Every firm I speak with is at a different stage of the AI journey. Some are full evangelists already building and operating on internal and external tools. Others are AI-curious and experimenting around the edges. And some haven’t touched it at all.
But regardless of where any single firm sits, the reality is clear: AI is rewiring the industry at a faster rate than most imagined. The pace is already out in front of product roadmaps, organizational structures, and legacy processes. Leaders are trying to make sense of what is real, what is noise, and what actions will actually move their firms forward, all while navigating the very real personal side of “what does this mean for me, my family, the future of our profession, and society as whole?”
That dynamic is what led us to build the AI Playground at Future Proof Citywide, March 8-11, 2026 in Miami Beach, FL.
What the AI Playground Is
The AI Playground is a 21,000-square-foot pavilion designed to show what “applied AI” looks like in practice. It’s where attendees can explore real workflows, evaluate tools, and learn directly from operators, advisors, technologists, and founders who are already integrating AI into their businesses.
We built it to make innovation tangible. Rather than more abstract conversations about disruption, you will see how AI is transforming the work financial firms do today, not someday.
Alongside sponsor activations and live demos, the AI Playground is organized into three core areas:
- The Show & Tell Stage
- The AI Sandbox
- The Level Up Area
Each plays a different role in helping our community build a clearer view of where AI is taking the industry.
1. The Show & Tell Stage
This stage brings together executives, advisors, engineers, and product leaders to walk the audience through real work. No slides. No theory. Each session focuses on a specific workflow or use case and shows exactly how it is being improved with AI.
Sessions may include:
- Vibe Coding: Building Custom Tools with AI: How professionals use AI to quickly build their own lightweight tools and workflows without traditional development. These sessions show how advisors and operators are turning complex processes into simple, custom applications by describing the problem and letting AI generate the solution.
- Data Infrastructure for Mid-Size Firms ($1B–$10B): A focused discussion on how to unify data, clean it, and build a functional data lake that actually supports AI, without over-engineering or overspending.
- AI-Powered Financial Coaching: Demonstrations of conversational AI designed to help clients between advisor touchpoints. You’ll see how firms are experimenting with nudges, behavioral cues, and progress tracking that personalize engagement without replacing the human relationship.
The value comes from practitioners talking candidly about what they built, where they started, and the lessons they learned. It is visibility into the decisions happening inside firms right now.
2. The AI Sandbox
The AI Sandbox is an intimate space for pre-scheduled discussions that dive into practical AI topics. This format debuted at the Future Proof Leaders Retreat and received the strongest feedback of any part of the program.
These discussions are not panels. They are peer-to-peer working sessions. Each conversation brings together people with relevant experience or shared challenges.
Sample topics include:
- Building Your AI Committee: How firms structure internal groups to guide responsible AI adoption. These sessions cover governance, explainability, and fairness frameworks, alongside the messaging and rollout strategies that help organizations overcome fear, resistance, and pilot fatigue.
- Rewriting the Org Chart for AI-Native Firms: A working session about reorganizing teams around intelligence loops, not legacy functions. Participants examine how roles evolve as more workflows become automated or agent-supported.
- Designing Incentives for Innovation: A candid discussion about comp plans, experimentation, and how to reward speed, creativity, and measured risk-taking across the firm.
The goal is to accelerate learning by creating a space where leaders can exchange what is actually happening within their organizations, including the hurdles that rarely get discussed publicly.
3. The Level Up Area
The Level Up Area is where attendees sharpen their technical and human skills. Every session is practical and designed to be immediately useful.
Sessions could include:
- AI Literacy for the C-Suite: How executives assess risk, set direction, challenge assumptions, and build the organizational guardrails needed for responsible adoption.
- Upskilling the Workforce: Tools and training to help advisors, planners, and operations teams integrate AI into their daily workflows and support clients who use AI themselves.
- Wellbeing in the Age of Automation: How leaders maintain culture, purpose, and psychological safety as the pace of change accelerates and roles evolve.
Attendees will walk away with frameworks, checklists, and workflows that can be applied as soon as they return to the office.
Why We Built It
As an industry, we are past the stage where simply knowing about AI is enough. Firms now need to understand how to apply it. Many leaders I speak with say they are under pressure to deliver an AI strategy but lack visibility into what is real, practical, and achievable.
The AI Playground closes that gap. It brings together the people who are building, experimenting, and implementing AI inside their firms, and creates a shared environment where the entire ecosystem can learn from each other.
Future Proof Citywide is where AI meets finance. The AI Playground is where that shift becomes real.
Advancing the Future of Finance Through Collective Learning
The only way the industry moves forward is by bringing real work into the open and learning from one another. The failures, the wins, and the hard lessons all matter. When we share them, we build stronger firms, stronger professionals, and a community that is truly AI-ready.
Join us at Future Proof Citywide in Miami Beach March 8-11, 2026.
The next 24 to 36 months will reshape how financial firms operate, how work flows, and how clients are served. Leaders across wealth, fintech, asset management, and banking are moving quickly to understand what comes next.
Register for Future Proof Citywide 2026
Secure your place at the largest AI-native finance event. Join 4,000+ leaders across wealth, fintech, asset management, and banking for three days of applied learning, networking, and 30,000+ pre-scheduled meetings. Register now.
Inquire About Sponsorship Opportunities
If your company is interested in exhibiting inside the AI Playground or participating in Breakthru Meetings, our team can walk you through sponsorship packages, hosted meeting options, onsite activations, and brand integrations designed to help you reach senior decision-makers across the financial ecosystem. Reach out here.
Author
Matt Middleton
Founder & CEO, Future Proof
Matt Middleton is the founder and CEO of Future Proof, the company behind the world’s largest AI-native finance event, Future Proof Citywide. He leads the vision for building community-driven experiences that connect the most forward-thinking investors, advisors, technologists, and creators redefining financial services.
Disclaimer: This article was written by me … with the help of AI (ChatGPT 5.1 to be specific). If we’re building an event about how AI is transforming finance, we’d be hypocrites not to use it ourselves. At Future Proof, we’re testing and deploying AI at every stage of the business: from how we research and write, to how we design, plan, and deliver events. Consider this both an experiment and a preview of what’s to come.
