You Rushed to Hire a Chief AI Officer. But Who is Your Head of Cities?
As companies obsess over digital futures, they risk abandoning the very real places that shape human experience. It’s time to give cities the same strategic attention given to AI.
For the past decade and a bit, companies have busied themselves trying to make themselves digital. A perfectly sensible thing to do in a world of iPhones and high speed internet connections. As a result we’ve seen waves of Heads of Innovation or Digital, Transformation Directors, EVPs of Customer Experience and now Chief AI Officers.
It’s actually amazing how quickly the digital realm has eaten its way through culture, commerce and everyday behaviour as people get the phones out the moment they’re left alone … worse when there’s a couple sat opposite each other starting into screens rather than each other. Some studies suggest the average person checks their phone nearly 100 times a day, but that doesn’t mean their real world stops existing.
This is a problem though. While everyone has been obsessing over digital, and the mountains of data sitting behind it, they’ve somehow forgotten something quite important, and really rather obvious … customers still live somewhere.
Like cities.
For while they might do lots of things digitally, we are thankfully not living in a world where everything takes place through a screen. We like to think of iOS, Android or Desktop being a platform, but the physical realm is too. More than 55% of the world’s population already lives in cities, and that will rise to 70% by 2050. So why are we ignoring this shared operating system?
Cities are not simply markets or addresses, but the software and the hardware of daily life. They are the places where we gather, move, dream, worry, celebrate or even complain. Cities shape how people live, who they meet, what they value and how they navigate the world. They decide whether a service is even reachable, whether a store feels welcoming, whether a brand has a chance to lodge in someone’s head on a walk home from work. Cities are the big unknown that we typically can’t gather any significant numerical data on that is impacting behaviour of the people that work for us, shop with us, bank with us etc.
“We know more about the habitat of mountain gorillas than we do about a good urban habitat for homo sapiens.” - Jan Gehl
So if companies are truly serious about customer centricity, innovation, growth etc. they need to stop treating the city as a neutral backdrop. Instead, they should treating it as the primary operating system of human experience, and that means creating roles with the mandate, resources and the authority to ask “how do we belong here?”
So my argument is that any meaningfully sized company needs a new role. They need a Head of Cities.
Cities Are the Original Interface
Every journey begins somewhere physical. No matter how frictionless the app or the website or the digital advertising is, the customer’s day is already shaped by the physical realm far more than it is by the phone. They rush for the bus, sit in traffic, navigate construction on the sidewalk, see the world from a public bench, maybe even speak to a stranger, navigate a busy high street, stand in line for coffee, glance at a new building going up, or notice an old one being torn down. Their emotional and cognitive load is profoundly influenced by place, all influencing their mood when the digital presence comes into play.
“Cities are platforms for collective improvisation.” - Dan Hill
Think of the city as the ultimate user interface; chaotic, participatory, constantly being stress tested by millions. It decides what gets noticed, what gets ignored, how people move and whether they even have the energy or optimism to consider what someone is offering. While this is almost impossible to statistically and objectively measure, if we’re then ignoring that interface, it’s basically ignoring the most powerful funnel a company has.
If you can obsess over TikTok engagement, why can’t you obsess over how people feel walking to your store?
Too many companies see the city or even the physical realm as a problem for their corporate real estate teams to manage in the form of store or office leases. It’s a massive missed opportunity, for the city is not just a container to be dealt with, it’s an enabler, collaborator, cultural engine and context shaper. If you don’t design with it, you’re designing against it.
What Would a Head of Cities Actually Do?
This role shouldn’t be confused with a Head of Facilities type who basically ensures their offices are all above board and compliant, with the right number of desks and coffee machines, or someone figuring out if the lease they’ve been offered is good value. A Head of Cities is really more of a strategist with a sense of imagination, endless curiosity of people, a feel for place, the mind of a marketer and a commitment to communities.
“The most creative ideas emerge from dense, diverse, urban environments.” - Richard Florida
They would spend far more time out and about, rarely spending two days in the same place, certainly not buried in a laptop screen, or back to back video calls, so they can understand the patterns and rhythms that define the pulse of where their organisation operates. They’d pay attention to where people linger, where they rush, what bottlenecks they curse, what shortcuts they invent, what gaps they fill on their own because no one else bothered to. It might be rethinking the appeal of coming to, and spending time in the office, for employees. Perhaps the experience of a day downtown, and the impact on retail and hospitality. It might be how the city influences communication and community for a telecoms business.
They’d treat friction points as opportunities, so faced with a broken bit of public realm, maybe their company can help fix it. Not as a cheap branding stunt, but as a meaningful intervention. A neglected stretch of footpath between two stations perhaps has the potential to be a pop-up activation, a rest stop or a creative experience that could transform it into something people will remember, rather than complain about.
A Head of Cities would also champion contextual relevance, so it’s not the same global playbook expected to copy and paste from Toronto to London, or Shanghai to Copenhagen. They’d advocate for sharing learning from place to place, considering what might be insightful, what the implications would be, and thoughtfully applying the right bits. Maybe that’s a store format, a delivery system, a way of working, a piece of corporate philanthropy or a shared challenge. Ultimately, the outcome should be brands that feel of the city, not just in it.
And perhaps most importantly, they’d see the city not just as a place to do business, but as a platform for experimentation, innovation and opportunism. Cities are living laboratories, constantly prototyping better (or worse) ways to live, play and work together. Charles Landry calls them “permanent workshops” where culture, behaviour and meaning get tested in real time.
All companies can learn from that, and need to regain that spirit, confidence and enthusiasm for testing in public, learning from real people and seeing how interventions ripple outward in ways that can’t be determined in advance.
Who’s Already Acting Like They Have One?
Some organisations already behave as if they had a Head of Cities, even if they never called it that, and nor that they should either.
Apple is perhaps the obvious example, with their flagship stores designed with a bit more care, akin to civic architecture. They are for shopping, but also service, which perhaps justifies a bit why they try to make them act like landmarks woven into the urban landscape. Glassy, open, generous, they invite people to linger, without buying. While they could do a bit more as a piece of privately owned public space, they go beyond the efficient minded way of selling most other electrical products.
Starbucks used to be a leader in this realm, as the company built itself around the idea of a third place, that is neither home nor work, but part of a person’s daily social fabric.It’s a profoundly urban idea, meeting people where their lives actually happen. However, the company has somewhat lost its way over recent years, so the locations can feel tired, overcrowded, shabby, unwelcoming to sit in even. It’s a tricky task in a world of digital nomadism as the coffee shop can easily become a haven for the laptop at the expense of something more welcoming and community driven. But the fact Starbucks used to be so good at this, should be a sign of a territory to reclaim.
REI is another great example. Every year, they close their stores on Black Friday, encouraging people to go outside instead. That’s more than a PR move, for it’s a signal that they understand their brand is strongest not on a shelf, but in the forests, trails and parks where their customers actually use their products. Sometimes, we need a mindset to do the opposite of the established benchmarks in order to a) stand out and b) work out what really matters.
Shinola, meanwhile, didn’t just make watches in Detroit, it made Detroit part of its brand. The city’s grit, story, resilience and aesthetic were embedded in every product. The city effectively became the brand, but to get there, one had to understand and care for the city itself.
These brands all, in their own ways, have shown what a Head of Cities might do in helping their companies build credibility, trust and belonging through a thoughtful relationship with place.
Why Now?
Cities are in a precarious place with a whole range of pressures. Many are politically fragile, and financial hamstrung. Somewhat stuck between the local, national and international power centres. Look at the financials of most municipalities and you will discover cracks, as well as some gaping holes in the books.
The pandemic cracked open how we think about work, home, commuting, shopping etc. Most downtowns have still not really recovered. (Over 70% of downtown office leases in major North American cities are still below pre-pandemic occupancy.)
Climate change is forcing radical rethinks of transport, energy and building codes. Housing has turned from a polite middle class dinner party topic into a fierce battleground for justice and fairness. The prevalence of digital and social media have influenced our grasp of current events, eroded many local communities as well as enabled others.
In other words, the city is in flux. Lots is uncertain, the strains are being felt, in some cases the pressure is too much to handle. I am also consciously aware that the profession of urban planning, has itself many of the same challenges of risk aversion, regulation adherence and sterilisation of the soul that companies have, typically stemming from the likes of compliance, HR and finance teams. It could also be, that a creative, innovative, curious instigator sitting in the realm of the corporation, can be a strong counterbalance to the conservative culture that has taken hold in both public and private sector organisations.
In this kind of moment, companies have a choice to make. They can sit on the sidelines, treating cities as a bit of an afterthought, and ultimately the responsibility of someone else to shape for them. Or they can engage, with humility, creativity and respect, to help build places that work better for everyone.
Companies willing to show up in cities, listen to them, invest in them and experiment with them will earn a level of cultural permission that no ad campaign could ever buy, or any office of the future could possibly offer in terms of workplace culture.
The Return to the Real
The shift perhaps hiding in plain sight just now, even as companies scramble to automate and optimise, and the internet floods with endless AI-generated everything … product copy, images, social posts, news articles, reels of ‘human’ faces … people are reaching a saturation point.
When every scroll feels the same, every recommendation eerily predictable and every brand voice basically an interchangeable algorithm, the hunger for what’s real grows stronger.
Cities, in all their messy, unpolished, unpredictable glory, are the perfect antidote to digital sameness. They offer friction, surprise, accidents, creativity and texture. No chatbot can replicate the vibe of a buzzing plaza on a warm night, or magic of a new restaurant where there’s a chance to taste something new or even the time that you might look at a mural someone actually took the time to paint themselves.
As AI makes the online experience more homogenous, cities can become a place for companies to develop a competitive advantage, as a living, breathing counterweight to content sludge. But only if they choose to invest in them, to show up and do so respectfully, rather than cynically.
The companies that will win in the AI-saturated decade ahead won’t just have the best digital assets, they’ll have the most authentic, rooted, physical and human awareness, as well as presence.
Making It About Participation, Not Gentrification.
There is a crucial difference between parachuting into a city to sell things, and participating in its life. A Head of Cities should not be an emissary of gentrification, smoothing over communities with pastel branding while prices soar and locals get pushed out. That story is all too familiar, and toxic.
Instead, a Head of Cities should stand for something more earnest, i.e. showing up, getting involved, being willing to listen, to adapt, to collaborate. That means respecting what a place already is, and what it aspires to become, but also having an opinion on what it could be too. It means co-creating value with people who live there, not extracting value from them.
It’s a bit like what those early Heads of Innovation were good at, in that they started by observing, meeting, mapping and then acting. So they built relationships with the likes of startups, accelerators, investors, industry organisations, even competitors. What they created was often more interesting, creative and unexpected compared to those that let their immediate agenda lead them.
If a brand believes it is part of the community, then it has to accept being held accountable to the community, because cities have memories and they remember who invested, who left, who cared, as well as who didn’t. They remember the investment that brought life to a forgotten laneway, the company that supported a local artist, the brand that showed up after a flood. And they remember who treated them as a market rather than a place.
So while every company is eagerly trying to figure out how AI will be a critical part of their future strategy, we also need to remember that the next decade will also be won by companies that understand how to matter in place, not just online through devices. The future is far more stubbornly, beautifully, complicatedly local as it is digitally global.
So if you want your brand to be relevant and resilient into the future, then you need to claim a role in the civic stories. And to do that, we will need people who can see cities as living organisms, with their own rules, dreams, uncertainties and contradictions.
That’s why we’ll need these Head of Cities type roles and mindsets, someone is there to ask the messy and complex questions, that the dashboards and reporting doesn’t really capture. How do we belong here? What context are we operating within? Where are the barriers to us delivering on our promise? How do we make life better here? How might we have a positive impact on our people and surroundings?
This shouldn’t be a someday conversation, the moment is really now. Some cities are actively rebuilding, reimagining and reaching for something new; while others need all the help they can get. Companies that care about this will vastly outperform those that behave more like ‘placetakers’, than ‘placemakers’ too.
If there was ever a moment to step up, this is it.