The startup CEO remaking City Hall

If you think of Michelle Wu as the architect of Boston’s new city government, then Tiffany Chu ’10 might be the general contractor. As the chief of staff to Mayor Wu, Chu is in charge of figuring out how visions of urban transformation actually take shape.

Take the Thursday afternoon in early February that found Chu at a mahogany conference table in City Hall, where she spends most of her days. She was meeting with heads of the department of innovation and technology to discuss a significant obstacle: it was taking as long as six months to get department openings posted to the city’s website, and even longer to actually hire people such as qualified software developers. The delay in hiring was slowing down plans to improve Boston’s 311 app (which lets residents and visitors report non-emergency issues, like potholes and graffiti) and other digital tools that would make it easier for Bostonians to access services, which was one of the mayor’s goals.

This wasn’t acceptable to Chu and her colleagues, including the CIO, the chief digital officer, and the chief data officer. A series of redundant checks and approvals by different agencies seemed to be the main culprit holding up job postings. Chu, who oversees daily operations and long-term initiatives within the mayor’s office, wondered why more of the process couldn’t be standardized. Would an interdepartmental task force clear the choke points? Did she need to dedicate someone to a fix? Leaning over her lunch—a bowl of veggies and rice brought from home—Chu told her fellow leaders that the mayor was eager to report new accomplishments wherever possible. A faster hiring process could be one such win.

A few days later, Chu reflected on that meeting as an example of a struggle she encounters a lot in local government: striking a balance between a good experience for residents and the rules and restraints inherent in the public sector.

Before her time, the city government went overboard with “the number of checks and balances we put in place to prevent X, Y, Z terrible disasters from happening,” she says. “We need to peel back the layers and figure out what is most important.”

A bit of history: Michelle Wu took office in November 2021 after a rousing campaign that drew national attention for its uber-progressive and urbanist ideals, ending in a landslide victory against a more moderate opponent. A former city councilor and a protégée of Senator Elizabeth Warren, Wu promised voters sweeping changes such as fare-free public transit, an overhaul to the city’s development agency, and a Boston-wide Green New Deal. At age 36, she became the first woman, first Asian-American, and first person of color to be elected Boston’s mayor.

On the other side of the country, Chu was also having a very big year. Remix, the civic tech startup she’d cofounded in 2014, had been acquired in March 2021. By fall, Chu was still shifting from her previous role as Remix’s CEO into one as senior vice president at Via, the new parent company. She was also settling into her new home in Seattle, having recently moved from San Francisco, the city she’d lived in for years and where she’d once served as an environmental commissioner.

Chu had watched with admiration from the West Coast as the Wu Train (to use a favorite phrase of the mayor’s supporters) gained steam. As an MIT graduate, she kept a fond eye on Boston news, and she was inspired by Wu’s vision for the city. While she didn’t personally know Wu, she felt a connection as a fellow Taiwanese-American woman with immigrant parents. “I’d been fangirling from afar,” Chu remembers. “My mom would send me newspaper clippings about her every so often.”

Supporting the mayor can mean helping her prepare for the State of the City address or selecting gifts for visiting British royalty. One day is rarely like the next.

Then came a call that would change her life again. It was Mitchell Weiss, who’d been chief of staff to former Boston mayor Thomas Menino and was now helping Mayor Wu’s transition team. He’d known of Chu from using Remix as a case study in a class he taught at Harvard Business School. As Weiss later told the Boston Globe, he thought she had the perfect résumé to be Wu’s right hand, with her “real, true passion for cities and especially for Boston, real experience leading teams and rallying them through big challenges, and real expertise at the intersection of mobility, climate, economic opportunity, technology, and the like.”

It was not the obvious move for a person of Chu’s professional stature. Remix had just sold to Via for $100 million, the kind of deal that would have some tech executives happily settling into a more leisurely existence. But Chu isn’t the average startup CEO.

She and her cofounders had conceived the idea for Remix while she was on a Code for America fellowship, a program that pairs promising young tech thinkers with government agencies to tackle real social problems. The company makes a digital platform that helps public transit agencies map and redesign their networks to improve service and efficiency. Among the hundreds of local governments that use its products globally, the company has built a proven track record of actually making cities work better. (This is not something that can be said of all urban tech companies, to take ride-hailing businesses as an example.)

Chu’s background further testifies to her urbanist bona fides. Before Remix, she had stints as a user experience designer at Zipcar, working on New Orleans’s post-Katrina recovery effort, and writing for Dwell magazine. As an undergraduate at MIT, she’d studied architecture, but she realized she was interested in urban design beyond the scale of individual buildings. She fell in love with cities themselves: their form, their function, their flow. Although she has access to a city fleet vehicle, she’s an ardent cyclist and has often said she hopes never to own a car. So far, so good—for her, Boston’s walkability has always been one of its biggest draws.

Translating this passion for cities into workable ideas to improve them, though, takes a certain finesse. And according to her colleagues, Chu possesses both the strategic-­thinking talents and the people skills to actually move needles.

“She’s really good at asking questions and listening, building empathy with people she works with, and helping us get a better understanding of the world we’re in,” says Dan Getelman, a Remix cofounder and its current chief technology officer. “She’s very driven, and down to figure out what it takes to do what needs to be done and do it.”

Chu hadn’t been looking to leave Remix or Via, and it took her a few weeks to decide to take up Weiss’s offer. Ultimately, she felt it was a once-in-a-lifetime opportunity to help Wu make the kind of urban change that both women strongly believe in, and in a city she truly loves.

COURTESY OF TIFFANY CHU

She started in the spring of 2022 and quickly learned that building a new administration was hard, at times chaotic work. It was a lot like her time leading a startup, in fact; her main focus was putting together a leadership team and crafting the right organizational processes to support the mayor’s ambitions. Chu compares that first year to “building the plane as you’re flying it.” But she’s proud of what she accomplished—namely, hiring for cabinet positions that never previously existed, such as the city’s chief of planning, Arthur Jemison, as well as its deputy chief of urban design, Diana Fernandez Bibeau, and director of green infrastructure, Kate England.

“I know people don’t always think of city government as the place to go for the best talent,” she says. “But I think we’ve overcome a lot of that, and have built a truly world-class leadership team that both has Boston roots and can bring in new insights.”

There are fundamental differences between running a company and running a city, however. In the private sector, success can be measured in revenue and customer growth. But in a young mayoral administration—especially one that promises transformation within an organization that is built to move slowly—clear-cut wins can be somewhat elusive. Observers of Boston politics note that this may be one of the Wu administration’s central challenges. With all her campaign pledges, the mayor “essentially told voters to raise their expectations of what’s possible for city governments to achieve,” Abdallah Fayyad wrote in the Boston Globe in January 2022. While Wu’s State of the City address in January 2023 highlighted several accomplishments, her marquee campaign promises, such as eliminating transit fares and dismantling the Boston Planning & Development Agency, are yet to be realized.

“It’s going to take time to see those wins when you do it the right way,” says Daniel O’Brien, a professor of public policy at Northeastern University and the director of the Boston Area Research Initiative. “But I think that means her administration will need to be strategic in being able to highlight progress for us.”

Wu’s pledge to make climate change a key priority through a Green New Deal is one of those tricky areas. In another meeting that afternoon in February, Oliver Sellers-Garcia, who holds the title of Green New Deal director, was worried about how best to communicate with the public about progress on the initiative, given that the city has not released a unified plan for it. Some colleagues wanted to see a splashy news announcement. Chu told him not to worry about that, and encouraged him instead to promote the city’s existing efforts to reduce fossil-­fuel use, including its plans to decarbonize new construction and expand EV charging. Behind-the-scenes implementation work may not always earn the kind of press attention that many politicians crave, but Chu sees it as the main job of city government. It’s a balance that can be hard to strike.

To use a City Hall catchphrase, Chu is constantly “changing altitude”: sometimes zeroing in with staff on down-to-earth details, other times generating new concepts and pie-in-the-sky ideas with the mayor. She and Wu are in constant communication and they regularly block off time in their ever-changing calendars for both brainstorming and tactical discussions. Sometimes supporting the mayor means helping her prepare for the State of the City address; other times it means selecting gifts for visiting British royalty. One day is rarely like the next, and there are plenty of late nights.

Chu joined local government at a particularly tough moment for cities everywhere. Some of Boston’s most significant problems—an affordable-housing crisis, an ongoing pandemic, and a changing climate—are in many ways beyond the control of the mayor’s office. Boston is also not immune to the recent rise in harassment and threats toward public officials, as well as an uptick in hate and racist attacks against the Asian-American and Pacific Islander communities. Chu considers it part of her job description—and the mayor’s—to shine a light on these challenges.

Is being chief of staff a job for anyone? Definitely not. But is it gratifying for Chu? Absolutely. She even says it’s fun. Her goal is always the same, she says: “Are we pushing the envelope around what is possible, and pushing that forward in a way that the city couldn’t do before? Are we redefining what the status quo is, and qualitatively making life better for residents than before?” One day at a time, Chu is trying to build the answers.