By Michael Fitzgerald

It was an early-spring morning, and Chris Osgood '99,“urban mechanic,” was deep inside Boston City Hall's parking garage.

Outside the sun was glorious, brightening even City Hall's stark Brutalist architecture. But Osgood was in the artificial light inside a truck, looking at an oversized blue vending machine filled with things like duct tape, work gloves, and safety vests. Next to him, another blue vending machine with windowed lockers held power tools.

He stood there, wearing a collared shirt and tie, sleeves rolled up, gazing through steel-rim glasses as he listened intently to a spiel on how the vending machines would help the city cut 50 percent from its costs for supplies in just the first year of use.

Vetting industrial vending machines does not appear in Osgood's job description. But as co-director of Boston's pioneering Mayor's Office of New Urban Mechanics, he's a kind of minister without portfolio whose work encompasses a wide array of duties. In this case, officials from several city departments, including the Public Works commissioner, have heard similar spiels on this machine, and they wanted Osgood to look at it. That means there's a problem that they want solved, and they're asking one of their vaunted new urban mechanics to get under the hood and make some recommendations.

As he listens, Osgood asks questions about how the machines work, and especially how officials can see reports on what's being used and spent. As he hears the answers, he sees real potential to solve a problem and make the city run just that much better.

“It's great to be in this truck!” he tells them. And he means it.

As an urban mechanic, Osgood tinkers with the city as a whole, working across city departments to help them adopt new technologies and methods so they can engage more closely with citizens and provide better service. Launched more than four years ago, the Office of New Urban Mechanics has done so well that when Boston changed mayors, the new mayor, Marty Walsh, not only kept the office, he expanded it. The groundbreaking work done in Boston has led to similar efforts in other cities, including Philadelphia, whose Office of New Urban Mechanics opened two years ago.

Osgood has been interested in cities since he was a kid. He spent his first nine years in Boston's Beacon Hill neighborhood, before his family moved to nearby Brookline. His father, a banker, was active in the city's arts and preservation communities, and would take Osgood and his older brother for walks and tell them the back stories of public art. Osgood's father also had a collection of old prints of the city and old books about Boston. Meanwhile, Osgood's mother, a teacher, took them to the city's excellent museums and aquarium.

In high school at Milton Academy, Osgood took a class on American poverty that included spending time volunteering at Boston-area shelters and exposing him to a different part of the city. He deferred college for a year to work with AmeriCorps' City Year program, landing

a placement as a teaching assistant in a kindergarten class in a Boston elementary school with a large Cape Verdean population. (Osgood says he can still sing the Barney theme song in Cape Verdean Creole, a variant of Portuguese.)

In college, he found his way to Bryn Mawr's Growth and Structure of Cities program, and he says he knew from his first paper in an“Urban Culture and Society” course that he had chosen the right major. He wrote about an open space in Philadelphia, the Clemente Park and Playground, and how its design shaped the activity and social life of a neighborhood.“I loved it and was off from there,” he says.“I probably over-majored.”

Osgood says he was fortunate to be in the Growth and Structure of Cities program when its founder, Barbara Miller Lane, was still teaching. (She retired in 1999.)“She's a remarkable person,” he says, noting that the interdisciplinary mix of courses he experienced in the program continues to shape his work.“I talk to people all the time who feel like they're not using their undergraduate program in their day-to-day life. I feel like I use mine all the time.” It was an especially apt program for someone who wants to change cities across departments.

But, nearing his Haverford graduation in 1999, Osgood wasn't thinking about working for a city at all. His work experience had been at City Year, MASSPIRG (Massachusetts Public Interest Research Group), and the Pennsylvania Environmental Council, all nonprofits. But a recruiter from the New York City Department of Parks & Recreation came to campus, and Osgood signed up for an interview. The department offered him a spot.

New York's Parks & Rec is steeped in city shaping; it was the domain for 26 years of Robert Moses,“the power broker,” one of the most influential urban planners ever. Moses' old office is now the department's conference room. Another legend of urban planning, Frederick Law Olmsted, also maintains a palpable presence in the department, which is headquartered in Olmsted's crown jewel, Central Park.

In New York, Osgood started out as the advance person/staff assistant for a Parks & Rec commissioner, traveling around the five boroughs meeting constituents. He eventually became that commissioner's chief of staff, and later was chief of staff and then senior advisor to another commissioner. When Michael Bloomberg became New York's mayor in 2002, replacing Rudy Giuliani, Osgood found himself fascinated by Bloomberg's approach to running the city.“He looked at leading a city as a major strategic and managerial challenge,” says Osgood.

Bloomberg's style crystallized for Osgood that he didn't want to write public policy.“I was most interested in how cities create value for their constituents,” he says. That realization led Osgood to Harvard Business School. Having worked in nonprofits and government, he thought he might go into private industry and learn its role in shaping cities. But at a panel on careers, he heard a speaker who was working in the Boston's Mayor's Office as a Harvard Business School Leadership Fellow. Osgood decided then and there he wanted to do the same thing, and after graduating in 2006, he went off for his one-year fellowship, which has turned into 7½ years of working on (and for) the City of Boston.

Osgood and his co-director of the Office of New Urban Mechanics, Nigel Jacob, are sitting one day in May in a small fifth-floor conference room in Boston's City Hall, behind a door just off the capacious reception area for the Mayor's Office. Osgood and Jacob started as Leadership Fellows on the same day. They've worked together closely since then, in a kind of ongoing dialogue about how to make their city better.

Asked why governments aren't considered innovative, Osgood says,“The services aren't seen by people as services. There was a study by two professors at Harvard Business School—”

“It's always ‘HBS,' ” interrupts Jacob.

“I know, I know,” Osgood says, smiling.“The study asked, ‘Do you take advantage of any government services?' And people said no. But if you ask, ‘Do you use the mortgage deduction' or ‘drive on streets' or ‘have kids that go to the public schools,' well, of course they do.”

The pair has developed an effective partnership, playing to each other's strengths, Jacob's Mr. Outside to Osgood's Mr. Inside.“I've always been the wonk and Nigel's always been the explorer,” Osgood says. What they share is a passion for Boston, and for using technology to make the city more engaged with its citizens.

Neither was hired to be an urban mechanic, a term originally flung as an insult at Thomas M. Menino (Boston's mayor from 1993 to 2013), meant to make him look like he had no vision for the city. Menino took the slur and turned it into a badge of honor. But there was no formal office around it. Menino says that got started, in a sense, because of Osgood.

“Chris came to me and said, ‘We should be using technology in urban areas,' ” says Menino, now co-director of Boston University's Initiative on Cities.“I said, ‘What's your mind on? Why should we do this?' ” Menino is famously technology averse, loath even to install voicemail at City Hall during much of his time as mayor. Osgood and Jacob believed that the rise of the iPhone and other smart handhelds meant that cities had a new way to engage with citizens, and Boston needed to take advantage of it.

“He showed we could do it,” Menino says.

One of the early efforts was a customer-relationship management program, called LAGAN, that helped transform the city's service departments, making them quicker to respond to requests from a citizen hotline. Potholes are now, on average, filled in around two business days after being reported. Sidewalk repairs have also been speeded up, and burned-out streetlights are replaced more quickly.

Another early project, developed before Menino formalized the roles of Osgood and Jacob by creating the Office of New Urban Mechanics, was the app Citizens Connect, which lets citizens report potholes from their phones, using their GPS to set locations. Citizens Connect, launched in 2009, has been downloaded by tens of thousands of people. Through it, the city was able to turn residents into virtual eyes and ears, and to respond to what they reported. The app has been copied by scores of cities.

Osgood may be Mr. Inside, but that doesn't mean he only haunts City Hall. He and Jacob worked with local entrepreneurs and the Public Works Department to create Street Bump, an app that uses a smartphone's accelerometers and GPS to measure where roads are bumpy and automatically send information to a city database. The goal was to know where street repair crews were most needed. But the challenge was how to test the app. Actual potholes needed to be hit to gather data and see if the phone revealed a difference between regular roads and bumps. Osgood doesn't own a car (he usually bicycles to work). He had in the past borrowed his sister-in-law's car, but“I could no longer borrow her car for my experiments,” he says. Jacob wasn't willing to give up his axles to the cause. The two eventually found a willing accomplice in a press officer, who proceeded to drive them around Boston Common 20 to 30 times in the city's press car, hitting every pothole they could find.“It was not, like, reckless,” Osgood says of their driving.“The press office needed zero encouragement to be part of this.”

They found that the accelerometers did show bumps in the road. Street Bump was developed further and released as an app on the iPhone. Now they are working on a way to automatically dispatch road crews, instead of having to send an inspector first to look at the bumps.

Most of Osgood's days don't involve pothole drive-bys. In a typical week, he and Jacob spend about a third of their time meeting with officials from various city departments to talk about needs and possible new technologies, about a third working on developing ideas, and about a third meeting with people from outside the city who have ideas to pitch, like the local tech entrepreneur who wanted to pay his parking tickets from his phone. (That resulted in TicketZen, launched last year.) Another pitch from a woman who had an idea for a tablet app that could help teach autistic youth resulted in Technology for Autism Now, which the urban mechanics helped build and test.

They also give time to other cities. Story K. Bellows, co-director of Philadelphia's Office of New Urban Mechanics, says Osgood and Jacob have been instrumental in helping her office get started, sharing advice and expertise. When it launched, the two came down on the train from Boston along with the city's then chief information officer. Bellows says they patiently answered Mayor Michael Nutter's questions even after it was time for them to catch the last train out. Nutter wound up giving them a police escort so they could make their train. Even now,“we're on the phone at least once a week,” she says. Philadelphia has adapted some of the Boston projects for its own use, and Boston has also adapted at least one Philadelphia program, a project called FastFWD, which encourages civic entrepreneurs to develop new approaches to social problems. (Philadelphia is focused on urban safety, Boston on education.) The two offices jointly applied for funding from the Knight Foundation for a program called Community PlanIt, which encourages citizens to play a civic engagement game and get involved in community planning. They also have a joint web site, newurbanmechanics.org.

Bellows says Osgood“is incredibly visionary,” and lauds him for his patience and his ability to create things that provide benefits across city departments and for residents. She says he and Jacob are“baking this into the DNA of how government works in Boston. That's a real testament to their success. It's a whole lot bigger than just them.”

Osgood's ideas also matter for cities that don't formally have urban mechanics.“Most mayors in America aren't big-city mayors, and most don't have the ability to innovate or the budget to innovate,” says Adam Wood '00, Osgood's Haverford roommate and the chief of staff for the mayor of Bridgeport, Conn. What Osgood has done is give mayors like Bridgeport's an innovation incubator, spitting out ideas that other cities can then copy. Bridgeport modeled several programs after Boston's, like Be Connected, which lets residents take photos of things in the city that need fixing and upload them to a city database.“It's a fantastic model,” Wood says, noting that Bridgeport officials have gone to meet with Osgood and Jacob.

Wood says Osgood was already driven by the same passion for making cities better when he was in college.“He was all the time volunteering and doing things. He's always been deeply concerned about urban issues, whether poverty or lack of access to quality education.”

Osgood isn't just an urban mechanic. At 37, he's learning to play the banjo. He's also learning to bowl, by visiting all of Boston's candlepin lanes. He ran this year's Boston Marathon, raising money for Alzheimer's, in honor of his father, who died last year. Osgood also loves the outdoors. He and his girlfriend have hiked 2,000 miles of the Appalachian Trail and climbed all the 4,000-foot-plus peaks in New England. But work—the work of making cities great preoccupies him most of the time.

“You have to understand his DNA,” says Menino.“He's all about service. He'd volunteer to work the phone lines to be of service. We have young people who don't want to work in government. Chris appreciates government.”

Michael Fitzgerald is a freelance journalist in Cambridge, Mass. His work has appeared in The BostonGlobe, The Economist, Fast Company, The New York Times, The Wall Street Journal, and dozens of other publications.

This article originally appeared in the spring/summer issue of Haverford magazine.