Leading with Purpose in a Disrupted World

SCOTT SHEPARD

Founder & CEO,

The CitiesFirst Advisors

By 2050, nearly 70% of the world’s population will be living in cities. That’s not just a statistic—it’s a seismic shift that will redefine how we move, work, and live. Today, cities are already struggling with clogged streets, polluted air, and aging infrastructure. And with transportation responsible for nearly a quarter of global carbon emissions, the need for a smarter, greener approach has never been more urgent. But the answer isn’t as simple as adding more electric cars or expanding subway lines. “The future of urban mobility isn’t about more vehicles—it’s about fewer, smarter, and better-connected solutions,” says Scott Shepard, a leading voice in the mobility revolution. With over two decades of experience at the crossroads of AI, urban planning, and transportation, Scott has made it his mission to rethink how cities move. As the Founder & CEO of CitiesFirst Advisors, he collaborates with governments, startups, and corporations to design forward-thinking mobility strategies that prioritize efficiency, accessibility, and sustainability. And he’s not just talking about change—he’s driving it. From shaping commercial strategy at Free2Move to navigating policy and government affairs at Drover

“What works in one city won’t work in another; start small and show how change pays off.”

AI, Scott has been at the forefront of mobility innovation, influencing policies, developing technologies, and leading business growth. Through The CitiesFirst Podcast, he brings together global experts to tackle the big questions about urban transportation, while his work with InterMobility and Green Mobility Magazine keeps him plugged into the latest industry shifts. But where is urban mobility really headed? Can AI and emerging technologies truly redefine how cities move, or are we simply layering new tech onto old problems? To get to the heart of these questions, TradeFlock sat down with Scott Shepard to discuss his journey, his vision for the future, and the innovations set to transform urban mobility as we know it.

What inspired you to start The CitiesFirst Podcast, and how does it reflect your vision for urbanism and mobility?

Cities don’t work in silos—so why were conversations about urbanism, mobility, and decarbonization so disconnected? In 2022, I launched The CitiesFirst Podcast to break that pattern. I wanted a space where industry leaders could speak candidly, making these complex topics more accessible and engaging. “Cities, transportation, and sustainability are deeply connected—our conversations should be too.” That’s the heart of CitiesFirst—a platform that brings these intersections to life, helping listeners see the bigger picture.

What’s the biggest mistake mobility startups make when integrating into city infrastructure?

Mobility startups often underestimate just how slow and complex city partnerships can be. Public procurement isn’t a quick deal—it’s a long game. If a startup only has 12 months of runway but needs to close multiple city contracts to impress investors, they’re already on shaky ground. “Without a clear path to rapid adoption, many mobility startups end up racing to the bottom instead of scaling up.” Understanding the sales cycle and aligning product-market fit with city needs is key to survival.

What are the three biggest hurdles to fully decarbonized urban mobility, and how can they be overcome?

Decarbonizing urban mobility faces three main challenges: politics, culture, and finances. Politically, cities sometimes backtrack on their climate goals, so it’s important to focus on leaders who stay committed. Culturally, solutions need to be tailored—“What works in one city won’t work in another; start small and show how change pays off.” Finally, finances are tough, but cities can help bridge the funding gap through publicprivate partnerships and investment.

How does your experience across government, consulting, and startups give you a unique edge in urban development?

I’ve been on all sides—government, consulting, and startups—so I know how the game is played. Urban development isn’t just about policies or projects; it’s about knowing how to cut through the noise and get things done. I help clients navigate the complexities—partnerships, city outreach, fundraising—while keeping one goal in mind: building better cities that actually work for people.

What leadership lessons have you gained from working across continents and cultures?

Moving to Europe in 2017 and working across continents taught me some key leadership lessons. First, humility— each culture has its own way of doing things, and it’s crucial to respect that. Second, listening—before offering advice, you need to truly understand the problem. “Listening first, speaking second—that’s where the real impact comes from.” And lastly, curiosity: the more you immerse yourself in new places and experiences, the more you learn and grow.

"Cities are reimagining their spaces, and people are finally taking the lead.”

If you were to write another book, what would its title be and what core message would you share?

I’m actually in the middle of writing a new book this year! It’s called “#CitiesFirst: Urbanism & Mobility in the PostCOVID City.” It’ll dive into how the pandemic changed the way cities think about mobility and public spaces, with a special focus on decarbonization. I’ll feature case studies, best practices, and insights from more than 20 past guests of The #CitiesFirst Podcast. “Cities are reimagining their spaces, and people are finally taking the lead.” Stay tuned for pre-launch details!