[Blog] Generosity at Scale: What MAICON 2025 Taught Me About the Future of Leadership

By Nicole DeMeo, Co-Founder, Outfront Solutions

When I arrived in Cleveland for MAICON 2025, I expected to hear about models, metrics, and marketing breakthroughs. What I didn’t expect was to leave with something far more profound - a renewed faith in humanity.

The real revelation wasn’t the technology.

It was the people.

Across three days, I watched leaders, founders, and practitioners share ideas, frameworks - even failures - with striking vulnerability and generosity. No posturing. No gatekeeping. Just a collective desire to learn, build, and lead better.

In an era when technology often feels cold or transactional, MAICON reminded me that the future of AI isn’t about replacing people - it’s about revealing the best in us.

AI Is No Longer a Project - It’s the Operating System for Modern Business

More than 1,500 business, marketing, and technology leaders gathered to explore one truth: AI is not a pilot program anymore. It’s the foundation of how organizations operate.

The companies accelerating aren’t just “AI-Forward.” They’re AI-First, integrating learning, experimentation, and adaptability into the core of how they work. They aren’t waiting for transformation to happen; they’re designing it.

The Leadership Revolution

Across panels and conversations, a new leadership model emerged - one that redefines ownership, roles, and success itself.

Ownership at the top

AI cannot live in a silo. The CEO sets the intention, pace, and values for transformation. AI is not an IT project - it’s a business strategy.

New roles, new muscles

We’re seeing new titles like AI Product Manager, Knowledge Architect, Governance Lead, and Enablement Leader - roles that bridge vision and execution while building trust and literacy across teams. We’re also designing the roles and organizations of the future and guess who/what has a role on org charts - agents.

Metrics that matter

The leaders I met aren’t measuring only cost savings. They’re tracking adaptability, learning velocity, and time-to-first-value - because speed and creativity are the new KPIs. Expansion with AI for capacity/growth is key.

MAICON Voices That Framed the Future

The stage at MAICON was filled with thinkers who aren’t just predicting the future - they’re building it.

Paul Roetzer (CEO Marketing AI Institute & SmarterX - pictured here) reminded us that every business faces a choice: become AI Native, evolve as AI Emergent, or risk becoming Obsolete. “Every business has the opportunity to disrupt - and faces the risk of being disrupted.”

Jeremiah Owyang (Silicon Valley colleague, venture capitalist at Blitzscaling Ventures) flipped the script on business and marketing: “Your next customer might never visit your website. Their AI will.” He shared a vision of an A2A (agent to agent - no longer B2C/B2B) future. A powerful reminder that trust and transparency will define brand advantage.

Cath Anderson (CCO Akido Labs) brought the conversation back to empathy: “AI should be seen as augmented intelligence, not artificial.” The stories we tell about AI shape how our teams embrace it.

Geoff Woods (author, The AI-Driven Leader) underscored curiosity as the most valuable leadership skill, using his CRIT model - Context, Role, Interview, Task - as a practical guide for communicating with both humans and machines.

Eva Dong (AI Value Lead, Google) grounded it all: “AI for AI’s sake is a dead end. Start with the outcome.”

And Mike Kaput (co-host Artificial Intelligence show & SmarterX) closed with a rallying cry: “AI is a productivity tool. The only way to learn is to use it.”

Together, these voices painted a future shaped not just by algorithms, but by authentic, accountable, and action-oriented leadership.

Generosity as a Competitive Advantage

My biggest takeaway from MAICON wasn’t technical. It was cultural.

The most advanced organizations I saw were also the most open. They share what they’re learning. They teach others. They celebrate progress - not perfection.That’s wonderfully aligned with our values at Outfront Solutions.

In a landscape defined by acceleration, generosity has become the ultimate differentiator. When knowledge flows freely, everyone levels up faster.

This is how innovation truly scales - not through secrecy or competition, but through collaboration and courage. That’s the real “intelligence” behind AI: collective wisdom amplified by empathy.

If generosity is the fuel, leadership is the engine.Together, they define what comes next.

Let’s leap. The net will appear.

Resources:

Organizations, insights and tools, geek out with me:

• The Artificial Intelligence Show (I don’t miss an issue, highest recommendation)

• The Marketing AI Institute (generous with free and paid resources)

  • SmarterX (AI research and education firm)

  • InnovationsGPT (identify and prioritize innovation opportunities for your business)

  • JobsGPT (prepare for the future of work)

• MAICON 2026 (join us next year at the conference)

About Outfront Solutions

Outfront is not a consultancy. It’s a catalyst. We are a strategic acceleration partner for bold leaders and high-growth organizations ready to move with purpose. From brand positioning and go-to-market strategy to AI-powered content systems like Executive BrandOS, we blend insight, storytelling, and smart technology to turn vision into momentum. Whether you're launching something new, navigating change, or building influence, we equip you with clarity, tools and communications that build reputation, relevance, and results that last.