Transforming Places: Jamestown's Carrie Denning Jackson on the Evolution of Cities, Innovation Strategy, and Being Hyper-Critical
By Julia Gamolina
Carrie Denning Jackson is Vice President, Innovation Operations of Tech & Innovation at Jamestown. Prior to joining Jamestown, Carrie was a Director on the Development team at Sidewalk Labs, Google’s urban innovation company, where she was responsible for ground floor development and innovation strategy. She originally joined Sidewalk Labs as Chief of Staff. Carrie is a member of ULI Technology and Innovation Council and a board member of Plan A Health. She has a Bachelor of Arts, Master of Arts, and Master of Business Administration from Stanford University. In her interview, Carrie talks about innovation in cities and making transformative places, advising those just starting their careers to find their mentors and sponsors.
JG: Tell me about your foundational years - where did you grow up and what did you like to do as a kid?
CDJ: I grew up in Greenwich, CT, but my dad is originally from Utah and my mom, as the daughter of an Air Force colonel, lived in something like eight states growing up. They expected A’s and hard work, exposed us to lots of people and places, and it’s really from them that I learned to work my tail off.
Looking back it’s pretty obvious that I was hooked on cities and places from the get-go. As a kid, I loved taking Metro North into the city. I can still remember deconstructing my Playmobil dollhouses at home just to reassemble them into high rises.
I also played a lot of sports growing up. I think that was the start of my appreciation for being part of a team and the energy that develops when you’re in the trenches together. Never underestimate camaraderie in getting projects over the line.
“I was able to spend a summer working in Mumbai on their metro rail. This was eye-opening - the challenges were so different than those in the U.S. - and the people were great.” Courtesy of Carrie Denning Jackson.
All of your schooling was at Stanford! What did you learn about the world, and about yourself, through the various programs you were a part of?
In college, convinced that I would eventually go into the arts, I decided to major in Art History. It wasn’t until the fall of my sophomore year that I took a seminar called Extreme Architecture, taught by Maria Gough. It dove into the history of utopian planners and their visions for the perfect city, covering everyone from Bruno Taut to Le Corbusier to Archigram and Superstudio. I was hooked.
I learned the term “urban planning,” and it was in that class that the idea of becoming a city planner first hit my radar. There was a grad student in the class, Alex, who wrote his final paper on cities and the internet — comparing the decentralized cities of Archigram and Constant Nieuwenhuys with today’s internet. This was another watershed moment for me. The interplay between a virtual internet and our physical cities became somewhat of an obsession. This has stayed with me — from my college thesis on how electronic trading influenced the physical NYSE to Sidewalk Labs to my work now bringing innovation and technology to Jamestown LP.
For me, getting an MBA was about acquiring a toolkit. I was missing the basics of finance, economics, even sales — which, as my current manager recently pointed out, is a crucial skill for “selling” innovation within Jamestown. While I knew I would like the content of the classes more in planning school, I knew I needed a business degree to be effective in this space — even if I didn’t yet fully grasp its practical applications day-to-day.
How did you get your start in working with the built environment?
Good question. It’s hard to pinpoint a moment because everything since that class has been about cities and innovation for me. That field didn’t quite exist when I graduated, however. I was also looking for a job just as the financial crisis hit, so opportunities were limited. Luckily, I found a role at a research lab at Stanford, where we used Geographic Information Systems (GIS) to tell stories. It was here that I learned how powerful GIS is, and how maps and infographics be used.
“My work has serendipitously evolved with a burgeoning industry. As I went through my 20s, the whole concept of ‘smart cities’ was evolving. While I don’t like the phrase — cities have never been ‘dumb;’ they’ve always responded to the technologies of the moment, from steam engines to electricity — I’m really grateful that this has been such a ‘right place, right time’ situation.”
Tell me how your work evolved, and you with it.
My work has serendipitously evolved with a burgeoning industry. As I went through my 20s, the whole concept of “smart cities” was evolving. While I don’t like the phrase — cities have never been “dumb;” they’ve always responded to the technologies of the moment, from steam engines to electricity — I’m really grateful that this has been such a “right place, right time” situation. And I’ve been able to lean on so many people to help get me here.
Where are you in your career today? What is on your mind most at the moment?
Today, I feel like I’m in a good spot. I love my job. I get to seek out truly brilliant innovations and quickly learn how to incorporate them into what I believe is one of the best real estate companies around. The people are smart and the places they create are extraordinary. There is also an exciting network of thinkers and doers in this space that I constantly find myself tapping into for ideas and advice. Many of them have become close friends, and it really underscores how much I love what I’m doing.
There are a lot of things on my mind right now, but sustainability and inclusion are at the forefront. Construction and building operations are a significant source of carbon emissions. What can those of us who work in the built environment do to help? It turns out that there’s a lot that we know how to do right now. Nicole LeBlanc at 2150 VC put it well — getting closer to zero carbon will require a lot of little incremental changes — and she’s right. But I’m optimistic that those changes will add up sooner than we may realize.
“Walking the Hearn with Andrew Staniforth, now CEO of Assembly OSM. It’s amazing seeing where people have ended up after Sidewalk Labs.” Photography courtesy of Laura Capucilli.
The industry is also finally addressing the massive equity issues in real estate and urban planning. I don’t just mean internally with low representation of women and people-of-color in the field. There has been a reckoning underway regarding the industry’s role in gentrification, redlining, hollowing out what were once close-knit neighborhoods, and setting up some very entrenched, systemic challenges for the residents there. This is starting to change: real estate and urban planning are now being held accountable, and that’s a great thing.
That said, we’re still trying to figure out the right approaches, and I constantly try to think about implications further down the line. Looking back through history — for example, affordable housing in the 1960s and 1970s — there have been so many well-intentioned policies that end up backfiring. I’m often reminded of Alain Bertaud’s book Order without Cities: How Markets Shape Cities. He does an excellent job outlining this dilemma. He and his research assistants mapped out where it was actually feasible to build affordable housing in Mexico City, and after applying all of the city’s — usually well-intentioned — regulations. It was virtually impossible. I try to constantly layer in these critiques. It’s easy to be captivated by a utopian vision, and it’s important to be hyper-critical and think through implication after implication.
Looking back at it all, what have been the biggest challenges? How did you manage through a disappointment or a perceived setback?
My most challenging role was becoming chief of staff at Sidewalk Labs. Dan Doctoroff is one of those dynamic leaders who raises the bar and holds you to a higher standard. That position prepared me for pretty much anything.
In terms of managing through setbacks, the key is managing yourself. Feedback is hard. I don’t believe anyone when they say it’s easy to digest. Disappointments are hard. Not moving ahead with Toronto, for example, was really challenging to take. My husband and I relocated there for a year, and it’s not easy to live and work in a city on such a controversial project. Exercise has kept me sane through all of this. Sometimes you just need to throw a medicine ball at a wall 50 times to get back to a good baseline. I also try to meditate twice a day.
“The industry is also finally addressing the massive equity issues... there has been a reckoning underway regarding the industry’s role in gentrification, redlining, hollowing out what were once close-knit neighborhoods...real estate and urban planning are now being held accountable, and that’s a great thing. ”
What are you most excited about right now?
The potential that exists in this area. With cities, it feels like the entire space has exploded over the past few decades. Early on it was things like Four Square, IBM, and people like Anthony Townsend critiquing the “smart” cities space. But now it’s an entirely new world. Uber, Postmates, Opendoor, Essussu, Xeal, Assembly OSM, Lyft, Lime. And that’s only barely scratching the surface. It’s a different world and excellent talent and capital are flooding into proptech.
I’d also be remiss if I didn’t mention my excitement around my current role. Jamestown is a company that transforms places. To be able to now drive their innovation strategy and deploy those technologies across the company is just the best.
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?
My goal in life is to make places people want to be in, and constantly keep them exciting by bringing in new ideas. To that end, I love constantly learning and bringing my best to what I do.
“I’m now responsible for a little New Yorker, it’s the best. He loves the subway, so I think we’re off to a good start.” Courtesy of Carrie Denning Jackson.
Finally, what advice do you have for those starting their career? Would your advice be any different for women?
Find mentors and sponsors. Seek both out and know the difference — there is one! The research shows this is much harder for women and people of color. If you can, work at a place that recognizes that and works to rectify it. And, when you’re at that place, go out of your way to mentor and sponsor those around you. Recognize when others are doing well, and make sure to highlight their work to their manager.
Don’t expect to have your dream job right out of school. I was thirty when I started working at Sidewalk, and one day, looked up and realized I was in my dream job. Focus on putting your head down, getting good at what you do, and putting out good energy, first and foremost.
Finally, become friends with every executive assistant you cross paths with. They keep the company together, and they deserve a lot of respect.