Demonstrating Courage: Douglaston Development's Jessica Sherman on Affordable Housing, Social Impact, and Moving Forward
Portrait by Shawn Connell.
By Julia Gamolina
Jessica Sherman serves as Vice President on Douglaston Development’s Affordable Housing team, where she works on the company’s vast array of assets portfolio wide. Currently, Jessica is leading the team’s rehabilitation efforts at the Linden and Penn-Wortman houses in Brooklyn, New York, a $430 million collaboration with The New York City Housing Authority (NYCHA). Jessica also recently founded One Bar Development, where her mission is to support affordable housing by partnering with communities to reimagine their future.
Prior to joining Douglaston Development, Jessica worked as a Leadership Fellow at the Port Authority of New York and New Jersey, focusing on regional infrastructure management and development. Jessica holds an M.B.A. from Columbia Business School, an M.Sc. in Social Policy from the University of Oxford, and a B.A. from the University of Pennsylvania.
Tell me about your foundational years - where did you grow up and what did you like to do as a kid?
Born and raised on Long Island, I grew up with a dad who started his own construction company that evolved into a development and management company. Real estate, building homes, and thinking about where people lived was always part of our family culture. My siblings and I were raised on the idea of community being more than just a place where you lived, it was a new apartment building for working class families, the homes we gathered in with loved ones, and the people and organizations that helped to uplift their neighbors. Most importantly, community was about how we interacted with the people around us.
Giving back was a big part of that. My grandfather, Eddy, ran a pharmacy in Brooklyn and hosted community events that we would all attend every year. One day that meant a lot to all of us was Harrico Kids Day, a holiday festival and parade for children who lived in the neighborhood. The sense of community my grandfather fostered went beyond neighborhood events. The city even renamed the corner of Manhattan Avenue and Greenpoint Avenue “Charno Way” after my grandfather and his brother. When kids shoplifted from the store, they would often hire them to pay off their debt. Those who showed interest became a part of the family, like an ‘aunt’ who my grandfather helped through pharmacy school. The idea of taking care of people around you, understanding what someone was struggling with, and trying to find a solution together was always embedded in how I thought about community.
Also, while I grew up with strong roots in the city, visiting my dad’s construction sites in Manhattan and my grandparents in Brooklyn and Queens — my family lived on Long Island — I loved having access to so much outdoor space. Nature and adventure are still a big part of my family culture today; my husband and I love to take our kids hiking and to the beach. For me, the juxtaposition of the city and the suburbs helped me understand from an early age that where you might live could be decided by factors out of your control and would impact your day-to-day life.
Jessica, wearing a Santa hat, at the annual holiday festival her grandfather hosted for children who lived in Greenpoint, Brooklyn. The event, Harrico Kids Day was a symbol of her family’s strong community ties.
Jessica with her extended family, including her father, brother, cousin, and uncle who work with her at Douglaston Development.
What did you learn about yourself during your time at UPenn and Oxford, and then during your MBA?
Many of my role models growing up had a strong moral compass and sense of community, which inspired me to want to build a career that would in some way contribute to the greater good. I was drawn to the University of Pennsylvania because of the opportunities to take Academically Based Community Service courses that would allow me to interact with the surrounding community. I didn’t want to sit in a room and learn about finance — I wanted to be out in the world working with people.
While I enjoyed the hands-on nature of my classes at Penn, I wondered if the work I was doing was the best use of time and resources. That’s what drew me to the Evidence-based Social Interventions Masters at the University of Oxford. This degree gave me the tools to think more critically about whether government, nonprofit, and other socially-oriented programs were really working as intended. This notion also drew me to Columbia Business School, where I further honed my understanding of not only if these programs worked, but if they worked for the right cost — and where I finally took those finance courses I avoided in college!
I learned through my education that while a commitment to social impact is important, time and resources are limited. I needed to develop the strategic, management, and finance background required to ensure programmatic success. My education helped me pull together the different skill sets I would need to develop and implement innovative solutions at scale to longstanding obstacles.
How did you get your start in the field?
My first job was at a consulting firm, where I worked across the government relations, corporate social responsibility, and business development sectors. Gravitating toward projects that were complex in nature and had a social impact led me to my next job, which consisted of helping to scale a start-up international school that aimed to educate students outside of the borders of its classrooms. While I appreciated the mission and the opportunity to see the world, I missed the pace of my previous work and the connectivity I felt to the people I was serving. I knew I wanted to be working somewhere where I could have a tangible impact, which led me to infrastructure and ultimately affordable housing.
“I am fascinated by how people and things move around the world. The movement of workers, tourists, supplies, and food occurring every day in New York is extraordinary, and most people don’t even think about how transportation is the backbone of our city.”
Tell me how you got to the Port Authority!
As travel has always been a passion of mine, I am fascinated by how people and things move around the world. The movement of workers, tourists, supplies, and food occurring every day in New York is extraordinary, and most people don’t even think about how transportation is the backbone of our city. My interest in how large systems function led me to apply to the Leadership Fellows Program at the Port Authority, a rotational program where I was exposed to multiple departments in the organization. I started out working in the Office of Environmental Sustainability before completing a placement with the Chief Operating Officer. When Hurricane Sandy occurred, I was honored to contribute to the Port Authority’s herculean effort to not only get all bridges, tunnels, and other assets up and running but to also futureproof their systems to prevent future damage. My last project at the Port Authority was my favorite — the public-private partnership to redevelop LaGuardia Airport. The redevelopment was a massive project with local and national impact. It was exciting because of the challenge and possibilities it presented.
When did you finally join Douglaston?
I found my work at the Port Authority meaningful on many levels. I love solving large scale, complex problems that involve diverse stakeholder groups with varying priorities. It wasn’t always easy, but upon completion I could point to something and know I had made a difference. While completing my MBA, I knew that whatever I did next had to have the same impact-driven purpose. I loved interning at Amazon and enjoyed the fast-paced culture, but ultimately knew I wanted to utilize my experience in a more meaningful way. As I considered jobs in impact investing and philanthropy, I realized how much of my passion could be actualized working side-by-side with my dad and my brother, focusing on affordable housing. Once I started considering the possibilities that existed, it was an obvious choice to join my family business. My brother Ben works on the market rate side of our company, and his guidance has been essential to my successes.
My dad has built an impressive platform with talented people who I am fortunate to have as colleagues. As what a business school student would call a ‘career switcher,’ it was important to me that I start as a Project Manager to learn the ropes and forge my own path with the company. I used this time to translate my Urban Studies background, MBA, and infrastructure development and management skills into the affordable housing space.
Jessica and Kendall House on a construction site visit at Vista Winds in Peoria, Arizona
Jessica Sherman and colleagues volunteering with the Fund for Public Housing at the community garden on the grounds of a NYCHA housing project.
Where are you in your career today? What is on your mind most at the moment?
During my first few years at Douglaston Development, I worked on ground-up affordable housing projects in the Bronx and Staten Island. As my role evolved, I identified the kinds of projects that excited me — large scale public-private partnerships similar to the work I was doing at the Port Authority. I love the strategy, creativity, and collaboration that goes into developing a multiphase project or rehabilitating an occupied building.
While I’ve been focused on expanding Douglaston’s preservation business, the first and most important thing on my mind is my kids. I’m always trying to find balance between my career and my family, learning when to lean into work and when to lean into motherhood. Luckily, my husband is good at bedtime!
Looking back at it all, what have been the biggest challenges? How did you manage through a disappointment or a perceived setback?
One of the biggest challenges I’ve faced is balancing collaboration and leadership. My style of work is very collaborative — I try to bring people in and to understand their perspectives — but I also like to move quickly. Moving a project forward while also incorporating different perspectives is a challenge, but it’s so important because the more you incorporate stakeholder voices, the better the outcome of a project. As we’ve partnered with different people internally and externally, disappointment for me has often looked like a difficult relationship – feeling like we aren’t moving in the same direction with the same approach or goals.
I’ve managed through that by leaning on people I respect within our own company as well as mentors and peers to talk through the issues. I also try to be my most authentic self. I’ve learned it’s okay to be vulnerable in the workplace and to try to tackle conflict head on. I’m now comfortable saying, ‘Hey, I’m having a hard time with what’s going on between us, can we talk about it?’ Sometimes someone will want to talk, and sometimes they won’t. The best way for me to get through it is to try to continue to make that connection, to build that relationship, and to make sure that when a project does move forward, it has the buy in it needs to be successful.
“I measure my professional success by the changes in the day-to-day lives of our residents. What we do enables residents to take a new job, send their kid to a better school, or focus on a lifelong dream because of newfound housing security. This kind of opportunity is what makes New York great.”
Wow! That conversation can be so tough to have, but it’s wonderful to hear that you approach a possible resolution head on. That takes courage! Speaking of which, what are you most excited about right now?
Over the last five years, I’ve worked with my team to expand our preservation focus. We just closed a nearly 2,000-unit preservation project at Linden Houses and Penn-Wortman in East New York in partnership with NYCHA, L+M, Dantes Partners and SMJ. Moving that through construction and conversion is my biggest priority. This project is especially meaningful to me because my dad, Jeff Levine, actually grew up in the Linden Houses for a portion of his childhood. Working with NYCHA, our partners, and the Linden and Penn-Wortman residents to bring much-needed renovations to both sites is important and exciting.
I'm also very excited that I recently launched my own development company, One Bar Development. I plan to continue building on my passion for working with community partners to help reimagine their own futures and create housing opportunities that we can be proud of.
Most of all, I’m excited and hopeful that we will start moving into a world where we understand how to live with COVID. This will allow so much of the hands-on work we do in affordable housing to be reignited. It’s been hard to develop relationships with residents and communities that are so important to our work because of the constraints the pandemic placed on our ability to gather in person. Resident health and safety remain my biggest priority, but as we continue to move into our new reality and become more comfortable with the ways we can still engage, there are opportunities for us to work better together and to learn more about the people we are working with.
Who are you admiring now and why?
I admire some of my peers in the industry who have been brave enough to start their own companies and take risks on their own, which is really what inspired me to start One Bar. I have several friends who, whether they started their own company or just made a career switch that felt right, demonstrated their courage by taking risks. They have inspired me to do the same.
I also admire so many of the residents and community stakeholders we work with on our new construction and rehabilitation projects. These residents are committed to bringing positive change to their communities not just for themselves, but for their current and future neighbors. Their knowledge, insight, and willingness to come to the table and collaborate is the reason I am excited to begin working alongside them on projects at One Bar.
Jessica and her family on Long Island.
Jessica and her family on a hike in Arizona.
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’d like to think that in some small way, and hopefully a few large ones, the world is a better place than it was before I was here! While I hope my work does have large scale impact, what matters most to me is that what I am doing positively affects someone or improves their life in a way that is meaningful to them. My core mission is to wake up each day proud of what I did the day before and excited by the ways I can expand upon it. I love making new connections and identifying new solutions.
I measure my professional success by the changes in the day-to-day lives of our residents. What we do enables residents to take a new job, send their kid to a better school, or focus on a lifelong dream because of newfound housing security. This kind of opportunity is what makes New York great. With the right ingredients, anything is possible here.
Personally, my parents did an excellent job of ensuring their children understood kindness and compassion. My greatest success would be to impart those same values to my own children. I can’t wait to support them through the choices they make on their own paths.
Finally, what advice do you have for those starting their career? Would your advice be any different for women?
Lean into what you’re afraid of. It’s easy to stick with what we know, are good at, and are comfortable with. But early in your career you have this unique opportunity to take risks and fail, and you should use that chance to try something out that might not be your strong suit or that you aren’t sure about. Taking these risks enables you to expand your toolbox, and you’ll be surprised at how often the skills you learn will help you later in your career. I think that advice is even more so important for women.