategy. He teaches at USC Gould School of Law and USC Annenberg, serves as General Counsel to Opus Intelligence Labs, and writes as a columnist for Forbes and Inc. Magazine.
