Sidewalk Labs CEO: The 3 Biggest Problems Urban Designers Have To Solve

Daniel Doctoroff shares key lessons from U.S. cities that are grappling with major transportation challenges.

Sidewalk Labs CEO: The 3 Biggest Problems Urban Designers Have To Solve
[Photo: Tony Shi Photography/Getty Images]

As cities across the U.S. face growing congestion, shifting populations, and aging infrastructure, transit problems have become a huge strain on everyday life and a barrier to social mobility, with convenient and affordable access to jobs out of reach for too many hard-working Americans. This combination of limited opportunities, longer trips to work, and terrible traffic congestion makes it harder for working-class families to climb the social ladder.


These troubling trends were one reason the U.S. DOT launched its Smart City Challenge late last year, encouraging cities to use new technology to help close gaps in transportation equity. During our partnership in the challenge, we met with all seven finalist cities to learn more about the problems they face in planning transportation systems, and how we might build tools to help them get people where they want to go faster and more affordably. Those conversations with city officials and urban planners taught us many important lessons.

For starters, cities told us that greater visibility into travel demand, via data, is a critical component to help them plan stronger transit networks. They also made it clear that they’re already developing a more integrated view of transport options across modes, as well as universal farecard technologies to match. And they’re testing new payment methods that can direct transit money to the residents who need it most, regardless of what mode they ultimately choose. Our role during these talks was to learn what the public sector is already trying, and discuss ways to help those trials become successful.

There is no substitute for investing in public transportation, and some cities have taken steps to modernize their mass transit systems. Houston, for instance, recently reimagined its bus system as a high-frequency network aimed at improving access across the city. Digital fare payments and real-time arrival screens have also made life easier for riders. The beauty of effective transit improvements like these is that they offer true mobility freedom, relieving residents from the huge cost burden of owning a car. Strong transit also enhances the density benefits and social interactions that make our cities such wonderful places to live, play, and work.

But one of the most consistent themes we heard was that closing the gaps in public transportation with data requires new transit policy frameworks. When a fixed bus or rail route gets people where they need to go quickly, there’s nothing better for a city. Unfortunately, sometimes that’s just not the reality: a sobering 2011 report from Brookings found that the average commuter could only reach 30% of metro area jobs within a 90-minute transit trip.


That struggle takes its biggest toll on lower-income residents striving for social mobility, whether it’s high-profile stories like the Michigan factory man who walks 20 miles a day to his job, or everyday cases like a bartender trying to get home at 2 a.m. In these situations, where public transit is not only highly unreliable for riders but very costly to operate for taxpayers, cities often connect people with taxis via vouchers, and now they’re looking for new payment technologies to support ride-hail options, too.

Another takeaway from our discussions with cities was their difficulty managing parking. Over-abundant parking can make cities less affordable places to live and creates loads of congestion. If cities can use technology to stitch together existing parking spots into shared or virtual lots, and help drivers navigate to these spots, we can reduce both time spent circling and the total amount of spaces needed. And if they choose to implement dynamic pricing of these parking spots—charging more money at peak times, like successful pilots in San Francisco or Seattle—they can reinvest that revenue right back into the transit system. Cincinnati, for instance, plans to fund the first year of operations for its new streetcar partly with $2.2 million in revenue from new parking fees.

Perhaps the greatest lesson we learned from our partnership in the DOT challenge was just how much cities view data as essential public infrastructure for transportation decision-making. Traditional transit agencies are in a moment of flux. Even as they watch micro-transit services rise all around them, cities don’t have the data to understand and coordinate travel patterns in real time.

To that end, there’s some early evidence that taxis and ride-hail systems can complement transit, rather than compete with it, by encouraging people to rely less on cars or by offering discounted trips to bus or rail stations. These are promising starts, but there are still some big outstanding questions about whether these services will be affordable for lower-income city residents or end up creating more congestion than they relieve. Like so many other partnerships emerging in this space, from SEPTA and Uber to Kansas City and Bridj, we’re still trying to figure out how transit, data, and on-demand vehicles can move forward together effectively and responsibly.

Those are the types of complex mobility questions we’re trying to shed light on as we engage with cities—a collaborative process that’s just beginning and will help inform Flow, the transportation coordination platform that we hope cities can use to tackle these exact problems.


We’re still in the early stages of Flow’s development, and it’s obviously not a cure-all. But we strongly believe that by bringing together new sources of real-time data, Flow can provide a comprehensive picture of where people want to go, and when they want to go there, that’s never been easily available to transportation planners. Our hope is that this streamlining can free up funding for cities to spend wherever they see the greatest impact: that could mean more money for existing services, as well as experiments that close service gaps in places traditional transit can’t easily reach. We want to make sure this transition to a new mobility era serves the public interest and closes opportunity gaps, instead of widening them.

The Smart City Challenge began the conversation about tech-enabled mobility, but we’ve partnered with Transportation for America to broaden it to dozens more cities across the U.S., in the hopes of learning even more. Because at the end of the day, any strong public-private partnership works with cities to understand their unique challenges, and gives them the tools to resolve them on their own. What cities do with these tools—whether it’s run more buses, or expand bike-share networks, or develop connected fare cards, or subsidize shared mobility—is entirely up to them. It can’t succeed any other way.

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About the author

Daniel L. Doctoroff is CEO of Sidewalk Labs and the former deputy mayor of New York City.