Public Service: Work for America's Caitlin Lewis on Local Government, Multifaceted Projects, and Making Cities Work for Their People
By Julia Gamolina
Caitlin Lewis is the Executive Director of Work for America, a new nonprofit initiative working to make public service a more desirable, accessible, and stable career path that uplifts families, communities, and our country.
Caitlin’s career spans the public, private, and non-profit sectors. She has developed social impact strategies for global brands and served as a philanthropic advisor to Van Jones. She was a founding employee at an affordable housing fund and Chief of Staff at a mission-driven govtech company. She has served in local, state, and federal government, including at New York City Hall and in the White House Liaison Office of USDA. She has worked on political campaigns and ran external affairs for the organization that manages Times Square. Caitlin earned a B.A. in Social Studies from Harvard University and is a graduate of Coro Leadership New York.
JG: You just started as Executive Director with Work for America— congratulations! What will you be focused on for the coming year, and what should our readers be paying attention to most in this realm next year as well?
CL: I’m thrilled to be working on one of the most urgent problems facing American cities: a public sector staffing crisis that could make or break everything—from the delivery of desperately needed affordable housing to once-in-a-generation infrastructure projects that we all rely on for clean water, robust transportation and more.
For those of you who care about the built environment, urban planning, and mission-driven real estate, there’s honestly nowhere cooler—or more impactful—to do that work than in local government. You get to shape policies and projects that will define your community for decades. Even more important, when governments are fully staffed, cities thrive. When they’re not, projects get delayed, budgets spiral, and that impacts everyone.
At Work for America, we’re working to make public service a desirable and stable career path. My mission is to make sure key roles—like city planners and housing coordinators—aren’t lured away by private sector jobs, but instead are driving real change in our communities. Over the next year, I’ll be focused on getting all of you to consider a career in local government—because that’s where the magic really happens.
City Hall Team, courtesy of Caitlin Lewis.
Now let's go back a little bit—you studied social studies at Harvard. What were you hoping to learn and do in the world?
I actually started as a math major, with the goal of becoming a behavioral economist. My freshman fall, I took a very difficult math class—the kind where we were working in the 34th dimension, literally. I was the only freshman in the course, and from day one, I just couldn’t wrap my head around the concepts. After the first exam I was failing, despite working my butt off at office hours and study groups. It was one of those classic Harvard moments—when you realize that you’re surrounded by hundreds of people who were at the top of their high school class. It felt intimidating and scary.
Around the same time, I had the incredible opportunity to serve as a “liaison” to Stephanie Cutter during her fellowship at the Institute of Politics. She had just left the Obama campaign, where she was Michelle Obama’s chief of staff, and I think she took a liking to me because I was both clueless and shamelessly curious—in our first conversation, she mentioned David Axelrod, and I asked “Who’s that?” One day, over a meal, she asked me how I was doing—really doing. I burst into tears and confessed that I was failing math and didn’t know what to do. She just shrugged and said, “I had the exact same experience my first year of college. I switched majors, and I think it worked out fine.” Understatement of the millennium! So, I switched majors to social studies and never looked back.
My social studies professor, Bo-Mi Choi, was a brilliant woman and became a close mentor. She taught me how to think critically and tangibly apply the social theory from class to my own life. So, to answer the question—when I crash-landed at Harvard, I had no idea where I was headed or why, but social studies taught me how to slow down, think critically, and ask the tough questions of myself that have kept me grounded.
“In any complex project, especially ones involving diverse stakeholders, you’re never going to make everyone happy. If you’re only making one side happy, you’re probably not doing what’s best for the public.”
You then worked in DC, in Philadelphia, and eventually came to New York City, where you worked in various roles. Tell me about the take aways for some of those roles that you still bring to what you do today.
In DC, I worked at USDA, where I spent most of my time organizing trips to state fairs for Cabinet members. It was right after the 2008 recession, and we branded it “Recovery Act Summer—on a stick!” I was nineteen years old, working directly with Cabinet secretaries’ teams and USDA officials on the ground, coordinating high-profile events. It was my first real taste of government, and I fell in love. I discovered that if you’re young and hungry and willing to work hard, you can step into roles that feel far beyond your years.
When I landed in New York City, I took a job with the Times Square Alliance. I was horrified at first that my cool New York friends would never take me seriously working for Times Square. But very quickly, I realized there’s no place more quintessentially New York than Times Square. My job covered the highs and lows —from optimizing trash pickup in a neighborhood with 500,000 people traversing it every day, to coordinating the New Year’s Eve ball drop for a million people. It made me fascinated with how complex urban spaces function and how much thought and dedication go into doing it well. After that, I was desperate to work in city government and see how things worked from the inside.
City Hall gave me that chance. I worked on some incredible projects like the East Midtown rezoning and the transformation of Governors Island. I also had the opportunity to launch women.nyc, an initiative that connected female entrepreneurs across all five boroughs. What I loved most about City Hall was being able to take ownership of these massive, multifaceted projects and work alongside some of the smartest, most dedicated people I’ve ever met. That experience made me realize that when you get the right team in place, you can truly make cities work for people—and that’s so much of what underlies my work at Work for America.
Times Square New Year’s Eve. Courtesy of Caitlin Lewis.
Looking back at it all, what have been the biggest challenges? How did you both manage through perceived disappointments or setbacks?
I often think back to my time leading the rezoning of East Midtown Manhattan—a project the prior administration had tried but couldn’t get over the finish line due to community opposition. We took another stab at it, after an extensive community engagement process and outreach to every stakeholder group imaginable. One of the more controversial aspects was related to air rights transfers. We landmarked a significant number of buildings and religious institutions as a part of the rezoning, and we allowed those institutions to sell their air rights to any sites throughout the neighborhood rather than limiting the sales only to the immediately adjacent properties. But, we also instituted a tax on each square foot of air rights sold to fund public realm and transit improvements.
After careful analysis, we set a price that we believed would support both new commercial development and community benefits. It felt like a win. But the day we finally passed the rezoning? Developers and owners of the landmarked buildings were mad about the price of the air rights tax. Instead of getting praise for doing something bold, thoughtful, and community-driven, we got a lot of grumbling. I was gutted.
That’s when my boss, Deputy Mayor Alicia Glen, pulled me aside and said, “Welcome to the life of a public servant. If all sides are a little pissed off, you did a great job.” And she was right! The rezoning has led to more commercial development than we could have imagined, with new public realm projects springing up every day, funded by those very developments. I carry that lesson with me wherever I go: in any complex project, especially ones involving diverse stakeholders, you're never going to make everyone happy. If you're only making one side happy, you’re probably not doing what’s best for the public.
“Forget what everyone says you should do. Take the time to figure out what feels meaningful to you. The risk is worth it, and you’ll thank yourself later for finding a path that’s truly yours.”
What have you also learned in the last six months?
Work for America was a one-person organization up until September, so I’ve recently been learning how to adjust my areas of focus as our team grows. I love substance—I can nerd out for hours on the details of a complex problem like the public sector staffing crisis. But I’m realizing that’s not always my role anymore! With an incredible Head of Programs, Shifra Goldenberg, now on board, I’ve had to embrace the reality that if we’re going to move as fast as we need to and reach the ambitious goals we’ve set—which feel absolutely urgent given how much support governments and communities need—we have to divide and conquer.
I’m also adjusting to being more externally facing. I’ve always been the “Number Two," working behind the scenes for brilliant, fast-moving people—ghostwriting, solving problems, and keeping the agenda on track. Now, I’m the one who has to step out front and say the words I’ve been writing all these years! It’s a change, but an exciting one.
Who are you admiring now and why?
NYC government is tough on the best days, and right now, it’s harder than ever. I’m in awe of the public servants who have stepped up during this extremely turbulent time. Maria Torres-Springer, the new First Deputy Mayor, has been a critical stabilizing force, ensuring that thousands of public servants can continue their work, despite the challenges. I’m grateful to her and the many others working tirelessly on behalf of all New Yorkers.
women.nyc launch. Courtesy of Caitlin Lewis.
What is the impact you’d like to have on the world? What is your core mission? And what does success in that look like to you?
I want to make government work for everyone. I had so much fun working in government, and now I want to help inspire and empower people across the country to do the same—and to see the direct impact of their work on their communities. That’s what success looks like to me: public servants seeing the results of their efforts in safer streets, vibrant public spaces, and a government that truly delivers.
Finally, what advice do you have for those starting their career? Would your advice be any different for women?
Forget what everyone says you should do. Take the time to figure out what feels meaningful to you. The risk is worth it, and you’ll thank yourself later for finding a path that’s truly yours. 31% of my graduating class went into finance or management consulting—far more than government, nonprofits, arts, and research combined. And while I knew finance wasn’t for me, I didn’t really know what was for me. I moved to NYC without a job and it was terrifying. At times, I felt like a failure for graduating from Harvard without a clear next step. But if I hadn’t done that—if I hadn’t lived with my friend’s parents (shoutout to Marla and Chip!), nannied, and hustled to find the job that excited and inspired me—I wouldn’t be where I am today.